ORCID Profile
0000-0002-3834-7398
Current Organisation
University of Queensland
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Research Topics
In Research Link Australia (RLA), "Research Topics" refer to ANZSRC FOR and SEO codes. These topics are either sourced from ANZSRC FOR and SEO codes listed in researchers' related grants or generated by a large language model (LLM) based on their publications.
Top 5 Research Topics
ANZSRC Field of Research (FoR)
Organic Chemistry | Organic Chemical Synthesis | Organic Chemical Synthesis | Natural Products Chemistry | Biological And Medical Chemistry | Medicinal and Biomolecular Chemistry | Biologically Active Molecules | Medical and Health Sciences not elsewhere classified | Structural Chemistry | Synthesis Of Macromolecules | Separation Science | Analytical Spectrometry | Genetics | Chemical Characterisation of Materials | Plant Protection (Pests, Diseases And Weeds) | Other Chemical Sciences | Analytical Biochemistry | Environmental Chemistry (incl. Atmospheric Chemistry) | Medicinal and Biomolecular Chemistry not elsewhere classified | Analytical Chemistry | Bioinorganic Chemistry | Agricultural and Veterinary Sciences not elsewhere classified | Characterisation of Biological Macromolecules | Separation Science | Transition Metal Chemistry | Inorganic Chemistry | Physical Chemistry (Incl. Structural) | Electrochemistry | Proteins and Peptides | Gene Expression |
ANZSRC Socio-Economic Objective (SEO)
Expanding Knowledge in the Chemical Sciences | Chemical sciences | Treatments (e.g. chemicals, antibiotics) | Expanding Knowledge in Technology | Forestry | Plant Production and Plant Primary Products not elsewhere classified | Primary products from plants | Field crops | Inorganic Industrial Chemicals | Organic Industrial Chemicals (excl. Resins, Rubber and Plastics) | Cancer and Related Disorders | Prevention—biologicals (e.g. vaccines) | Health not elsewhere classified | Plastics in primary forms | Essential Oils (e.g. Tea Tree, Eucalyptus, Lavender, Peppermint, Boronia, Sandalwood) | Animal Protection Chemicals | Crop Protection Chemicals | Industrial Energy Conservation and Efficiency | Human Pharmaceutical Treatments (e.g. Antibiotics) | Expanding Knowledge in the Environmental Sciences | Expanding Knowledge in the Biological Sciences
Related Links
Publications
Wasabi (Eutrema japonicum) Reduces Obesity and Blood Pressure in Diet-Induced Metabolic Syndrome in Rats
Publisher: MDPI AG
Date: 29-10-2022
Abstract: 6-(Methylsulfinyl)hexyl isothiocyanate (6-MSITC) has several biological functions. The present study aimed to evaluate the composition of hydroponically grown Tasmanian wasabi (Eutrema japonicum (Miq.) Koidz.) for 6-MSITC in all plant tissues and investigate the influence of wasabi (rhizome and stem blend) in high-carbohydrate, high-fat (H) diet-fed rats. Male Wistar rats were fed either a corn starch (C) or H diet. After the initial 8 weeks, half of the animals on the C and H diets were given 5% (w/w) wasabi powder in their respective diets for an 8-week duration (CW and HW). The control animals received diets without supplementation throughout the 16-week experiment. Our findings demonstrated that wasabi grown under hydroponic conditions contained 6-MSITC in all parts of the plant such as the stem, leaf and flower, as well as the commonly used rhizome, albeit at lower concentrations. Rats treated with wasabi showed reductions in body weight (H, 460.0 ± 9.5 HW, 416.0 ± 3.6 g), fat mass (H, 178 ± 14 HW, 120 ± 23 g), plasma triglycerides (H, 1.7 ± 0.3 HW, 0.9 ± 0.3 mmol/L) and total cholesterol (H, 1.5 ± 0.1 HW, 1.0 ± 0.04 mmol/L), and the plasma activities of aspartate transaminase. Systolic blood pressure and the area under the curve of blood glucose concentration were decreased by wasabi treatment. Thus, wasabi may be a novel alternative treatment to assist in the management of obesity and related metabolic disorders.
1,4-Diazacubane crystal structure rectified as piperazinium
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CC06272F
Abstract: The only reported synthesis of a [ n ]-azacubane, 1,4-diazacubane, on re-examination revealed a disordered piperazine that constitutes the previously reported Ni 2+ Kagome metal organic framework (MOF).
Bridgehead Arylation: A Direct Route to Advanced Intermediates for the Synthesis of C-20 Diterpene Alkaloids
Publisher: American Chemical Society (ACS)
Date: 28-08-2003
DOI: 10.1021/OL0353060
Abstract: [reaction: see text] Rapid access to the ABCE ring system of the C(20) diterpene alkaloids was achieved by silver(I)-promoted intramolecular Friedel-Crafts arylation of a functional group-specific 5-bromo-3-azabicyclo[3.3.1]nonane derivative.
Nitric oxide modulates μ‐opioid receptor function in vitro
Publisher: Wiley
Date: 14-04-2019
Abstract: Painful diabetic neuropathy (PDN) is a type of peripheral neuropathic pain that develops as a consequence of prolonged hyperglycaemia-induced injury to the long nerves. Apart from pain, PDN is also characterized by morphine hyposensitivity. Intriguingly, in streptozotocin (STZ)-induced diabetic rats exhibiting marked morphine hyposensitivity, dietary administration of the nitric oxide (NO) precursor, L-arginine at 1 g/d, progressively rescued morphine efficacy and potency over an 8-week treatment period. In earlier work, single bolus doses of the furoxan nitric oxide (NO) donor, PRG150 (3-methylfuroxan-4-carbaldehyde), evoked dose-dependent pain relief in STZ-diabetic rats but the efficacious doses were 3-4 orders of magnitude higher in advanced diabetes than that required in early STZ diabetes. Together, these findings suggested a role for NO in the modulation of μ-opioid (MOP) receptor signalling. Therefore, the present study was designed to assess a role for NO released from PRG150, in modulating MOP receptor function in vitro. Here, we show an absolute requirement for the MOP receptor, but not the δ-opioid (DOP) or the κ-opioid (KOP) receptor, to transduce the cellular effects of PRG150 on forskolin-stimulated cAMP responses in vitro. PRG150 did not interact with the classical naloxone-sensitive binding site of the MOP receptor, and its effects on cAMP responses in HEK-MOP cells were also naloxone-insensitive. Nevertheless, the inhibitory effects of PRG150 on forskolin-stimulated cAMP responses in HEK-MOP cells were dependent upon pertussis toxin (PTX)-sensitive G
Plant Growth Regulator Daminozide Is a Selective Inhibitor of Human KDM2/7 Histone Demethylases
Publisher: American Chemical Society (ACS)
Date: 11-07-2012
DOI: 10.1021/JM300677J
University of Queensland–National University of Singapore Joint Symposium
Publisher: CSIRO Publishing
Date: 2009
DOI: 10.1071/CH09389
Total Synthesis of (±)-Vibsanin E
Publisher: CSIRO Publishing
Date: 2009
DOI: 10.1071/CH09267
Abstract: Vibsanin E (1), a structurally rare complex diterpene, consisting of a compact 3-oxatricyclo[6.3.2.05,10] tridecane core and an unprecedented 3,3-dimethylacroyl enol ester functional group, formulate a considerable synthetic challenge. Williams and Davies failed to independently synthesize this nemesis, however, a ‘two heads are better than one’ approach delivered the first total synthesis of the molecule, since its diamond aniversary isolation.
Commercial AHAS-inhibiting herbicides are promising drug leads for the treatment of human fungal pathogenic infections
Publisher: Proceedings of the National Academy of Sciences
Date: 24-09-2018
Abstract: Human fungal pathogens resistant to conventional therapeutics pose a major threat to global human health. Thus, there is an urgent need to discover new antifungal drugs that act via novel mechanisms of action. Here, we show that commercial herbicides that inhibit acetohydroxyacid synthase (AHAS) have potent and broad-spectrum antifungal activity in vitro and that chlorimuron ethyl, a member of the sulfonylurea herbicide family, has antifungal activity in a mouse model. Thus, this study shows that AHAS inhibitors have strong potential to be developed into potent antifungal therapeutic agents.
Structural basis of resistance to herbicides that target acetohydroxyacid synthase
Publisher: Springer Science and Business Media LLC
Date: 11-06-2022
DOI: 10.1038/S41467-022-31023-X
Abstract: Acetohydroxyacid synthase (AHAS) is the target for more than 50 commercial herbicides first applied to crops in the 1980s. Since then, 197 site-of-action resistance isolates have been identified in weeds, with mutations at P197 and W574 the most prevalent. Consequently, AHAS is at risk of not being a useful target for crop protection. To develop new herbicides, a functional understanding to explain the effect these mutations have on activity is required. Here, we show that these mutations can have two effects (i) to reduce binding affinity of the herbicides and (ii) to abolish time-dependent accumulative inhibition, critical to the exceptional effectiveness of this class of herbicide. In the two mutants, conformational changes occur resulting in a loss of accumulative inhibition by most herbicides. However, bispyribac, a bulky herbicide is able to counteract the detrimental effects of these mutations, explaining why no site-of-action resistance has yet been reported for this herbicide.
The furoxan nitric oxide donor, PRG150, evokes dose-dependent analgesia in a rat model of painful diabetic neuropathy
Publisher: Wiley
Date: 25-08-2015
Abstract: Painful diabetic neuropathy (PDN) is a type of peripheral neuropathic pain that is often intractable. Elevated nitric oxide (NO) from neuronal and non-neuronal sources in the somatosensory system is implicated in the pathobiology of peripheral neuropathic pain. However, in diabetes, nitrergic nerve degeneration to deplete NO bioactivity appears causal in the pathogenesis of irreversible autonomic neuropathy, another long term complication of diabetes. Hence, this study hypothesized that progressive NO depletion may underpin the pathobiology of PDN and that NO donors may alleviate PDN. Diabetes was induced in rats with intravenous streptozotocin (STZ) at 70 mg/kg and confirmed if blood glucose levels (BGLs) on day 10 post-STZ were ≥15 mmol/L. Analgesic efficacy of subcutaneous (s.c.) bolus doses of the furoxan NO donor, PRG150 was assessed in the STZ-diabetic rat model of PDN at 10-, 14- and 24-weeks post-STZ relative to the sydnominine NO donor, SIN-1 and its prodrug, molsidomine. PRG150 produced dose-dependent analgesia in STZ-diabetic rats whereas SIN-1 and molsidomine evoked neuro-excitatory side-effects, but not analgesia. The 1000-fold larger doses of PRG150 needed to produce analgesia at 14- and 24-weeks (800 pmol/kg) c.f. 10-weeks (8 fmol/kg) post-STZ in rats, suggest that progressive NO depletion is also causal in PDN. Importantly, doses of PRG150 up to 10 000 fold higher than the analgesic dose did not produce hypotension in rats. The 50-fold greater release of NO by SIN-1 c.f. PRG150 in vitro, may underpin the neuro-excitatory rather than analgesic effects of SIN-1/molsidomine. PRG150 is worthy of further investigation as a potential novel analgesic for PDN.
Tissue growth controlled by geometric boundary conditions: a simple model recapitulating aspects of callus formation and bone healing
Publisher: The Royal Society
Date: 06-2015
Abstract: The shape of tissues arises from a subtle interplay between biochemical driving forces, leading to cell growth, ision and extracellular matrix formation, and the physical constraints of the surrounding environment, giving rise to mechanical signals for the cells. Despite the inherent complexity of such systems, much can still be learnt by treating tissues that constantly remodel as simple fluids. In this approach, remodelling relaxes all internal stresses except for the pressure which is counterbalanced by the surface stress. Our model is used to investigate how wettable substrates influence the stability of tissue nodules. It turns out for a growing tissue nodule in free space, the model predicts only two states: either the tissue shrinks and disappears, or it keeps growing indefinitely. However, as soon as the tissue wets a substrate, stable equilibrium configurations become possible. Furthermore, by investigating more complex substrate geometries, such as tissue growing at the end of a hollow cylinder, we see features reminiscent of healing processes in long bones, such as the existence of a critical gap size above which healing does not occur. Despite its simplicity, the model may be useful in describing various aspects related to tissue growth, including biofilm formation and cancer metastases.
Unprecedented 1,14-seco-crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer-Villiger rearrangement.
Publisher: Wiley
Date: 18-09-2014
Abstract: EBC-162 isolated from Croton insularis, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C (4). Novel oxidative degradation products, EBC-233 and EBC-300, which are the first crotofolane endoperoxides, were also isolated. Both endoperoxides were found to be stable intermediates, which are proposed to undergo an unprecedented homo-Baeyer-Villiger biosynthetic rearrangement to give a new class of 1,14-seco-crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented.
Food Allergy Readiness and Anaphylaxis Management in Early Childhood Education and Care in Western Australia
Publisher: SAGE Publications
Date: 12-2018
Abstract: WITH THE INCREASE IN prevalence of food allergy (FA) in young children, early childhood education and care (ECEC) providers are likely to have more enrolments of children who are at risk of anaphylaxis. This study examines the status of FA management in ECEC, and assesses the services’ current readiness to prevent and manage FA. A cross-sectional study comprising an online survey with multiple-choice and open-ended questions was conducted with 53 long day care services in Western Australia. Among the respondents, 83 per cent of services had at least one child enrolled with FA, 96 per cent had an FA policy, and 91 per cent required staff to undertake anaphylaxis training. A high level of self-reported confidence and skills were demonstrated however, gaps were identified in risk-minimisation knowledge, use of adrenaline (epinephrine) autoinjectors and available resources. Extensive promotion of available resources will help improve compliance with anaphylaxis guidelines.
Unmasking Inherent Chirality within the Cubane Skeleton
Publisher: Wiley
Date: 04-2021
Abstract: Cubane, a hexahedral hydrocarbon, can be converted into an asymmetric molecule with a minimum of three substituents. The resulting chiral cubane can be used as a pharmacophore or a chiral ligand. Starting from the cubane carboxamide, the 1,2,3‐substituted compound was synthesized by sequential ortho ‐metalation. The 1,3,5‐substituted compound was synthesized by combining site‐selective halogenation and halogen‐metal exchange and the resulting racemate was subjected to enantiomeric resolution by HPLC.
Synthesis of Zeolite A from Iraqi Natural Kaolin Using a Conventional Hydrothermal Synthesis Technique
Publisher: University of Kurdistan Hewler
Date: 31-12-2020
DOI: 10.25079/UKHJSE.V4N2Y2020.PP11-23
Abstract: The synthesis of zeolite materials by hydrothermal transformation of kaolin using a conventional hydrothermal method was investigated. Different analytical techniques were used to characterize the starting kaolin and produced zeolite A s les, including scanning electron microscopy (SEM), energy-dispersive spectroscopy (EDS), x-ray diffraction (XRD), x-ray fluorescence (XRF), thermogravimetric analysis (TGA), and Fourier transform infrared (FT-IR) spectroscopy. The synthetic zeolite type A was obtained after activation of kaolin and metakaolin followed by different thermal and chemical treatments. The metakaolinization phase was achieved by calcining the kaolin in air at 600°C for 3 hours, a much lower temperature than previously reported in the literature. Metakaolin was treated with 3 M sodium hydroxide solution at a ratio of 1:5 and, using stainless steel autoclaves with teflon liners, heated the mixture to 200°C in a microwave for 24 hours. The results from this synthesis route showed that zeolite A with a cubic crystal habit has been successfully synthesized.
Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process
Publisher: Elsevier BV
Date: 09-2009
Anticancer agents from the Australian tropical rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76.
Publisher: Wiley
Date: 20-10-2009
Abstract: EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8 % overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze-Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell line DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults.
The cubane paradigm in bioactive molecule discovery: further scope, limitations and the cyclooctatetraene complement
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9OB01238A
Abstract: Trials and tribulations of the cubane paradigm in biomolecule discovery highlight synthetic limitations, culminating in a continuing guide for practitioners, which includes cyclooctatetraene.
Network architecture strongly influences the fluid flow pattern through the lacunocanalicular network in human osteons
Publisher: Springer Science and Business Media LLC
Date: 28-11-2019
DOI: 10.1007/S10237-019-01250-1
Abstract: A popular hypothesis explains the mechanosensitivity of bone due to osteocytes sensing the load-induced flow of interstitial fluid squeezed through the lacunocanalicular network (LCN). However, the way in which the intricate structure of the LCN influences fluid flow through the network is largely unexplored. We therefore aimed to quantify fluid flow through real LCNs from human osteons using a combination of experimental and computational techniques. Bone s les were stained with rhodamine to image the LCN with 3D confocal microscopy. Image analysis was then performed to convert image stacks into mathematical network structures, in order to estimate the intrinsic permeability of the osteons as well as the load-induced fluid flow using hydraulic circuit theory. Fluid flow was studied in both ordinary osteons with a rather homogeneous LCN as well as a frequent subtype of osteons—so-called osteon-in-osteons—which are characterized by a ring-like zone of low network connectivity between the inner and the outer parts of these osteons. We analyzed 8 ordinary osteons and 9 osteon-in-osteons from the femur midshaft of a 57-year-old woman without any known disease. While the intrinsic permeability was 2.7 times smaller in osteon-in-osteons compared to ordinary osteons, the load-induced fluid velocity was 2.3 times higher. This increased fluid velocity in osteon-in-osteons can be explained by the longer path length, needed to cross the osteon from the cement line to the Haversian canal, including more fluid-filled lacunae and canaliculi. This explanation was corroborated by the observation that a purely structural parameter—the mean path length to the Haversian canal—is an excellent predictor for the average fluid flow velocity. We conclude that osteon-in-osteons may be particularly significant contributors to the mechanosensitivity of cortical bone, due to the higher fluid flow in this type of osteons.
Shape-preserving erosion controlled by the graded microarchitecture of shark tooth enameloid
Publisher: Springer Science and Business Media LLC
Date: 24-11-2020
DOI: 10.1038/S41467-020-19739-0
Abstract: The teeth of all vertebrates predominantly comprise the same materials, but their lifespans vary widely: in stark contrast to mammals, shark teeth are functional only for weeks, rather than decades, making lifelong durability largely irrelevant. However, their diets are erse and often mechanically demanding, and as such, their teeth should maintain a functional morphology, even in the face of extremely high and potentially damaging contact stresses. Here, we reconcile the dilemma between the need for an operative tooth geometry and the unavoidable damage inherent to feeding on hard foods, demonstrating that the tooth cusps of Port Jackson sharks, hard-shelled prey specialists, possess unusual microarchitecture that controls tooth erosion in a way that maintains functional cusp shape. The graded architecture in the enameloid provokes a location-specific damage response, combining chipping of outer enameloid and smooth wear of inner enameloid to preserve an efficient shape for grasping hard prey. Our discovery provides experimental support for the dominant theory that multi-layered tooth enameloid facilitated evolutionary ersification of shark ecologies.
A Combined DFT and NMR Investigation of the Zinc Organometallic Intermediate Proposed in the Syn-Selective Tandem Chain Extension–Aldol Reaction of β-Keto Esters
Publisher: American Chemical Society (ACS)
Date: 03-07-2012
DOI: 10.1021/JO3004925
Commercial Herbicides Can Trigger the Oxidative Inactivation of Acetohydroxyacid Synthase
Publisher: Wiley
Date: 29-02-2016
Abstract: Acetohydroxyacid synthase (AHAS) inhibitors are highly successful commercial herbicides. New kinetic data show that the binding of these compounds leads to reversible accumulative inhibition of AHAS. Crystallographic data (to a resolution of 2.17 Å) for an AHAS-herbicide complex shows that closure of the active site occurs when the herbicidal inhibitor binds, thus preventing exchange with solvent. This feature combined with new kinetic data shows that molecular oxygen promotes an accumulative inhibition leading to the conclusion that the exceptional potency of these herbicides is augmented by subversion of an inherent oxygenase side reaction. The reactive oxygen species produced by this reaction are trapped in the active site, triggering oxidation reactions that ultimately lead to the alteration of the redox state of the cofactor flavin adenine dinucleotide (FAD), a feature that accounts for the observed reversible accumulative inhibition.
Towards the Total Synthesis of Gedunin: Construction of the Fully Elaborated ABC Ring System
Publisher: Wiley
Date: 08-03-2017
Tensile forces drive a reversible fibroblast-to-myofibroblast transition during tissue growth in engineered clefts
Publisher: American Association for the Advancement of Science (AAAS)
Date: 05-01-2018
Abstract: Fibroblasts transition into myofibroblasts in a highly tensed growth front and revert back to fibroblasts as the tissue matures.
Exploiting the Anders–Gaßner variant on the Wittig reaction: new methodology for the synthesis of 3,3-dimethylacroyl enol esters
Publisher: Elsevier BV
Date: 06-2008
A concise total synthesis of (±)-cipadonoid B from synthetic azedaralide
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0CC04698A
Abstract: The tetranortriterpene cipadonoid B was efficiently constructed from synthetic azedaralide in a one-pot cascade, via the underutilised ketal-Claisen rearrangement.
The Role of Titanium Surface Nanostructuring on Preosteoblast Morphology, Adhesion, and Migration
Publisher: Wiley
Date: 30-03-2017
Abstract: Surface structuring of titanium-based implants is known to modulate the behavior of adherent cells, but the influence of different nanotopographies is poorly understood. The aim is to investigate preosteoblast proliferation, adhesion, morphology, and migration on surfaces with similar surface chemistry but distinct nanotopographical features. Sonochemical treatment and anodic oxidation are employed to fabricate disordered, mesoporous titania (TMS) and ordered titania nanotubular (TNT) topographies on titanium, respectively. Morphological evaluation reveals that cells are polygonal and well-spread on TMS, but display an elongated, fibroblast-like morphology on TNT surfaces, while they are much flatter on glass. Both nanostructured surfaces impair cell adhesion, but TMS is more favorable for cell growth due to its support of cell attachment and spreading in contrast to TNT. A quantitative wound healing assay in combination with live-cell imaging reveals that cell migration on TMS surfaces has a more collective character than on other surfaces, probably due to a closer proximity between neighboring migrating cells on TMS. The results indicate distinctly different cell adhesion and migration on ordered and disordered titania nanotopographies, providing important information that can be used in optimizing titanium-based scaffold design to foster bone tissue growth and repair while allowing for the encapsulation of drugs into porous titania layer.
Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations
Publisher: Wiley
Date: 29-01-2019
Abstract: The scope and limitations of Eaton's rhodium(I)-catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane-alcohols to undergo one-pot tandem Ley-Griffith Wittig reactions in the absence of a transition metal catalyst.
All but diamonds Biological materials are not forever
Publisher: Elsevier BV
Date: 02-2013
Reassignment of Improbable Natural Products Identified through Chemical Principle Screening
Publisher: Wiley
Date: 13-07-2022
Abstract: Natural products continue to be reported at an astonishing rate from a wide range of multidisciplinary research activities in the pursuit of understanding the chemistry of bio ersity. However, the elucidation of chemical structure in the modern era is heavily reliant on the analysis and interpretation of multiple spectroscopic outputs, and in most cases this activity is by no means trivial. Structural errors continue to be described given the inherent complexity of natural products. Computer‐Assisted Structure Elucidation (CASE) continues to provide improved resolving power in this regard, but for enhanced accuracy quantum chemical spectrum prediction methodology is paramount. Reported herein are a range of counterfactual natural products, identified through chemical principal screening, which have been reassigned using a combination of chemical intuition, chemical synthesis, CASE and DU8+ spectrum prediction.
Neighboring group stabilization by σ-holes
Publisher: Springer Science and Business Media LLC
Date: 15-08-2009
DOI: 10.1007/S00894-009-0567-1
Abstract: We have used density-functional theory to investigate the neighboring-group stabilization of iodine, arsenic, and phosphorus-centered oxyanion moieties in species such as deprotonated 2-iodoxybenzoic acid (IBX) and its analogs. The magnitudes of different stabilizing effects and further candidates for analogous stabilization are analyzed.
Chiral Auxiliary-Directed Site-Selective Deprotonation of the Cubane Skeleton
Publisher: American Chemical Society (ACS)
Date: 03-01-2023
Two-step regio- and stereoselective synthesis of cis-vinylstannanes
Publisher: American Chemical Society (ACS)
Date: 14-08-2008
DOI: 10.1021/OL801251M
Abstract: Herein we describe a novel stereoselective synthesis of cis-vinylstannanes employing the widely established Li/Te exchange pathway. In contrast to previously reported methods of cis-selective hydrostannation (i.e., ZrCl4), this method demonstrates compatibility toward oxygenated substrates.
Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility
Publisher: Wiley
Date: 27-06-2019
Abstract: Common oxidants used in chemical synthesis, including newly developed perruthenates, were evaluated in the context of understanding (and better appreciating) the sensitiveness and associated potential hazards of these reagents. Analysis using sealed cell differential scanning calorimetry (scDSC) facilitated Yoshida correlations, which were compared to impact sensitiveness and electrostatic discharge experiments (ESD), that enabled sensitiveness ranking. Methyltriphenylphoshonium perruthenate (MTP3, 8), isoamyltriphenylphosphonium perruthenate (ATP3, 7) and tetraphenylphosphonium perruthenate (TP3, 9) were found to be the most sensitive followed by 2-iodoxybenzoic acid (IBX, 2) and benzoyl peroxide (BPO, 10), whereas the most benign were observed to be Oxone (12), manganese dioxide (MnO
Design, synthesis and evaluation of alpha lipoic acid derivatives to treat multiple sclerosis-associated central neuropathic pain
Publisher: Elsevier BV
Date: 09-2022
DOI: 10.1016/J.BMC.2022.116889
Abstract: Multiple sclerosis-associated central neuropathic pain (MS-CNP) is difficult to alleviate with clinically used pain-killers and so there is a large unmet medical need for novel treatments for alleviating MS-CNP. Although (R)-alpha lipoic acid (ALA) evoked significant pain relief efficacy in a mouse model of multiple sclerosis-associated central neuropathic pain (MS-CNP), this dietary supplement has poor oral bioavailability due to low gastric stability. Eight ester prodrugs of the R enantiomer of ALA [(R)-ALA] were designed encompassing a range of biocompatible hydrophobic and hydrophilic features and synthesized in an effort to identify a prodrug candidate that was stable at gastric and upper gastrointestinal tract (GIT) pH, and that could be released (hydrolyzed by esterases) in the blood to (R)-ALA immediately after absorption into the portal vein (i.e., highly desirable features for pain relief development). These biocompatible hydrophobic and hydrophilic (R)-ALA pro-dugs underwent comprehensive preliminary screening to reveal PD-ALA4 HCl salt (10) as a promising candidate and PD-ALA 7 (8) could be a viable substitute, utilizing enzyme-free gastric and intestinal stability assessments, LogP evaluations, in vitro plasma stability and caco-2 cell monolayer permeability.
Synthetic Tigliane Intermediates Engage Thiols to Induce Potent Cell Line Selective Anti‐Cancer Activity
Publisher: Wiley
Date: 29-09-2020
Abstract: The tigliane ring system, which encompasses iconic members such as phorbol and TPA, is widely renowned due to numerous observations of displaying potent biological activity, and subsequent use as mainstream biochemical tools. Traditionally, naturally occurring phorboids are regarded as tumor promotors through PKC activation, although in recent times more highly oxidized natural derivatives have been identified as anti‐tumor agents. In the view that only limited synthetic investigations toward skeletal stereochemical modification have been undertaken, non‐natural systems could be useful for a better understanding of the tigliane pharmacophore via interrogation of cellular sensitivity. In this context the concise construction of a number of highly functionalized non‐natural D‐ring inverted phorbol esters were synthesized, via a rhodium‐catalyzed [4+3] cycloaddition, and biologically evaluated using a range of cancer cell lines. The biological results highlight the notion that subtle changes in structure have dramatic effects on potency. Furthermore, although the non‐natural derivatives did not outcompete the natural systems in the PKC‐activation sensitive MCF7 cancer cell line, they outperformed in other cancer cell lines (MM96L and CAL27). This observation strongly suggested an alternate mode of action not involving activation of PKC, but instead involves thiol addition as indicated by glutathione addition and NF‐κB reporter activity.
Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case
Publisher: Wiley
Date: 17-03-2011
Enantioselective total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C1CC15995J
Abstract: The first total synthesis of vibsane-type diterpenoids neovibsanin G and 14-epi-neovibsanin G has been achieved. Key to this endeavour was a late stage EtAlCl(2) mediated skeletal rich cascade leading to the bicyclo[3.3.1]nonane core in one step.
Tandem Oxidation-Dehydrogenation of (Hetero)Arylated Primary Alcohols via Perruthenate Catalysis
Publisher: CSIRO Publishing
Date: 30-08-2021
DOI: 10.1071/CH21137
Abstract: Tandem oxidative-dehydrogenation of primary alcohols to give α,β-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO·PF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO·PF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.
Inhibition of adventitious rooting inBackhousia citriodoraF. Muell. cuttings correlate with the concentration of essential oil
Publisher: Informa UK Limited
Date: 2002
The Story Behind the Total Synthesis of Vibsanin E and 5-epi-Vibsanin E
Publisher: Elsevier
Date: 2012
The clerodane ring system: investigating the viability of a direct Diels–Alder approach
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1OB05422H
Abstract: A direct synthetic approach to the spiro-γ-lactone clerodane ring system has been investigated. This work builds on that of Jung and highlights the inherent difficulties associated with the otherwise obvious Diels-Alder approach.
Kinetic Studies of Heavy Metal Removal from Industrial Wastewater by Using Natural Zeolite
Publisher: University of Kurdistan Hewler
Date: 30-06-2021
DOI: 10.25079/UKHJSE.V5N1Y2021.PP18-25
Abstract: The present work involves the study of the removal of Cu2+, Fe3+, Pb2+ and Zn2+ from synthetic metal solutions using natural zeolite. Laboratory experiments were used to investigate the efficiency of adsorbents in the uptake of heavy metals from industrial wastewater. The kinetic study was used to identify the effect of parameters that affect the rate of adsorption and evaluated their impact on the efficiency of the zeolite in the removal of heavy metals from industrial wastewater. Natural zeolite (clinoptilolite) as adsorbent contacted with multi-component synthetic solutions containing Cu2+, Fe3+, Pb2+ and Zn2+ ions without any pre-modifications and every hour 15 ml of the s les were filtered and taken for metal ion concentration analysis using the ICP-OES. The pH values were monitored and adjusted regularly. The results showed that the capacity of the adsorbents for the removal of heavy metals increased with a greater mass of absorbent, increased initial solution pH, increased agitation speed and higher solution concentration.
Key achievements in the total synthesis of vibsane-type diterpenoids
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2NP00067A
Abstract: Vibsanins are rare, structurally dense diterpenes, which occur exclusively in the Viburnum species. Despite the first reported isolation thirty one years ago, this natural product family has only attracted synthetic attention within the past decade. The aim of this article is to highlight the key accomplishments in the total synthesis of these unique natural products.
Heteroatom-Interchanged Isomers of Lissoclinamide 5: Copper(II) Complexation, Halide Binding, and Biological Activity
Publisher: Wiley
Date: 25-03-2018
Direct Observation of an Oxepin from a Bacterial Cytochrome P450-Catalyzed Oxidation.
Publisher: Wiley
Date: 16-02-2016
Abstract: The cytochromes P450 are hemoproteins that catalyze a range of oxidative C-H functionalization reactions, including aliphatic and aromatic hydroxylation. These transformations are important in a range of biological contexts, including biosynthesis and xenobiotic biodegradation. Much work has been carried out on the mechanism of aliphatic hydroxylation, implicating hydrogen atom abstraction, but aromatic hydroxylation is postulated to proceed differently. One mechanism invokes as the key intermediate an arene oxide (and/or its oxepin tautomer). Conclusive isolation of this intermediate has remained elusive and, currently, direct formation of phenols from a Meisenheimer intermediate is believed to be favored. We report here the identification of a P450 [P450cam (CYP101A1) and P450cin (CYP176A1)]-generated arene oxide as a product of in vitro oxidation of tert-butylbenzene. Computations (CBS-QB3) predict that the arene oxide and oxepin have similar stabilities to other arene oxides/oxepins implicated (but not detected) in P450-mediated transformations, suggesting that arene oxides can be unstable terminal products of P450-catalyzed aromatic oxidation that can explain the origin of some observed metabolites.
Stereocontrolled Synthesis of the cis-Hydroxydecalin System: Towards Biologically Active 19-nor-Clerodanes
Publisher: Wiley
Date: 26-01-2012
EBC-219: A New Diterpene Skeleton, Crotinsulidane, from the Australian Rainforest Containing a Bridgehead Double Bond
Publisher: Wiley
Date: 05-05-2014
Genome-Guided Analysis of Seven Weed Species Reveals Conserved Sequence and Structural Features of Key Gene Targets for Herbicide Development
Publisher: Frontiers Media SA
Date: 29-06-2022
Abstract: Herbicides are commonly deployed as the front-line treatment to control infestations of weeds in native ecosystems and among crop plants in agriculture. However, the prevalence of herbicide resistance in many species is a major global challenge. The specificity and effectiveness of herbicides acting on erse weed species are tightly linked to targeted proteins. The conservation and variance at these sites among different weed species remain largely unexplored. Using novel genome data in a genome-guided approach, 12 common herbicide-target genes and their coded proteins were identified from seven species of Weeds of National Significance in Australia: Alternanthera philoxeroides (alligator weed), Lycium ferocissimum (African boxthorn), Senecio madagascariensis (fireweed), Lantana camara (lantana), Parthenium hysterophorus (parthenium), Cryptostegia grandiflora (rubber vine), and Eichhornia crassipes (water hyacinth). Gene and protein sequences targeted by the acetolactate synthase (ALS) inhibitors and glyphosate were recovered. Compared to structurally resolved homologous proteins as reference, high sequence conservation was observed at the herbicide-target sites in the ALS (target for ALS inhibitors), and in 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase (target for glyphosate). Although the sequences are largely conserved in the seven phylogenetically erse species, mutations observed in the ALS proteins of fireweed and parthenium suggest resistance of these weeds to ALS-inhibiting and other herbicides. These protein sites remain as attractive targets for the development of novel inhibitors and herbicides. This notion is reinforced by the results from the phylogenetic analysis of the 12 proteins, which reveal a largely consistent vertical inheritance in their evolutionary histories. These results demonstrate the utility of high-throughput genome sequencing to rapidly identify and characterize gene targets by computational methods, bypassing the experimental characterization of in idual genes. Data generated from this study provide a useful reference for future investigations in herbicide discovery and development.
Corrigendum to: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere (Angewandte Chemie International Edition, (2016), 55, 11, (3580-3585), 10.1002/anie.201510675)
Publisher: Wiley
Date: 05-07-2018
Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation
Publisher: Wiley
Date: 24-04-2019
Photochemical generation of the 2-azabicyclo[4.2.0]octa-4,7-diene skeleton
Publisher: CSIRO Publishing
Date: 31-08-2022
DOI: 10.1071/CH22139
Abstract: A 2-azabicyclo[4.2.0]octa-4,7-diene derivative was unexpectedly isolated from the photochemical irradiation of 2-vinyl-1,2-dihydropyridine. A cascading 6π–8π–4π electrocyclic rearrangement has been proposed as a possible mechanistic pathway.
Humulene Diepoxides from the Australian Arid Zone Herb Dysphania: Assignment of Aged Hops Constituents
Publisher: Wiley
Date: 21-01-2020
Abstract: Dysphania is an abundant genus of plants, many of which are endemic to the Australian continent, occurring primarily in arid and temperate zones. Despite their prevalence, very few investigations into the phytochemistry of native Dysphania have been undertaken. Described herein, is the isolation and elucidation of two enantiomeric diastereomers of humulene diepoxide C from D. kalpari and D. rhadinostachya , of which unassigned diastereomers of humulene diepoxide C have been previously reported as components in beer brewed from aged hops. In addition, two (+)‐humulene diepoxiols (humulene diepoxiol C‐I and C‐II) were isolated from D. rhadinostachya . Analysis of Chinook hops oil confirmed the presence of both humulene diepoxide C‐I and C‐II as trace components, and in turn enabled GC‐MS peak assignment to the relative stereochemistry. Anticancer assays did not reveal any significant activity for the (+)‐humulene diepoxides. Antifungal assays showed good activity against a drug‐resistant strain of C. auris , with MIC 50 values of 8.53 and 4.91 μ m obtained for (+)‐humulene diepoxide C‐I and C‐II, respectively.
Inside Cover: Do Anti-Bredt Natural Products Exist? Olefin Strain Energy as a Predictor of Isolability (Angew. Chem. Int. Ed. 36/2015)
Publisher: Wiley
Date: 13-08-2015
Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere
Publisher: Wiley
Date: 05-02-2016
Abstract: Pharmaceutical and agrochemical discovery programs are under considerable pressure to meet increasing global demand and thus require constant innovation. Classical hydrocarbon scaffolds have long assisted in bringing new molecules to the market place, but an obvious omission is that of the Platonic solid cubane. Eaton, however, suggested that this molecule has the potential to act as a benzene bioisostere. Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agrochemicals. Two cubane analogues showed increased bioactivity compared to their benzene counterparts whereas two further analogues displayed equal bioactivity, and the fifth one demonstrated only partial efficacy. Ramifications from this study are best realized by reflecting on the number of bioactive molecules that contain a benzene ring. Substitution with the cubane scaffold where possible could revitalize these systems, and thus expedite much needed lead candidate identification.
Chromatography with silver nitrate
Publisher: Elsevier BV
Date: 2001
5th Heron Island Conference on Reactive Intermediates and Unusual Molecules
Publisher: CSIRO Publishing
Date: 2010
DOI: 10.1071/CH10389
Seco-Casbanes from the Australian Rainforest: ECD Predictions Key for Determining Remote Absolute Configuration
Publisher: Wiley
Date: 03-2016
Organocopper(ii ) complexes: new catalysts for carbon–carbon bond formation via electrochemical atom transfer radical addition (eATRA)
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2SC03418B
Abstract: Electrochemical generation of a novel organocopper( ii ) complex offers a new way to carry out atom transfer radical addition to alkenes under mild conditions with high yields and low catalyst loadings.
AN IMPROVED PREPARATION OF 4-AMINO-3-MERCAPTOBENZOIC ACID
Publisher: Informa UK Limited
Date: 10-2003
Structural Reassignment of Two Polyenol Natural Products
Publisher: Wiley
Date: 03-02-2023
Abstract: Unusual polyenols that defied chemical principles were reassigned as the nucleosides, adenosine and uridine, using a combination of chemical intuition underpinned by Computer Assisted Structure Elucidation (CASE) and DFT methods.
The 2.0 Å X-ray structure for yeast acetohydroxyacid synthase provides new insights into its cofactor and quaternary structure requirements
Publisher: Public Library of Science (PLoS)
Date: 08-02-2017
Pressurized honeycombs as soft-actuators: a theoretical study (vol 11, 20140458, 2014)
Publisher: The Royal Society
Date: 06-12-2014
N-Oxides rescue Ru(v ) in catalytic Griffith–Ley (TPAP) alcohol oxidations
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CC05440D
Abstract: Electrochemistry of tetrapropylammonium perruthenate (TPAP) reveals that an unstable Ru( v ) complex is reoxidised by amine N -oxides in catalytic Griffith–Ley alcohol oxidations.
Evaluating the Baylis-Hillman reaction of cyclic enones using surfactants in water
Publisher: Georg Thieme Verlag KG
Date: 27-10-2005
2nd International Collaborative and Cooperative Chemistry Symposium
Publisher: CSIRO Publishing
Date: 2012
DOI: 10.1071/CH12231
Chromatography with silver nitrate: part 2
Publisher: Elsevier BV
Date: 03-2016
En Route to D-Ring Inverted Phorbol Esters
Publisher: American Chemical Society (ACS)
Date: 18-10-2019
DOI: 10.1021/ACS.ORGLETT.9B03379
Abstract: Phorbol esters are long regarded as tumor promotors, due to protein kinase C (PKC) activation, but more recently higher oxidized natural derivatives have been shown to display antitumor activity. Given the synthetic difficulty, systematic non-natural systems are not readily available to further interrogate PKC binding. Herein reported is the concise construction of a considerably advanced intermediate toward D-ring inverted phorbol esters, enabled by a rhodium-catalyzed [4 + 3] cycloaddition involving a highly functionalized tetrahydrobenzofuran.
Dialkyl Carbonate Synthesis via in Situ Generated Carbonyl Dibromide on Porous Glass
Publisher: American Chemical Society (ACS)
Date: 08-2017
Enone-promoted decarboxylation of trans-4-hydroxy-l-proline in flow: a side-by-side comparison to batch
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0RE00442A
Abstract: An efficient and scalable enone-promoted method for the decarboxylation of trans -4-hydroxy-proline has been developed in flow to provide access to ( R )-pyrrolidin-3-ol hydrochloride using biomass-derived isophorone.
Saireito (TJ-114), a Japanese Traditional Herbal Medicine, Reduces 5-Fluorouracil-Induced Intestinal Mucositis in Mice by Inhibiting Cytokine-Mediated Apoptosis in Intestinal Crypt Cells
Publisher: Public Library of Science (PLoS)
Date: 07-01-2015
Cover Picture: Towards the Total Synthesis of Gedunin: Construction of the Fully Elaborated ABC Ring System (Asian J. Org. Chem. 5/2017)
Publisher: Wiley
Date: 05-2017
ChemInform Abstract: NMO·TPB: A Selectivity Variation on the Ley-Griffith TPAP Oxidation.
Publisher: Wiley
Date: 07-2015
Unearthing the Subtleties of Rhodium(II)-Catalyzed Carbenoid Cycloadditions to Furans with an N-Sulfonyl-1,2,3-triazole Probe
Publisher: American Chemical Society (ACS)
Date: 13-12-2022
Mono- and Disubstituted N,N-Dialkylcyclopropylamines from Dialkylformamides via Ligand-Exchanged Titanium–Alkene Complexes Part 79 in the series “Cyclopropyl Building Blocks for Organic Synthesis”. Fo
Publisher: Wiley
Date: 16-08-2002
DOI: 10.1002/1521-3765(20020816)8:16<3789::AID-CHEM3789>3.0.CO;2-R
Correlative imaging reveals physiochemical heterogeneity of microcalcifications in human breast carcinomas
Publisher: Elsevier BV
Date: 04-2217
Multilevel architectures in natural materials
Publisher: Elsevier BV
Date: 2013
The Chemistry of 5-Oxodihydroisoxazoles. XVI. A New Synthesis of Pyrroles, Furans, Thiophens and Their Benzo Analogues
Publisher: CSIRO Publishing
Date: 1996
DOI: 10.1071/CH9961315
Abstract: Ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate (2) was photolysed at 300 nm in the presence of phenols, enols, anilines, enamines , aryl thiols and thioenols affording enamines. Treatment of these enamines with Lewis or protic acids gives the respective benzo and five- membered ring systems.
Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources
Publisher: American Chemical Society (ACS)
Date: 07-01-2022
DOI: 10.1021/ACS.JMEDCHEM.0C01915
Abstract: Strong opioid analgesics, including morphine, are the mainstays for treating moderate to severe acute pain and alleviating chronic cancer pain. However, opioid-related adverse effects, including nausea or vomiting, sedation, respiratory depression, constipation, pruritus (itch), analgesic tolerance, and addiction and abuse liability, are problematic. In addition, the use of opioids to relieve chronic noncancer pain is controversial due to the "opioid crisis" characterized by opioid misuse or abuse and escalating unintentional death rates due to respiratory depression. Hence, considerable research internationally has been aimed at the "Holy Grail" of the opioid analgesic field, namely the discovery of novel and safer opioid analgesics with improved opioid-related adverse effects. In this Perspective, medicinal chemistry strategies are addressed, where structurally erse nonmorphinan-based opioid ligands derived from natural sources were deployed as lead molecules. The current state of play, clinical or experimental status, and novel opioid ligand discovery approaches are elaborated in the context of retaining analgesia with improved safety and reduced adverse effects, especially addiction liability.
Kinetico-Mechanistic Studies on a Reactive Organocopper(II) Complex: Cu–C Bond Homolysis versus Heterolysis
Publisher: American Chemical Society (ACS)
Date: 06-03-2023
Unprecedented photochemical induced cascading rearrangement of the 3-azabicyclo[3.3.1]nonane skeletonElectronic supplementary information (ESI) available: experimental details and characterisation dat
Publisher: Royal Society of Chemistry (RSC)
Date: 2004
DOI: 10.1039/B402200A
Abstract: Certain 3-azabicyclo[3.3.1]nonane derivatives undergo unprecedented stereospecific skeletal cleavage when subjected to light affording a novel heterotricyclic skeleton.
Toward the total synthesis of alpkinidine: synthesis of haloquinone CE ring system synthons and attempted nucleophilic bisannulation
Publisher: American Chemical Society (ACS)
Date: 06-2022
Toward the Total Synthesis of Alpkinidine: Michael Addition to Isoquinolinetrione CE Ring-System Synthons
Publisher: American Chemical Society (ACS)
Date: 06-2022
Modelling of Catechin Extraction from Red Grape Solids under Conditions That Simulate Red Wine Fermentation
Publisher: MDPI AG
Date: 19-04-2023
DOI: 10.3390/FERMENTATION9040394
Abstract: Digital control systems are well established in many industries and could find application in the wine sector. Of critical importance to red wine quality, the efficient and targeted extraction of polyphenols from red grape solids during alcoholic fermentation could be a focus for automation. Smart technologies such as model predictive control (MPC) or fuzzy logic appear ideal for application in a complex process such as wine polyphenol extraction, but require mathematical models that accurately describe the system. The aim of this study was to derive and validate a model describing the extraction of catechin (a representative polyphenol) from red grape solids under simulated fermentation conditions. The impact of ethanol, fermentable sugar, and temperature on extraction rate was determined, with factor conditions chosen to emulate those present in industry practice. A first-order approach was used to generate an extraction model based on mass conservation that incorporated temperature and sugar dependency. Coefficients of determination (R2) for all test scenarios exceeded 0.94, indicating a good fit to the experimental data. Sensitivity analysis for the extraction rate and internal cross-validation showed the model to be robust, with a small standard error in cross-validation (SECV) of 0.11 and a high residual predictive deviation (RPD) of 17.68. The model that was developed is well suited to digital technologies where low computational overheads are desirable, and industrial application scenarios are presented for future implementation of the work.
Reductive Radical Decarboxylation of Aliphatic Carboxylic Acids
Publisher: Organic Syntheses
Date: 2012
Relation between the Macroscopic Pattern of Elephant Ivory and Its Three-Dimensional Micro-Tubular Network
Publisher: Public Library of Science (PLoS)
Date: 26-01-2017
Non-competitive cyclic peptides for targeting enzyme–substrate complexes
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8SC00286J
Abstract: Tight, non-active site binding cyclic peptides are promising affinity reagents for studying proteins and their interactions.
Mechanical behavior of idealized, stingray-skeleton-inspired tiled composites as a function of geometry and material properties
Publisher: Elsevier BV
Date: 09-2017
DOI: 10.1016/J.JMBBM.2017.02.028
Abstract: Tilings are constructs of repeated shapes covering a surface, common in both manmade and natural structures, but in particular are a defining characteristic of shark and ray skeletons. In these fishes, cartilaginous skeletal elements are wrapped in a surface tessellation, comprised of polygonal mineralized tiles linked by flexible joints, an arrangement believed to provide both stiffness and flexibility. The aim of this research is to use two-dimensional analytical models to evaluate the mechanical performance of stingray skeleton-inspired tessellations, as a function of their material and structural parameters. To calculate the effective modulus of modeled composites, we sub ided tiles and their surrounding joint material into simple shapes, for which mechanical properties (i.e. effective modulus) could be estimated using a modification of traditional Rule of Mixtures equations, that either assume uniform strain (Voigt) or uniform stress (Reuss) across a loaded composite material. The properties of joints (thickness, Young's modulus) and tiles (shape, area and Young's modulus) were then altered, and the effects of these tessellation parameters on the effective modulus of whole tessellations were observed. We show that for all examined tile shapes (triangle, square and hexagon) composite stiffness increased as the width of the joints was decreased and/or the stiffness of the tiles was increased this supports hypotheses that the narrow joints and high tile to joint stiffness ratio in shark and ray cartilage optimize composite tissue stiffness. Our models also indicate that, for simple, uniaxial loading, square tessellations are least sensitive and hexagon tessellations most sensitive to changes in model parameters, indicating that hexagon tessellations are the most "tunable" to specific mechanical properties. Our models provide useful estimates for the tensile and compressive properties of 2d tiled composites under uniaxial loading. These results lay groundwork for future studies into more complex (e.g. biological) loading scenarios and three dimensional structural parameters of biological tilings, while also providing insight into the mechanical roles of tessellations in general and improving the design of bioinspired materials.
Towards the Total Synthesis of 3-Hydroxyvibsanin E
Publisher: Georg Thieme Verlag KG
Date: 23-07-2009
Cyclic Enones as Substrates in the Morita-Baylis-Hillman Reaction: Surfactant Interactions, Scope and Scalability with an Emphasis on Formaldehyde
Publisher: Wiley
Date: 05-2009
Abstract: magnified image Traditionally, cyclic enones and formalin are reactants notorious for displaying problematic behaviour (i.e., poor solubility and low yields) under Morita–Baylis–Hillman (MBH) reaction conditions. The body of research presented herein focuses on the use of surfactants in water as a solvent medium that offers a resolution to many of the issues associated with the MBH reaction. Reaction scope, scalability and small angle X‐ray scattering have been studied to assist with the understanding of the reaction mechanism and industrial application. A comparison against known literature methods for reaction scale‐up is also discussed.
Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist
Publisher: Wiley
Date: 17-08-2018
Abstract: The Ley–Griffith oxidation, which is catalyzed by tetra‐ n ‐propylammonium perruthenate (TPAP, n Pr 4 N[RuO 4 ]), is a popular method for not only controlled oxidation of primary alcohols to aldehydes, but also a host of other synthetically useful transformations. While the fundamental reaction mechanism has recently been elucidated, several key hydrogen‐bonding interactions between the reagents were implicated but not investigated. Herein the prevalence of H‐bonding between the co‐oxidant N ‐methylmorpholine N ‐oxide (NMO), the alcohol substrate, water and the perruthenate catalyst is established. These observations help to rationalize the importance of drying the reagents and lead to several practical suggestions.
Experimental and theoretical approaches for the development of 4H-Chromene derivatives as inhibitors of tyrosinase
Publisher: Informa UK Limited
Date: 16-05-2021
EBC-316, 325–327, and 345: New Pimarane Diterpenes from Croton insularis Found in the Australian Rainforest
Publisher: CSIRO Publishing
Date: 2015
DOI: 10.1071/CH14550
Abstract: Five new pimarane and related-type diterpenes (i.e. EBC-316, 325–327, and 345 (10–15)), together with two known pimaranes (EBC-221 (8) and EBC-346 (9)), were isolated from the stems of Croton insularis, found in the Australian rainforest. All pimarane diterpenes disclosed herein are suggested to be biogenetically related to the same keto-Jacobs–Reynolds intermediate 2, via ring A and C oxidation. Anticancer activities of compounds 11–13 are reported.
Naturally occurring UBIAD1 mutations differentially affect menaquinone biosynthesis and vitamin K‐dependent carboxylation
Publisher: Wiley
Date: 12-2021
DOI: 10.1111/FEBS.16291
Abstract: UbiA prenyltransferase domain‐containing protein‐1 (UBIAD1) is responsible for the biosynthesis of menaquinone‐4 (MK‐4), a cofactor for extrahepatic carboxylation of vitamin K‐dependent (VKD) proteins. Genetic variations of UBIAD1 are mainly associated with Schnyder corneal dystrophy (SCD), a disease characterized by abnormal accumulation of cholesterol in the cornea. Results from in vitro studies demonstrate that SCD‐associated UBIAD1 mutations are defective in MK‐4 biosynthesis. However, SCD patients do not exhibit typical phenotypes associated with defects of MK‐4 or VKD carboxylation. Here, we coupled UBIAD1’s biosynthetic activity of MK‐4 with VKD carboxylation in HEK293 cells that stably express a chimeric VKD reporter protein. The endogenous Ubiad1 gene in these cells was knocked out by CRISPR‐Cas9‐mediated genome editing. The effect of UBIAD1 mutations on MK‐4 biosynthesis and VKD carboxylation was evaluated in Ubiad1 ‐deficient reporter cells by determining the production of MK‐4 or by measuring the efficiency of reporter‐protein carboxylation. Our results show that the hot‐spot mutation N102S has a moderate impact on MK‐4 biosynthesis (retained ˜ 82% activity) but does not affect VKD carboxylation. However, the G186R mutation significantly affected both MK‐4 biosynthesis and VKD carboxylation. Other mutations exhibit varying degrees of effects on MK‐4 biosynthesis and VKD carboxylation. These results are consistent with in vivo results obtained from gene knock‐in mice and SCD patients. Our findings suggest that UBIAD1’s MK‐4 biosynthetic activity does not directly correlate with the phenotypes of SCD patients. The established cell‐based assays in this study provide a powerful tool for the functional studies of UBIAD1 in a cellular milieu.
Cubanes in Medicinal Chemistry
Publisher: American Chemical Society (ACS)
Date: 23-08-2018
DOI: 10.1021/ACS.JMEDCHEM.8B00888
Abstract: Cubane is a highly strained saturated hydrocarbon system that has historically been of interest in theoretical organic chemistry. More recently it has become a molecule of interest for biological applications due to its inherent stability and limited toxicity. Of greater significance is the ability to potentially functionalize cubane at each of its carbon atoms, providing complex biologically active molecules with unique spatial arrangements for probing active sites. These characteristics have led to an increased use of cubane in pharmaceutically relevant molecules. In this Perspective we describe synthetic methodology for accessing a range of functionalized cubanes and their applications in pharmaceuticals. We also provide some perspectives on challenges and future directions in the advancement of this field.
Gains and losses of coral skeletal porosity changes with ocean acidification acclimation
Publisher: Springer Science and Business Media LLC
Date: 17-07-2015
DOI: 10.1038/NCOMMS8785
Abstract: Ocean acidification is predicted to impact ecosystems reliant on calcifying organisms, potentially reducing the socioeconomic benefits these habitats provide. Here we investigate the acclimation potential of stony corals living along a pH gradient caused by a Mediterranean CO 2 vent that serves as a natural long-term experimental setting. We show that in response to reduced skeletal mineralization at lower pH, corals increase their skeletal macroporosity (features μm) in order to maintain constant linear extension rate, an important criterion for reproductive output. At the nanoscale, the coral skeleton’s structural features are not altered. However, higher skeletal porosity, and reduced bulk density and stiffness may contribute to reduce population density and increase damage susceptibility under low pH conditions. Based on these observations, the almost universally employed measure of coral biomineralization, the rate of linear extension, might not be a reliable metric for assessing coral health and resilience in a warming and acidifying ocean.
The synthesis of oxazoles by thermolysis or photolysis of 2-acylisoxazol-5-ones
Publisher: Elsevier BV
Date: 1996
Enantioselective Total Synthesis of the Mexicanolides: Khayasin, Proceranolide, and Mexicanolide
Publisher: American Chemical Society (ACS)
Date: 20-09-2012
DOI: 10.1021/JO301182F
Abstract: The enantioselective total synthesis of the limonoids khayasin, proceranolide and mexicanolide was achieved via a convergent strategy utilizing a tactic aimed at incorporating natural products as advanced intermediates. This extended biomimetically inspired approach additionally achieved the enantioselective total synthesis of the intermediates azedaralide and cipadonoid B.
Cover Feature: Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist (Eur. J. Org. Chem. 2‐3/2019)
Publisher: Wiley
Date: 27-12-2018
Direct Access to Functionalized Cyclic Enones Using Mannich, Morita-Baylis-Hillman and Elimination Reactions
Publisher: Georg Thieme Verlag KG
Date: 02-08-2006
Construction of the Cyclovibsanin Core via a Biogenetically Modeled Approach
Publisher: American Chemical Society (ACS)
Date: 14-10-2005
DOI: 10.1021/OL051897D
Abstract: [reaction: see text] Construction of the 15-O-methylcyclovibsanin B core was achieved expediently in eight linear steps utilizing a biogenetically modeled approach.
Commercial herbicides can trigger the oxidative inactivation of acetohydroxyacid synthase
Publisher: Wiley
Date: 29-02-2016
Product Class 10: Acridin-9(10H)-ones and Related Systems
Publisher: Georg Thieme Verlag
Date: 2005
Availability of extracellular matrix biopolymers and differentiation state of human mesenchymal stem cells determine tissue-like growth in vitro
Publisher: Elsevier BV
Date: 08-2015
ChemInform Abstract: N,N,N′,N′-Tetramethylenediamine Dioxide (TMEDAO2) Facilitates Atom Economical/Open Atmosphere Ley-Griffith (TPAP) Tandem Oxidation-Wittig Reactions.
Publisher: Wiley
Date: 2016
Reassignment of the Structure of Janthinolide A
Publisher: Wiley
Date: 31-10-2023
The Chemistry of 5-Oxodihydroisoxazoles. XIII. Reactions of the Imino Carbene Derived From Photolysis of Ethyl 5-Oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate
Publisher: CSIRO Publishing
Date: 1995
DOI: 10.1071/CH9950567
Abstract: Photolysis of ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate at 300 nm in acetonitrile gives a carbene which is captured efficiently by bromide, chloride, acetate and cyanate, and less efficiently by iodide, thiocyanate, cyclohexene and tetrahydrofuran. No hydrogen abstraction or reaction with double bonds was evident.
Ultrasonically Produced Porous Sponge Layer on Titanium to Guide Cell Behavior
Publisher: Wiley
Date: 15-01-2016
Penicitone: Structural Reassignment of a Proposed Natural Product Acid Chloride
Publisher: American Chemical Society (ACS)
Date: 23-10-2023
Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C–H insertion of cubane
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8OB02959H
Abstract: An enantioselective synthesis of the non-proteinogenic amino acid ( R )-2-cubylglycine and the first ex les of cubane C–H insertion are reported.
Human and mouse bones physiologically integrate in a humanized mouse model while maintaining species-specific ultrastructure
Publisher: American Association for the Advancement of Science (AAAS)
Date: 30-10-2020
Abstract: Progress has been achieved in the art of accurately mimicking human tissues and disease in a mouse.
1-Azahomocubane
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3SC00001J
Abstract: 1-Azahomocubane has been prepared 56 years after the parent hydrocarbon. Introduction of a nitrogen atom into this constrained polycyclic environment resulted in minimal changes to the framework geometry, with s-character of the nitrogen lone pair increasing due to strain.
High Resolution Crystal Structures of the Acetohydroxyacid Synthase-Pyruvate Complex Provide New Insights into Its Catalytic Mechanism
Publisher: Wiley
Date: 21-12-2017
Cubane and Cyclooctatetraene Pirfenidones – Synthesis and Biological Evaluation
Publisher: Wiley
Date: 21-07-2023
Abstract: Pirfenidone, an oral anti‐fibrotic and anti‐inflammatory medication used for the treatment of idiopathic pulmonary fibrosis (IPF), has been proposed to treat post‐COVID pneumonia pulmonary fibrosis (PF). However, pirfenidone displays side effects which include hepatotoxicity and anorexia. Cubane and cyclooctatetraene (COT) derivatives of pirfenidone were prepared as bioisostere/biomotif replacements of the phenyl ring to explore potential changes in activity. The key intermediate, aminocubane, enabled the synthesis of both the cubane and cyclooctatetraene (COT) derived pirfenidone analogues in 6 steps. The COT derivative was observed to display similar activity and cytotoxicity with pirfenidone in an anti‐virus and ACE2 inhibition assay, although limited effect was observed from pirfenidone and the analogues described herein.
Thermal and Sensitiveness Determination of Cubanes: Towards Cubane‐Based Fuels for Infrared Countermeasures
Publisher: Wiley
Date: 24-05-2019
Abstract: As infrared seeking technology evolves, threats are better able to distinguish defensive infrared (IR) flares from true targets. Spectrally matched flares, which generally employ carbon-based fuels, are better able to decoy some advanced missiles by more closely mimicking the IR emission of the target. Cubane is a high-energy carbon-based scaffold which may be suitable for use as a fuel in spectrally matched flares. The enthalpy of formation and strain energy of a series of cubanes was predicted in silico, and their thermal and impact stability examined. All were found to undergo highly exothermic decomposition in sealed cell differential scanning calorimetry, and two cubanes subsequently underwent quantitative sensitiveness testing. Despite their F of I values being in the secondary explosive range, cubane-1,4-dicarboxylic acid (F of I=70) and 4-carbamoylcubane-1-carboxylic acid (F of I=90) were identified as potentially useful fuels for pyrotechnic infrared countermeasure flare formulations.
3D osteocyte lacunar morphometry of human bone biopsies with high resolution microCT: from monoclonal gammopathy to newly diagnosed multiple myeloma
Publisher: Cold Spring Harbor Laboratory
Date: 13-07-2023
DOI: 10.1101/2023.07.12.548656
Abstract: Osteocytes are bone-embedded cells connected via canaliculi and they regulate the bone resorption/formation balance. Osteocyte function is altered in skeletal disorders including cancer. Multiple myeloma (MM) is a hematological malignancy, whereby plasma cells disrupt the bone homeostasis and induce excessive resorption of the mineralized extracellular matrix (ECM), as evidenced by clinical computed tomography (CT). However, morphometric analyses of the mineralized ECM and bone microporosity are not yet performed in patients with MM, nor in the precursor conditions of monoclonal gammopathy of undetermined significance (MGUS) and smoldering MM (SMM). Here, we characterize changes in 3D osteocyte lacunar morphology in bone biopsy s les obtained from patients with MGUS, SMM and newly diagnosed MM, using high resolution microCT. In the small lacunae 20-900 μm 3 range, we found a trend for lower lacunar density and increasing 50% cutoff of the lacunar volume cumulative distribution for diseased s les. In the larger lacunae 900-3000 μm 3 range, we found significantly higher lacunar density and microporosity in the MM group compared to the MGUS/SMM group. Regarding the shape distribution, the MGUS/SMM group showed a trend for flatter, more elongated and anisotropic osteocyte lacunae compared to the control group, though the differences were not statistically significant. Altogether, our findings suggest that osteocytes in human MM bone disease undergo changes in their lacunae morphology, which could be an indicator for impaired bone quality. Future studies are needed to show whether these are consistent within comparable anatomical sites and could serve as a diagnostic or prognostic marker.
Total Synthesis of (±)-5,14-bis-epi-Spirovibsanin A
Publisher: American Chemical Society (ACS)
Date: 02-02-2008
DOI: 10.1021/OL702827X
Abstract: The total synthesis of (+/-)-5,14-bis-epi-spirovibsanin A was achieved in 18 steps. Physical data obtained from (+/-)-5,14-bis-epi-spirovibsanin A lends strong support to the proposed connectivity and relative stereochemistry of spirovibsanin A.
The synthesis and X-ray crystal structure of 9-carboxyhexahydro-7-methoxy-4a,7-ethano-benzopyran-5-en-1-one
Publisher: SAGE Publications
Date: 12-2003
Basimarols A, B, and C, Highly Oxygenated Pimarane Diterpenoids from Basilicum polystachyon
Publisher: American Chemical Society (ACS)
Date: 25-09-2019
DOI: 10.1021/ACS.JNATPROD.9B00522
Abstract: The highly oxygenated pimarane diterpenoids basimarols A, B, and C (
Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere
Publisher: Wiley
Date: 05-02-2016
Total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G: Towards the synthesis of 15-O-methylneovibsanin F and 14-epi-15-O-methylneovibsanin F
Publisher: Wiley
Date: 16-02-2012
Catalysts Containing the Adamantane Scaffold
Publisher: Wiley
Date: 18-02-2016
Nonstabilised azomethine ylids from n-oxides: Unravelling the deprotonation of n-methylmorpholine n-oxide
Publisher: CSIRO Publishing
Date: 2014
DOI: 10.1071/CH14217
Abstract: Nonstabilised azomethine ylids (NAYs) are useful 1,3-dipoles, but their synthetic applications are restricted by the high temperatures often needed for their generation, and by an incomplete understanding of the effect of heteroatoms in cyclic systems. We have examined the behaviour of N-methylmorpholine N-oxide (NMO) as a NAY precursor in the Roussi reaction (low-temperature reaction of an N-oxide with strong base). The choice of base is critical to achieving cycloadduct formation. We report synthetic and computational (density functional theory) investigations of the products obtained with different bases and their mechanisms of formation.
The chemistry of 5-oxodihydroisoxazoles. Part 19.1 The synthesis and photolysis of N-thioacylisoxazol-5(2H)-ones
Publisher: Royal Society of Chemistry (RSC)
Date: 1997
DOI: 10.1039/A700646B
The Chemistry of 5-Oxodihydroisoxazoles. XII. Trapping of Derived Ketenimines With Lithium Amides and Alkyllithiums
Publisher: CSIRO Publishing
Date: 1995
DOI: 10.1071/CH9950055
Abstract: Isoxazolones unsubstituted at C3 react with lithium amides or alkyllithiums to give ketenimines . The presence of an ethoxycarbonyl group at C4 allows capture of this species by addition of a second equivalent of the lithiated species to give enolates which can be alkylated in situ. The presence of a phenyl group at C4 gives a ketenimine which reacts intramolecularly in the presence of lithium amides, whereas alkyllithiums undergo addition in synthetically useful processes.
Unexpected titanium shifts during cyclopropanation of N,N-dibenzylformamide with ligand-exchanged titanium-alkadiene complexes
Publisher: Elsevier BV
Date: 10-1998
Rapid Access to in Situ Generated (R)- and (S)-2-Furyloxirane and Associated Regioselective Nucleophilic Ring-Opening Studies
Publisher: Georg Thieme Verlag KG
Date: 06-2007
Gaining Synthetic Appreciation for the Gedunin ABC Ring System
Publisher: Wiley
Date: 02-2017
Abstract: Gedunin, first isolated in 1960, displays a remarkable range of biological activity, but has yet to receive dedicated synthetic attention from a ground up construction perspective. Presented herein is a successfully executed approach to the fully functionalized ABC ring system of this challengingly complex natural product.
Hydro-actuation of ice plant seed capsules powered by water uptake
Publisher: Thomas Telford Ltd.
Date: 09-2014
DOI: 10.1680/BBN.14.00016
Abstract: Unlike well-known plant hydro-actuation systems that respond to changes in relative humidity (RH) (e.g. wheat awns), ice plant seed capsules undergo a reversible origami-like unfolding and release their seeds only in response to exposure to liquid water. The engine for ice plant actuation was found to be the water uptake and swelling of a highly swellable cellulosic inner layer (CIL) inside the cell lumen of a hygroscopic tissue responsible for the unfolding movement. CIL was found to have an open structure with porous lamellae filling the gap between denser cellulosic mats. Thermogravimetric analysis of water–CIL interaction showed that the initial enthalpy-driven adsorption of water can only account for increasing the moisture content up to about 0·4 mg/mg, which is not sufficient to initiate the actuation. By applying a combined chemo-mechanical model, we could show that the entropic gain of the system through further water uptake (40–350 wt%) is sufficient to accomplish a full opening of the seed capsules through a sophisticated design at various hierarchical levels of the system. The principles behind this actuation mechanism may inspire the development of hydro-responsive devices that, although being highly hydrophilic, only respond to liquid water and not to changes in RH.
Stable isotope dilution assay (SIDA) and HS-SPME-GCMS quantification of key aroma volatiles for fruit and sap of Australian mango cultivars
Publisher: Elsevier BV
Date: 04-2017
DOI: 10.1016/J.FOODCHEM.2016.11.130
Abstract: Reported herein is a high throughput method to quantify in a single analysis the key volatiles that contribute to the aroma of commercially significant mango cultivars grown in Australia. The method constitutes stable isotope dilution analysis (SIDA) in conjunction with headspace (HS) solid-phase microextraction (SPME) coupled with gas-chromatography mass spectrometry (GCMS). Deuterium labelled analogues of the target analytes were either purchased commercially or synthesised for use as internal standards. Seven volatiles, hexanal, 3-carene, α-terpinene, p-cymene, limonene, α-terpinolene and ethyl octanoate, were targeted. The resulting calibration functions had determination coefficients (R
Azedaralide: total synthesis, relative and absolute stereochemical assignment
Publisher: Elsevier BV
Date: 07-2006
7-Step total synthesis of (+)-EBC-329: Photoisomerisation reveals new seco-casbane family member
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7OB01400G
Abstract: The first seco -casbane, EBC-329, isolated from the Australian rainforest, was synthesised from (+)-2-carene in seven steps.
1-Ethynyl-2-isopropoxy-3-methoxybenzene
Publisher: International Union of Crystallography (IUCr)
Date: 31-03-2003
A Mechanistic Investigation into the Zinc Carbenoid-Mediated Homologation Reaction by DFT Methods: Is a Classical Donor−Acceptor Cyclopropane Intermediate Involved?
Publisher: American Chemical Society (ACS)
Date: 29-09-2010
DOI: 10.1021/JO101590T
Synthesis of Phenanthridine Derivatives via Photolysis
Publisher: American Chemical Society (ACS)
Date: 07-10-2011
DOI: 10.1021/JO201542X
Abstract: An improved photochemical method for producing the prolifically bioactive phenanthridine system is reported. A wide variety of derivatives were obtained in two steps in yields ranging from 31 to 95%.
Electrocatalytic Atom Transfer Radical Addition with Turbocharged Organocopper(II) Complexes
Publisher: American Chemical Society (ACS)
Date: 15-09-2023
Online Learners’ Reading Ability Detection Based on Eye-Tracking Sensors
Publisher: MDPI AG
Date: 10-09-2016
DOI: 10.3390/S16091457
Thermodynamic evaluation of chemical looping based nitric oxide and hydrogen production
Publisher: Elsevier BV
Date: 04-2018
Chemistry of 5-oxodihydroisoxazoles. Part 17.1 Acylation of 5-oxodihydroisoxazoles
Publisher: Royal Society of Chemistry (RSC)
Date: 1997
DOI: 10.1039/A700133I
Additions and corrections published in 2012
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CC90426H
EBC‐342: A Novel Tetrahydrofuran Moiety Containing Casbane from the Australian Rainforest
Publisher: Wiley
Date: 10-02-2020
Abstract: The Australian rainforest plant, Croton insularis , has provided a further casbane diterpene family member in the form of EBC‐342, which contains a novel tetrahydrofuran ring. A combination of DP4 and TD‐DFT CD methods were required to confirm both structure and absolute stereochemistry.
Nonclassical Phenyl Bioisosteres as Effective Replacements in a Series of Novel Open-Source Antimalarials
Publisher: American Chemical Society (ACS)
Date: 17-07-2020
Frontispiece: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere
Publisher: Wiley
Date: 29-02-2016
The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C7NP00064B
Abstract: With contributions from the global natural product (NP) research community, and continuing the Raw Data Initiative, this review collects a comprehensive demonstration of the immense scientific value of disseminating raw nuclear magnetic resonance (NMR) data, independently of, and in parallel with, classical publishing outlets.
Front Cover Picture: Catalysts Containing the Adamantane Scaffold (Adv. Synth. Catal. 5/2016)
Publisher: Wiley
Date: 16-02-2016
The (±)-6-Aza[1.0]triblattane Skeleton: Contraction beyond the Wilder–Culberson Ring System
Publisher: American Chemical Society (ACS)
Date: 19-01-2022
DOI: 10.1021/ACS.ORGLETT.1C04240
Abstract: Synthesis of the 6-aza[1.0]triblattane skeleton and the unexpected construction of the 7-azatetracyclo[4.2.1.0
Multitargeted Opioid Ligand Discovery as a Strategy to Retain Analgesia and Reduce Opioid-Related Adverse Effects
Publisher: American Chemical Society (ACS)
Date: 03-2023
Asymmetric Sequential Cu‐Catalyzed 1,6/1,4‐Conjugate Additions of Hard Nucleophiles to Cyclic Dienones: Determination of Absolute Configurations and Origins of Enantioselectivity
Publisher: Wiley
Date: 16-05-2017
Abstract: The first stereocontrolled Cu-catalyzed sequential 1,6/1,4-asymmetric conjugate addition (ACA) of C-metalated hard nucleophiles to cyclic dienones is reported. The use of DiPPAM (diphenylphosphinoazomethinylate) followed by a phosphoramidite as the stereoinducing ligands facilitated both high ee values for the 1,6-ACA and high de values for the 1,4-ACA reaction components, which thus gave enantioenriched 1,3-dialkylated moieties. The absolute configurations were determined by using vibrational circular dichroism (VCD) and optical rotatory dispersion (ORD) spectroscopy, in combination with DFT calculations and X-ray analysis. Interestingly, DFT calculations for the mechanism of enantioselective 1,6-addition by using an unprecedented Cu-Zn bimetallic catalytic system confirmed this attribution. Lastly, exploring intramolecular cyclization avenues for enantioenriched 1,3-dialkylated products provided access to the challenging drimane skeleton.
Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation
Publisher: Wiley
Date: 24-04-2019
Abstract: Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen-substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.
Intrafibrillar plasticity through mineral/collagen sliding is the dominant mechanism for the extreme toughness of antler bone
Publisher: Elsevier BV
Date: 12-2013
Inhibition of tyrosinase by 4 H ‐chromene analogs: Synthesis, kinetic studies, and computational analysis
Publisher: Wiley
Date: 12-06-2017
DOI: 10.1111/CBDD.13001
Abstract: Inhibition of mushroom tyrosinase was observed with synthetic dihydropyrano[3,2-b]chromenediones. Among them, DHPC04 displayed the most potent tyrosinase inhibitory activity with a K
o-Iodoxybenzoic Acid (IBX): pKa and Proton-Affinity Analysis
Publisher: Wiley
Date: 28-04-2006
Photochemical Synthesis of Phenanthridines: Exploring Fluoro and Protected Catechol Substitution
Publisher: Wiley
Date: 10-05-2013
Warming Accelerates Carbohydrate Consumption in the Diapausing Overwintering Peach Fruit Moth Carposina sasakii (Lepidoptera: Carposinidae)
Publisher: Oxford University Press (OUP)
Date: 17-07-2016
DOI: 10.1093/EE/NVW079
Abstract: Climate warming provides a challenge for small insects persisting in cold seasons through diapause because they fail to accumulate and maintain adequate reserves to complete this stage successfully. One way of understanding this challenge is to follow physiological changes in these insects under higher temperatures, including the consumption and allocation of energy reserves during and after diapause. We simulated autumn and spring warming conditions to study carbohydrate consumption dynamics during diapause-post-diapause periods by monitoring shifts in carbohydrate levels in a facultative diapause species, the peach fruit moth Carposina sasakii Matsumura (Lepidoptera: Carposinidae). We found carbohydrates were rapidly consumed in the post-diapause phase, which might lead to a trade-off in the allocation of energy reserves between diapause maintenance and post-diapause development. This suggests that temperature increases in autumn and spring may alter diapause maintenance and post-diapause development through changing carbohydrate levels.
Experimental determination of the gas phase proton affinities of the conjugate base anions of 2-iodoxybenzoic acid (IBX) and 2-iodosobenzoic acid (IBA)
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B803452D
Abstract: The gas phase anion proton affinities of the periodinane anions IBX- and IBA- were examined using mass spectrometry-based experiments, and estimated as 1300 +/- 25 and 1390 +/- 10 kJ mol(-1), respectively. The experimental results were supported by theoretical calculations, which yielded proton affinities of 1336 and 1392 kJ mol(-1) for IBX- and IBA- respectively, at the B3LYP/aug-cc-PVDZ level of theory.
The Anti-Bredt Red Flag! Reassignment of Neoveratrenone
Publisher: Wiley
Date: 14-10-2013
Contemplating 1,2,4-thiadiazole-inspired cyclic peptide mimics: a computational investigation
Publisher: CSIRO Publishing
Date: 2019
DOI: 10.1071/CH19248
Abstract: Marine derived cyclic peptides have inspired chemists for decades as the cavitand architecture can be compared with macrocyclic ligands, and hence easily conceived as mediators of metal-ion transport. Lissoclinamide 5 and ascidiacyclamide are two such cyclic peptides that have received much attention both for their metal ion complexation properties and biological activity the metal ion binding properties of mimics of these two systems have been reported. Reported herein is a computational study aimed at evaluating the stability, and potential for copper(ii) ion binding by lissoclinamide 5 mimics that substitute the naturally occurring 4-carboxy-1,3-thiazole units for novel valine- and phenylalanine-derived 1,2,4-thiadiazole units. Our results suggest that one lissoclinamide 5 mimic, 1,2,4-thiadiazole (TDA)-lissoclinamide 9, may be capable of forming a complex with one CuII ion, [Cu(9-H)(H2O)]+. A complex with two CuII ions, [Cu2(9-H)(μ-OH)]2+, was also considered. These results set the stage for synthetic and experimental metal binding studies.
Chemistry of 5-oxodihydroisoxazoles. Part 18.1 Synthesis of oxazoles by the photolysis and pyrolysis of 2-acyl-5-oxo-2,5-dihydroisoxazoles
Publisher: Royal Society of Chemistry (RSC)
Date: 1997
DOI: 10.1039/A700134G
Method in the Madness - Methodology from Total Synthesis
Publisher: Georg Thieme Verlag KG
Date: 29-05-2012
On shape forming by contractile filaments in the surface of growing tissues
Publisher: Oxford University Press (OUP)
Date: 12-12-2023
DOI: 10.1093/PNASNEXUS/PGAC292
Abstract: Growing tissues are highly dynamic, and flow on sufficiently long timescales due to cell proliferation, migration, and tissue remodeling. As a consequence, growing tissues can often be approximated as viscous fluids. This means that the shape of microtissues growing in vitro is governed by their surface stress state, as in fluid droplets. Recent work showed that cells in the near-surface region of fibroblastic or osteoblastic microtissues contract with highly oriented actin filaments, thus making the surface properties highly anisotropic, in contrast to what is expected for an isotropic fluid. Here, we develop a model that includes mechanical anisotropy of the surface generated by contractile fibers and we show that mechanical equilibrium requires contractile filaments to follow geodesic lines on the surface. Constant pressure in the fluid forces these contractile filaments to be along geodesics with a constant normal curvature. We then take this into account to determine equilibrium shapes of rotationally symmetric bodies subjected to anisotropic surface stress states and derive a family of surfaces of revolution. A comparison with recently published shapes of microtissues shows that this theory accurately predicts both the surface shape and the direction of the actin filaments on the surface.
Rearrangement-Free Hydroxylation of Methylcubanes by a Cytochrome P450: The Case for Dynamical Coupling of C–H Abstraction and Rebound
Publisher: American Chemical Society (ACS)
Date: 19-11-2019
DOI: 10.1021/JACS.9B08064
Abstract: The highly strained cubylmethyl radical undergoes one of the fastest radical rearrangements known (reported
seco-Pregnane Glycosides from Australian Caustic Vine (Cynanchum viminale subsp. australe)
Publisher: American Chemical Society (ACS)
Date: 16-02-2023
N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley–Griffith (TPAP) tandem oxidation-Wittig reactions
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5GC01346A
Abstract: N , N , N ′, N ′-Tetramethylethylenediamine dioxide (TMEDAO 2 ) was explored as a more atom economical co-oxidant for the Ley–Griffith oxidation of alcohols to aldehydes.
New Casbanes and the First trans-Cyclopropane seco-Casbane from the Australian Rainforest Plant Croton insularis.
Publisher: Wiley
Date: 02-01-2019
Abstract: Investigation of the Australian rainforest plant Croton insularis revealed seven new cis-, two new trans-cyclopropane casbanes, and the first trans-cyclopropane seco-casbane. The relative configuration of the cyclopropane moiety for all compounds (EBC-182, 217, 218, 220, 343, 357, 358, 361, 365, 373 EBC=EcoBiotics Compound) was assigned using
Natural products with anti-bredt and bridgehead double bonds
Publisher: Wiley
Date: 14-11-2014
Abstract: Well over a hundred years ago, Professor Julius Bredt embarked on a career pursuing and critiquing bridged bicyclic systems that contained ring strain induced by the presence of a bridgehead olefin. These endeavors founded what we now know as Bredt's rule (Bredtsche Regel). Physical, theoretical, and synthetic organic chemists have intensely studied this premise, pushing the boundaries of such systems to arrive at a better understood physical phenomenon. Mother nature has also seen fit to construct molecules containing bridgehead double bonds that encompass Bredt's rule. For the first time, this topic is reviewed in a natural product context.
Chloroform as a Hydrogen Atom Donor in Barton Reductive Decarboxylation Reactions
Publisher: American Chemical Society (ACS)
Date: 24-06-2013
DOI: 10.1021/JO400927Y
Abstract: The utility of chloroform as both a solvent and a hydrogen atom donor in Barton reductive decarboxylation of a range of carboxylic acids was recently demonstrated (Ko, E. J. et al. Org. Lett. 2011, 13, 1944). In the present work, a combination of electronic structure calculations, direct dynamics calculations, and experimental studies was carried out to investigate how chloroform acts as a hydrogen atom donor in Barton reductive decarboxylations and to determine the scope of this process. The results from this study show that hydrogen atom transfer from chloroform occurs directly under kinetic control and is aided by a combination of polar effects and quantum mechanical tunneling. Chloroform acts as an effective hydrogen atom donor for primary, secondary, and tertiary alkyl radicals, although significant chlorination was also observed with unstrained tertiary carboxylic acids.
NMO·TPB: A selectivity variation on the Ley-Griffith TPAP oxidation
Publisher: Wiley
Date: 21-01-2015
Abstract: A non-hygroscopic tetraphenylborate salt of N-methylmorpholine-N-oxide (NMO) is reported (NMO⋅TPB), which modulates the standard Ley-Griffith oxidation such that benzylic and allylic alcohols are oxidised selectively. An attractive feature of this new protocol is that anhydrous conditions are not required for this selective tetra-n-propylammonium perruthenate (TPAP) oxidation, superseding the requirement of molecular sieves.
Activation of PKC supports the anticancer activity of tigilanol tiglate and related epoxytiglianes
Publisher: Springer Science and Business Media LLC
Date: 08-01-2021
DOI: 10.1038/S41598-020-80397-9
Abstract: The long-standing perception of Protein Kinase C (PKC) as a family of oncoproteins has increasingly been challenged by evidence that some PKC isoforms may act as tumor suppressors. To explore the hypothesis that activation, rather than inhibition, of these isoforms is critical for anticancer activity, we isolated and characterized a family of 16 novel phorboids closely-related to tigilanol tiglate (EBC-46), a PKC-activating epoxytigliane showing promising clinical safety and efficacy for intratumoral treatment of cancers. While alkyl branching features of the C12-ester influenced potency, the 6,7-epoxide structural motif and position was critical to PKC activation in vitro. A subset of the 6,7-epoxytiglianes were efficacious against established tumors in mice which generally correlated with in vitro activation of PKC. Importantly, epoxytiglianes without evidence of PKC activation showed limited antitumor efficacy. Taken together, these findings provide a strong rationale to reassess the role of PKC isoforms in cancer, and suggest in some situations their activation can be a promising strategy for anticancer drug discovery.
A new synthesis of chiral aminoalkyloxazolecarboxylate esters from isoxazol-5(2H)-ones: the synthesis of almazoles A and B
Publisher: Elsevier BV
Date: 07-1998
Oxidative degradation of benzene rings
Publisher: Elsevier BV
Date: 02-2003
Pressurized honeycombs as soft-actuators: a theoretical study
Publisher: The Royal Society
Date: 06-09-2014
Abstract: The seed capsule of Delosperma nakurense is a remarkable ex le of a natural hygromorph, which unfolds its protecting valves upon wetting to expose its seeds. The beautiful mechanism responsible for this motion is generated by a specialized organ based on an anisotropic cellular tissue filled with a highly swelling material. Inspired by this system, we study the mechanics of a diamond honeycomb internally pressurized by a fluid phase. Numerical homogenization by means of iterative finite-element (FE) simulations is adapted to the case of cellular materials filled with a variable pressure fluid phase. Like its biological counterpart, it is shown that the material architecture controls and guides the otherwise unspecific isotropic expansion of the fluid. Deformations up to twice the original dimensions can be achieved by simply setting the value of input pressure. In turn, these deformations cause a marked change of the honeycomb geometry and hence promote a stiffening of the material along the weak direction. To understand the mechanism further, we also developed a micromechanical model based on the Born model for crystal elasticity to find an explicit relation between honeycomb geometry, swelling eigenstrains and elastic properties. The micromechanical model is in good qualitative agreement with the FE simulations. Moreover, we also provide the force-stroke characteristics of a soft actuator based on the pressurized anisotropic honeycomb and show how the internal pressure has a nonlinear effect which can result in negative values of the in-plane Poisson's ratio. As nature shows in the case of the D. nakurense seed capsule, cellular materials can be used not only as low-weight structural materials, but also as simple but convenient actuating materials.
ATP3 and MTP3: Easily Prepared Stable Perruthenate Salts for Oxidation Applications in Synthesis
Publisher: Wiley
Date: 06-03-2018
Abstract: The Ley-Griffith tetra-n-propylammonium perruthenate (TPAP) catalyst has been widely deployed by the synthesis community, mainly for the oxidation of alcohols to aldehydes and ketones, but also for a variety of other synthetic transformations (e.g. diol cleavage, isomerizations, imine formation and heterocyclic synthesis). Such popularity has been forged on broad reaction scope, functional group tolerance, mild conditions, and commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and MTP3) that mirror the reactivity of TPAP, but avoid storage decomposition issues.
Synthetic neovibsanes and their ability to induce neuronal differentiation in PC12 cells
Publisher: Elsevier BV
Date: 08-2010
A General Procedure to Access Methylene Ether Isonitrile Derivatives
Publisher: Georg Thieme Verlag KG
Date: 25-09-2008
Isolation and confirmation of the proposed cleistanthol biogentic link from Croton insularis.
Publisher: American Chemical Society (ACS)
Date: 04-02-2011
DOI: 10.1021/OL103083M
Abstract: The proposed cleistanthol biosynthetic intermediate en route to spruceanol, and other related family members, was isolated for the first time from Croton insularis, confirming the Jacobs-Reynolds hypothesis. Anticancer evaluation of the new isolates and their aerial oxidation products is also reported.
The First Plant 5,6‐Secosteroid from the Australian Arid Zone Species Frankenia foliosa
Publisher: Wiley
Date: 17-03-2017
Climate‐Dependent Heat‐Triggered Opening Mechanism of Banksia Seed Pods
Publisher: Wiley
Date: 13-12-2017
Synthesis of the seco ‐Limonoid BCD Ring System Identifies a Hsp90 Chaperon Machinery (p23) Inhibitor
Publisher: Wiley
Date: 20-12-2018
Abstract: D-Ring-seco-limonoids (tetranortriterpenoids), such as gedunin and xylogranin B display anti-cancer activity, acting via inhibition of Hsp90 and/or associated chaperon machinery (e.g., p23). Despite this, these natural products have received relatively little attention, both in terms of an enabling synthetic approach (which would allow access to derivatives), and as a consequence their structure-activity relationship (SAR). Disclosed herein is a generally applicable synthetic route to the BCD ring system of the seco-D-ring double bond containing limonoids. Furthermore, cell based assays revealed the first skeletal fragment that exhibited inhibition of the p23 enzyme at a level which was equipotent to that of gedunin, despite being much less structurally complex.
EBC-219: a new diterpene skeleton, crotinsulidane, from the Australian rainforest containing a bridgehead double bond.
Publisher: Wiley
Date: 05-05-2014
Abstract: EBC-219 (4), isolated from Croton insularis (Baill), was established by spectroscopic and DFT methods as the first member of a new diterpene skeletal class, uniquely defined by the presence of a bicyclo[10.2.1] bridgehead olefin. The proposed biogenetic pathway to 4 from the co-isolated natural products EBC-131 (1), EBC-180 (2) and EBC-181 (3) is highly likely. EBC-180 (2) and EBC-181 (3) showed moderate to strong cytotoxic activity against various cancer cell lines.
Furofuran lignans from the Simpson Desert species Eremophila macdonnellii
Publisher: Elsevier BV
Date: 04-2018
DOI: 10.1016/J.FITOTE.2017.06.004
Abstract: The Eremophila plant family, which occurs in the arid zones of Australia, have witnessed extensive investigation, mostly inspired by Aboriginal traditional medicine. A wide and varied biological and phytochemical profile has been reported for over 18 in idual species of Australian Eremophila, although E. macdonnellii from the Simpson Desert has not yet been investigated. Isolation and elucidation of one new and six known furofuran lignans are reported. The new lignan, epimethoxypiperitol, displayed moderate anti-cancer activity against the breast cancer cell line (MCF-7).
The First Casbane Hydroperoxides EBC-304 and EBC-320 from the Australian Rainforest.
Publisher: Wiley
Date: 07-12-2016
Abstract: Investigation of the Australian rainforest plant Croton insularis led to isolation of the first casbane hydroperoxide diterpenes EBC-304 and EBC-320. Extensive DFT and electronic circular dichroism (ECD) calculations in combination with 2D NMR spectroscopy determined the absolute configurations. EBC-304 and EBC-320 both display significant cytotoxicity.
Structures of fungal and plant acetohydroxyacid synthases
Publisher: Springer Science and Business Media LLC
Date: 08-07-2020
7th Heron Island Conference on Reactive Intermediates and Unusual Molecules
Publisher: CSIRO Publishing
Date: 2017
DOI: 10.1071/CH17065
Mechanistic aspects of the lycopodine Michael-Claisen domino cyclization
Publisher: Springer Science and Business Media LLC
Date: 16-03-2014
DOI: 10.1007/S00894-014-2173-0
Abstract: The Michael-Claisen domino (MCD) cyclization used in the lycopodine synthesis by Stork, was evaluated mechanistically using DFT calculations. Calculations suggest that a dianion is not formed, which conforms to classical dianion formation normally requiring strong kinetic bases. Instead ethoxide in ethanol produces a monoanionic species driving the MCD cyclization. This endeavor has opened up potential to expand the scope of this unique reaction and provide educational clarity.
Selectivity Modulation of the Ley–Griffith TPAP Oxidation with N ‐Oxide Salts
Publisher: Wiley
Date: 27-06-2016
Total Synthesis of (±)-4,5-Bis-epi-Neovibsanin A and B: A Neurite Outgrowth Comparison Study
Publisher: American Chemical Society (ACS)
Date: 20-08-2009
DOI: 10.1021/OL901406J
Abstract: (+/-)-4,5-Bis-epi-neovibsanin A and B were synthesized in 12 steps. The acid-catalyzed, one-pot, five-step cascade reaction was central toward the formation of the tricyclic core. The two diastereomers of natural neovibsanin A and B acted as desirable derivatives for structure-activity relationship studies to probe neurotrophic activity. Both (+/-)-4,5-bis-epi-neovibsanin A and B strongly potentiate neurite outgrowth in NGF-stimulated PC12 cells. Furthermore, the tricyclic core appears to be largely responsible for promoting a biological response.
Stachyonic Acid: A Dengue Virus Inhibitor from Basilicum polystachyon
Publisher: Wiley
Date: 29-03-2019
Abstract: Stachyonic acid A, arising from the first in-depth phytochemical investigation of the herb Basilicum polystachyon, was found to display potent inhibitory activity against dengue virus, with limited cytotoxicity. Andrographolide, a known dengue virus inhibitor and closely related labdane-type diterpene, is structurally more complex but displayed poor antiviral activity in the PRNT assay, and increased cytotoxicity in comparison. Furthermore, a Diels-Alder reaction with PTAD identified the active pharmacophore of stachyonic acid to be the conjugated diene.
Towards the Total Synthesis of Vibsanin E, 15‐O‐Methylcyclovibsanin B,3‐Hydroxyvibsanin E, Furanovibsanin A, and 3‐O‐Methylfuranovibsanin A
Publisher: Wiley
Date: 26-06-2006
Abstract: Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin‐type diterpenes (i.e. vibsanin E, 15‐ O ‐methylcyclovibsanin B, 3‐hydroxy‐vibsanin E, furanovibsanin A, and 3‐ O ‐methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six‐ to seven‐membered ring‐expansion protocols, which gain access to the central core of these natural products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Total Synthesis of (±)-2-O-Methylneovibsanin H
Publisher: American Chemical Society (ACS)
Date: 12-07-2008
DOI: 10.1021/OL801117E
Abstract: The total synthesis of (+/-)-2- O-methylneovibsanin H was achieved in 12 steps. An acid-catalyzed, one-pot, four-step cascade reaction was key to the concise total synthesis, lending support to the proposed biosynthesis.
Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: Application to the Total Synthesis of the Natural Product (−)-5-epi-Vibsanin E
Publisher: American Chemical Society (ACS)
Date: 15-05-2009
DOI: 10.1021/JA9019484
Front cover: developing cyclic peptide heteroatom interchange: synthesis and DFT modelling of a HI-ascidiacyclamide isomer (Eur. J. Org. Chem. /2018)
Publisher: Wiley
Date: 19-06-2018
Comprehensive Computational Investigation of the Barton–Kellogg Reaction for Both Alkyl and Aryl Systems
Publisher: American Chemical Society (ACS)
Date: 20-05-2021
A Protocol for an Iodine–Metal Exchange Reaction on Cubane Using Lithium Organozincates
Publisher: American Chemical Society (ACS)
Date: 10-01-2019
DOI: 10.1021/ACS.ORGLETT.8B03721
Abstract: The iodine-metal exchange reaction on cubane was examined using various lithium organozincates. Among these, the dianionic zincate, n-Bu
The future of retrosynthesis and synthetic planning: algorithmic, humanistic or the interplay?
Publisher: CSIRO Publishing
Date: 12-05-2021
DOI: 10.1071/CH20371
Abstract: The practice of deploying and teaching retrosynthesis is on the cusp of considerable change, which in turn forces practitioners and educators to contemplate whether this impending change will advance or erode the efficiency and elegance of organic synthesis in the future. A short treatise is presented herein that covers the concept of retrosynthesis, along with exemplified methods and theories, and an attempt to comprehend the impact of artificial intelligence in an era when freely and commercially available retrosynthetic and forward synthesis planning programs are increasingly prevalent. Will the computer ever compete with human retrosynthetic design and the art of organic synthesis?
Frontispiz: Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere
Publisher: Wiley
Date: 29-02-2016
Time-of-flight detection of ultra-cold atoms using resonant frequency modulation imaging
Publisher: The Optical Society
Date: 20-05-2016
DOI: 10.1364/OL.41.002505
The Synthesis of Almazoles A and B
Publisher: CSIRO Publishing
Date: 1999
DOI: 10.1071/C98093
Abstract: Almazoles A (1) and B (2) are formed in seven steps from phenylalanine without any racemization. The key step is the N-acylation of the isoxazol-5(2H)-one (5) with the phthalimide-protected amino acid, and photolysis of the product at 300 nm in acetone.
End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A
Publisher: Beilstein Institut
Date: 08-10-2008
DOI: 10.3762/BJOC.4.34
Crystal Structure of the Commercial Herbicide, Amidosulfuron, in Complex with Arabidopsis thaliana Acetohydroxyacid Synthase
Publisher: American Chemical Society (ACS)
Date: 21-03-2023
Herbicides That Target Acetohydroxyacid Synthase Are Potent Inhibitors of the Growth of Drug-Resistant Candida auris
Publisher: American Chemical Society (ACS)
Date: 28-09-2020
Geometry as a Factor for Tissue Growth: Towards Shape Optimization of Tissue Engineering Scaffolds
Publisher: Wiley
Date: 19-11-2013
The Synthesis and X-ray Crystal Structure of 6-Bromo-2,4,4-Trimethyl-Cyclohex-2-Enone
Publisher: SAGE Publications
Date: 07-2003
DOI: 10.3184/030823403103174326
Abstract: Regiospecific bromination of 2,4,4-trimethyl-cyclohex-2-enone was achieved and the X-ray crystal structure of 6-bromo-2,4,4-trimethyl-cyclohex-2-enone is presented.
Microenvironment-mediated cancer dormancy: Insights from metastability theory
Publisher: Proceedings of the National Academy of Sciences
Date: 23-12-2021
Abstract: Dormancy is an evolutionarily conserved protective mechanism widely observed in nature. A pathological ex le is found during cancer metastasis, where cancer cells disseminate from the primary tumor, home to secondary organs, and enter a growth-arrested state, which could last for decades. Recent studies have pointed toward the microenvironment being heavily involved in inducing, preserving, or ceasing this dormant state, with a strong focus on identifying specific molecular mechanisms and signaling pathways. Increasing evidence now suggests the existence of an interplay between intracellular as well as extracellular biochemical and mechanical cues in guiding such processes. Despite the inherent complexities associated with dormancy, proliferation, and growth of cancer cells and tumor tissues, viewing these phenomena from a physical perspective allows for a more global description, independent from many details of the systems. Building on the analogies between tissues and fluids and thermodynamic phase separation concepts, we classify a number of proposed mechanisms in terms of a thermodynamic metastability of the tumor with respect to growth. This can be governed by interaction with the microenvironment in the form of adherence (wetting) to a substrate or by mechanical confinement of the surrounding extracellular matrix. By drawing parallels with clinical and experimental data, we advance the notion that the local energy minima, or metastable states, emerging in the tissue droplet growth kinetics can be associated with a dormant state. Despite its simplicity, the provided framework captures several aspects associated with cancer dormancy and tumor growth.
Cubane, Bicyclo[1.1.1]pentane and Bicyclo[2.2.2]octane: Impact and Thermal Sensitiveness of Carboxyl‐, Hydroxymethyl‐ and Iodo‐substituents
Publisher: Wiley
Date: 20-08-2020
Abstract: With the burgeoning interest in cage motifs for bioactive molecule discovery, and the recent disclosure of 1,4‐cubane‐dicarboxylic acid impact sensitivity, more research into the safety profiles of cage scaffolds is required. Therefore, the impact sensitivity and thermal decomposition behavior of judiciously selected starting materials and synthetic intermediates of cubane, bicyclo[1.1.1]pentane (BCP), and bicyclo[2.2.2]octane (BCO) were evaluated via hammer test and sealed cell differential scanning calorimetry, respectively. Iodo‐substituted systems were found to be more impact sensitive, whereas hydroxymethyl substitution led to more rapid thermodecomposition. Cubane was more likely to be impact sensitive with these substituents, followed by BCP, whereas all BCOs were unresponsive. The majority of derivatives were placed substantially above Yoshida thresholds—a computational indicator of sensitivity.
Pharmaceuticals that contain polycyclic hydrocarbon scaffolds
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CS00477A
Abstract: This review comprehensively explores approved pharmaceutical compounds that contain polycyclic scaffolds and the properties that these skeletons convey.
Silver Alkyls, Alkenyls, Aryls, and Alkynyls in Organic Synthesis
Publisher: Wiley
Date: 23-07-2010
ChemInform Abstract: Selectivity Modulation of the Ley-Griffith TPAP Oxidation with N-Oxide Salts.
Publisher: Wiley
Date: 09-2016
Investigating direct routes to an advanced intermediate for the synthesis of C-20 diterpene alkaloids
Publisher: Elsevier BV
Date: 04-2005
Nitrogen is a requirement for the photochemical induced 3-azabicyclo[3.3.1]nonane skeletal rearrangement!
Publisher: Elsevier BV
Date: 04-2005
Scaffold curvature-mediated novel biomineralization process originates a continuous soft tissue-to-bone interface
Publisher: Elsevier BV
Date: 09-2017
DOI: 10.1016/J.ACTBIO.2017.07.029
Abstract: A myriad of shapes are found in biological tissues, often naturally evolved to fulfill a particular function. In the field of tissue engineering, substrate geometry influences cell behavior and tissue formation in vitro, yet little is known how this translates to an in vivo scenario. Here we investigate scaffold curvature-induced tissue growth, without additional growth factors or cells, in an ovine animal model. We show that soft tissue formation follows a curvature-driven tissue growth model. The highly organized endogenous soft matrix, potentially under mechanical strain, leads to a non-standard form of biomineralization, whereby the pre-existing organic matrix is mineralized without collagen remodeling and without an intermediate cartilage ossification phase. Micro- and nanoscale characterization of the tissue microstructure using histology, backscattered electron (BSE) and second-harmonic generation (SHG) imaging and synchrotron small angle X-ray scattering (SAXS) revealed (i) continuous collagen fibers across the soft-hard tissue interface on the tip of mineralized cones, and (ii) bone remodeling by basic multicellular units (BMUs) in regions adjacent to the native cortical bone. Thus, features of soft tissue-to-bone interface resembling the insertion sites of ligaments and tendons into bone were created, using a scaffold that did not mimic the structural or biological gradients across such a complex interface at its mature state. This study provides fundamental knowledge for biomimetic scaffold design in the fields of bone regeneration and soft tissue-to-bone interface tissue engineering. Geometry influences cell behavior and tissue formation in vitro. However, little is known how this translates to an in vivo scenario. Here we investigate the influence of scaffold mean surface curvature on in vivo tissue growth using an ovine animal model. Based on a multiscale tissue microstructure characterization, we show a seamless integration of soft tissue into newly formed bone, resembling the insertion sites of ligaments and tendons into bone. This interface was created using a scaffold without additional growth factors or cells that did not recapitulate the structural or biological gradients across such a complex tissue interface at its mature state. These findings have important implications for biomimetic scaffold design for bone regeneration and soft tissue-to-bone interface tissue engineering.
Modelling the role of surface stress on the kinetics of tissue growth in confined geometries
Publisher: Elsevier BV
Date: 03-2013
[4+2] Cycloaddition Reactions Between 1,8‐Disubstituted Cyclooctatetraenes and Diazo Dienophiles: Stereoelectronic Effects, Anticancer Properties and Application to the Synthesis of 7,8‐Substituted Bi
Publisher: Wiley
Date: 29-07-2010
Abstract: A detailed examination of [4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo compounds revealed that 4-phenyl-1,2,4-triazole-3,5-dione (PTAD) reacts to form either 2,3- or 3,4-disubstituted adducts. The product distribution can be controlled by modulating the electron density of the cyclooctatetraene. Unprecedented [4+2] cycloadditions between diisopropyl azodicarboxylate (DIAD) and 1,8-disubstituted cyclooctatetraenes are also described and further manipulation of a resulting cycloadduct uncovered a new pathway to the synthetically challenging bicyclo[4.2.0]octa-2,4-diene family. Variation of the substituents resulted in a range of compounds displaying selective action against different human tumour cell types.
EBC‐232 and 323: A Structural Conundrum Necessitating Unification of Five In Silico Prediction and Elucidation Methods**
Publisher: Wiley
Date: 30-08-2020
Abstract: Structurally unique halimanes EBC‐232 and EBC‐323, isolated from the Australian rainforest plant Croton insularis , proved considerably difficult to elucidate. The two diastereomers, which consist an unusual oxo‐6,7‐spiro ring system fused to a dihydrofuran, were solved by unification and consultation of five in silico NMR elucidation and prediction methods [i.e., ACDLabs, olefin strain energy (OSE), DP4, DU8+ and TD DFT CD]. Structure elucidation challenges of this nature are prime test case ex les for empowering future AI learning in structure elucidation.
Determining the necessity of phenyl ring π-character in warfarin
Publisher: Elsevier BV
Date: 08-2019
Rhodium‐Catalyzed [4+3] Cycloaddition to Furans: Direct Access to Functionalized Bicyclo[5.3.0]decane Derivatives
Publisher: Wiley
Date: 13-11-2015
Arneroma B: Structure reassignment and total synthesis
Publisher: Elsevier BV
Date: 10-2023
1-(Phenylethynyl)adamantane
Publisher: International Union of Crystallography (IUCr)
Date: 30-11-2002
Cubane Chirality via Substitution of a “Hidden” Regular Tetrahedron
Publisher: American Chemical Society (ACS)
Date: 21-05-2020
1,2,4-Triazine vs. 1,3- and 1,4-Oxazinones in Normal- and Inverse-Electron-Demand Hetero-Diels-Alder Reactions: Establishing a Status Quo by Computational Analysis
Publisher: Wiley
Date: 22-12-2010
Easy access to various substituted 4-aminocyclopentenes by rearrangement of 2-ethenyl-substituted cyclopropylamines
Publisher: Royal Society of Chemistry (RSC)
Date: 1998
DOI: 10.1039/A807012A
Investigating direct alkynylation at the bridgehead of bicyclic cages using silver(I) acetylides
Publisher: Wiley
Date: 18-12-2007
Abstract: Silver(I) acetylides facilitate direct carbon–carbon bond formation at the bridgehead position of adamantane, and in some instances related systems such as carborate anions and bicyclo[2.2.2]octanes. Substrate constraints along with attempts to further understand the underlying mechanism are presented. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Kalparinol, a Salvialane (Isodaucane) Sesquiterpenoid Derived from Native Australian Dysphania Species That Suggests a Putative Biogenetic Link to Zerumbone
Publisher: American Chemical Society (ACS)
Date: 17-04-2020
Temperature-induced self-sealing capability of Banksia follicles
Publisher: The Royal Society
Date: 06-2018
Abstract: Many plants in fire-prone regions retain their seeds in woody fruits in the plant canopy until the passage of a fire causes the fruit to open and release the seeds. To enable this function, suitable tissues are required that effectively store and protect seeds until they are released. Here, we show that three different species of the Australian genus Banksia incorporate waxes at the interface of the two valves of the follicle enclosing the seeds, which melt between 45°C and 55°C. Since the melting temperature of the waxes is lower than the opening temperatures of the follicles in all investigated species ( B. candolleana , B. serrata , B. attenuata ), we propose that melting of these waxes allows the sealing of micro-fissures at the interface of the two valves while they are still closed. Such a self-sealing mechanism likely contributes to the structural integrity of the seed pods, and benefits seed viability and persistence during storage on the plants. Furthermore, we show in a simplified, bioinspired model system that temperature treatments seal artificially applied surface cuts and restore the barrier properties.
A novel vitamin K derived anticoagulant tolerant to genetic variations of vitamin K epoxide reductase
Publisher: Elsevier BV
Date: 03-2021
DOI: 10.1111/JTH.15209
Correction: The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8NP90041H
Abstract: Correction for ‘The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research’ by James B. McAlpine et al. , Nat. Prod. Rep. , 2018, DOI: 10.1039/c7np00064b.
Croton insularis introduces the seco-casbane class with EBC-329 and the first casbane endoperoxide EBC-324.
Publisher: Royal Society of Chemistry (RSC)
Date: 02-09-2014
DOI: 10.1039/C4CC05413J
Abstract: Investigation of Croton insularis afforded the first in class seco-casbane diterpene, EBC-329. A highly oxidised casbane, EBC-324, was also isolated. The structural motif within EBC-324, which consists of an epoxidised hemi-acetal endoperoxide, is new to the casbane family.
One-step alkynylation of adamantyl iodide with silver(I) acetylides
Publisher: American Chemical Society (ACS)
Date: 03-2005
DOI: 10.1021/OL050121+
New Halimanes from the Australian Rainforest Plant Croton Insularis
Publisher: Wiley
Date: 07-01-2019
Corrigendum: Ranking Oxidant Sensitiveness: A Guide for Synthetic Utility
Publisher: Wiley
Date: 10-2020
An improved preparation of phorbol from croton oil
Publisher: Beilstein Institut
Date: 11-07-2017
DOI: 10.3762/BJOC.13.133
Abstract: Background: Croton oil is the only commercial source of the diterpenoid phorbol ( 1a ), the starting material for the semi-synthesis of various diesters extensively used in biomedical research to investigate cell function and to evaluate in vivo anti-inflammatory activity. While efficient chemoselective esterification protocols have been developed for phorbol, its isolation from croton oil is technically complicated, and involves extensive manipulation of very toxic materials like the oil or its native diterpenoid fraction. Results: The preparation of a crude non-irritant phorboid mixture from croton oil was telescoped to only five operational steps, and phorbol could then be purified by gravity column chromatography and crystallization. Evidence is provided that two distinct phorboid chemotypes of croton oil exist, differing in the relative proportion of type-A and type-B esters and showing different stability to deacylation. Conclusion: The isolation of phorbol from croton oil is dangerous because of the toxic properties of the oil, poorly reproducible because of differences in its phorboid profile, and time-consuming because of the capricious final crystallization step. A solution for these issues is provided, suggesting that the poor-reproducibility of croton oil-based anti-inflammatory assays are the result of poor quality and/or inconsistent composition of croton oil.
6th Heron Island Conference on Reactive Intermediates and Unusual Molecules
Publisher: CSIRO Publishing
Date: 2014
DOI: 10.1071/CH14041
Structure and absolute stereochemistry of the anticancer agent EBC-23 from the Australian rainforest.
Publisher: American Chemical Society (ACS)
Date: 25-10-2008
DOI: 10.1021/JA807133P
Abstract: EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.
Intramolecular Titanium-Mediated Aminocyclopropanation of Terminal Alkenes: Easy Access to Various Substituted Azabicyclo[n.1.0]alkanes1
Publisher: American Chemical Society (ACS)
Date: 21-01-2003
DOI: 10.1021/OL027352Q
Abstract: [reaction: see text] A variety of substituted azabicyclo[n.1.0]alkanes were synthesized by intramolecular titanium-mediated cyclopropanation of N-benzyl-N-(2-alkylalk-3-enyl)formamides and N-benzyl-N-alkadienylformamides. N-Benzylpyrroline upon treatment with Grignard reagents undergoes a titanium-mediated carbomagnesiation to yield N-benzyl-N-(2-alkylbut-3-enyl)amines.
Guaiacol transprotection: replacement of the phenoxy isopropyl protecting function by acetyl
Publisher: Elsevier BV
Date: 2004
Determining a Synthetic Approach to Pierisformaside C
Publisher: American Chemical Society (ACS)
Date: 12-09-2011
DOI: 10.1021/OL202147R
Abstract: An efficient route detailing the construction of the central core of pierisformaside C, the first grayanane-type diterpene to possess three central double bonds, is reported.
Squaramides as Bioisosteres in Contemporary Drug Design
Publisher: American Chemical Society (ACS)
Date: 15-09-2020
Cubane: A New NMR Internal Standard
Publisher: CSIRO Publishing
Date: 2010
DOI: 10.1071/CH10107
Abstract: Cubane can be considered the ideal internal standard for reactions observed by NMR, due to an almost complete benign reactivity and uniquely reliable 1H and 13C NMR resonances, in wide variety of deuterated solvents.
Do anti-Bredt natural products exist? Olefin strain energy as a predictor of isolability
Publisher: Wiley
Date: 29-07-2015
Abstract: Bredt's rule holds a special place in the realm of physical organic chemistry, but its application to natural products chemistry—the field in which the rule was originally formulated—is not well defined. Herein, the use of olefin strain (OS) energy as a readily calculated predictor of the stability of natural products containing a bridgehead alkene is introduced. Schleyer first used OS energies to classify parent bridgehead alkenes into "isolable", "observable", and "unstable" classes. OS calculations on natural products, using contemporary forcefield methods, unequivocally predict all structurally verified bridgehead alkene natural products to be "isolable". Thus, when one assigns the structure of a putative bridgehead alkene natural product, an OS in the "observable" or "unstable" ranges is a red flag for error.
Cyclooctatetraene: A Bioactive Cubane Paradigm Complement
Publisher: Wiley
Date: 25-01-2019
Product Class 9: Acridines
Publisher: Georg Thieme Verlag
Date: 2005
An Unprecedented Stereoselective Titanium-Mediated Dihydrodimerization of Allyl Ethers and Allylamines
Publisher: Georg Thieme Verlag KG
Date: 2000
DOI: 10.1055/S-2000-6297
seco-1-Azacubane-2-carboxylic acid–Amide Bond Comparison to Proline
Publisher: American Chemical Society (ACS)
Date: 30-08-2023
In Vitro Metabolic Stability and in Vivo Biodistribution of 3-Methyl-4-furoxancarbaldehyde Using PET Imaging in Rats
Publisher: American Chemical Society (ACS)
Date: 12-04-2016
A genome-wide CRISPR-Cas9 knockout screen identifies FSP1 as the warfarin-resistant vitamin K reductase
Publisher: Springer Science and Business Media LLC
Date: 14-02-2023
DOI: 10.1038/S41467-023-36446-8
Abstract: Vitamin K is a vital micronutrient implicated in a variety of human diseases. Warfarin, a vitamin K antagonist, is the most commonly prescribed oral anticoagulant. Patients overdosed on warfarin can be rescued by administering high doses of vitamin K because of the existence of a warfarin-resistant vitamin K reductase. Despite the functional discovery of vitamin K reductase over eight decades ago, its identity remained elusive. Here, we report the identification of warfarin-resistant vitamin K reductase using a genome-wide CRISPR-Cas9 knockout screen with a vitamin K-dependent apoptotic reporter cell line. We find that ferroptosis suppressor protein 1 (FSP1), a ubiquinone oxidoreductase, is the enzyme responsible for vitamin K reduction in a warfarin-resistant manner, consistent with a recent discovery by Mishima et al. FSP1 inhibitor that inhibited ubiquinone reduction and thus triggered cancer cell ferroptosis, displays strong inhibition of vitamin K-dependent carboxylation. Intriguingly, dihydroorotate dehydrogenase, another ubiquinone-associated ferroptosis suppressor protein parallel to the function of FSP1, does not support vitamin K-dependent carboxylation. These findings provide new insights into selectively controlling the physiological and pathological processes involving electron transfers mediated by vitamin K and ubiquinone.
Developing Cyclic Peptide Heteroatom Interchange: Synthesis and DFT Modelling of a HI‐Ascidiacyclamide Isomer
Publisher: Wiley
Date: 15-06-2018
Towards the Total Synthesis of Spirovibsanin A: Total Synthesis of (±)-5,14-Bis-epi-spirovibsanin A
Publisher: Wiley
Date: 09-2008
Investigating Direct Access to 2-Oxospiro[4.5]decanones via 6π-Electrocyclisation
Publisher: Wiley
Date: 10-2007
Synthesis of novel 2-amino-1,3-thiazole-5-carboxylates utilising ultrasonic and thermally mediated aminolysis
Publisher: Wiley
Date: 03-2003
Elucidating the mechanism of the Ley–Griffith (TPAP) alcohol oxidation
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7SC04260D
Abstract: The mechanism of the Ley–Griffith alcohol oxidation has been elucidated using time-resolved spectroscopic methods.
Nano‐ to Macroscale Remodeling of Functional Tissue‐Engineered Bone
Publisher: Wiley
Date: 08-11-2012
A convenient new route to enantiopure 3-hydroxy-5-oxo esters and 5,6-dihydropyran-2-ones: intricacies of the trithioorthoester protecting group
Publisher: Elsevier BV
Date: 02-2010
EBC-318 and 339: Bicyclo[10.2.1]alkanes from Croton insularis
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6RA02599D
Abstract: EBC-318 and EBC-339 were isolated from Croton insularis , an Australian rain forest plant. EBC-318 is characterised by a bridgehead double bond.
Expedient Construction of the Vibsanin E Core without the Use of Protecting Groups
Publisher: American Chemical Society (ACS)
Date: 03-2005
DOI: 10.1021/OL0501222
Abstract: [reaction: see text] The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaïed Baylis-Hillman variant was key to allowing the Brønsted acid induced tandem cyclization forming rings B and C in one operation.
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Amount: $334,425.00
Funder: Australian Research Council
View Funded ActivityDiscovery Projects - Grant ID: DP130103858
Start Date: 2013
End Date: 12-2016
Amount: $400,000.00
Funder: Australian Research Council
View Funded ActivitySpecial Research Initiatives - Grant ID: SR0354908
Start Date: 2004
End Date: 12-2004
Amount: $10,000.00
Funder: Australian Research Council
View Funded ActivityLinkage Infrastructure, Equipment And Facilities - Grant ID: LE160100218
Start Date: 2016
End Date: 12-2016
Amount: $840,000.00
Funder: Australian Research Council
View Funded Activity