ORCID Profile
0000-0003-1100-4544
Current Organisation
University of Sydney
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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)
Macromolecular and Materials Chemistry | Nanochemistry and Supramolecular Chemistry | Organic Chemical Synthesis | Organic Chemistry | Organic Chemical Synthesis | Supramolecular Chemistry | Biochemistry and Cell Biology | Synthesis of Materials | Sensor Technology (Chemical aspects) | Physical Chemistry (Incl. Structural) | Structural Chemistry and Spectroscopy | Structural Biology (incl. Macromolecular Modelling) | Analytical Chemistry | Structural Chemistry | Physical Chemistry of Materials | Characterisation of Biological Macromolecules | Optical Properties of Materials | Medicinal and Biomolecular Chemistry | Biomechanical Engineering | Electroanalytical Chemistry | Physical Organic Chemistry | Proteins and Peptides | Receptors and Membrane Biology | Signal Transduction | Protein Trafficking | Proteomics and Intermolecular Interactions (excl. Medical Proteomics) | Inorganic Chemistry Not Elsewhere Classified | Analytical Chemistry Not Elsewhere Classified | Organic Chemistry Not Elsewhere Classified | Cell Development, Proliferation and Death
ANZSRC Socio-Economic Objective (SEO)
Expanding Knowledge in the Chemical Sciences | Chemical sciences | Biological sciences | Expanding Knowledge in the Biological Sciences | Control of Animal Pests, Diseases and Exotic Species in Farmland, Arable Cropland and Permanent Cropland Environments | Higher education | Water Recycling Services (incl. Sewage and Greywater) | Human Pharmaceutical Treatments (e.g. Antibiotics) | Plastics in Primary Forms | Expanding Knowledge in the Physical Sciences |
Related Links
Publications
Assembly of a trinuclear metallo-capsule from a tripodal tris(β-diketone) derivative and copper(ii)
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B717685F
Abstract: A new metallo-capsule has been synthesised that consists of three copper(II) ions and two molecules of a tris-deprotonated tripodal ligand in which three 2,4-pentanedione groups are linked via their gamma-carbons through thioether spacers to the 1,3,5-positions of a triazine core.
Synthesis of the Sialic Acid (−)-KDN and Certain Epimers from (−)-3-Dehydroshikimic Acid or (−)-Quinic Acid
Publisher: American Chemical Society (ACS)
Date: 14-07-2004
DOI: 10.1021/OL049048Y
Abstract: (-)-3-Dehydroshikimic acid (3-DHS, 4), a C(7)-building block now available in large quantity from corn syrup, has been converted into the sialic acid (-)-KDN (3) as well as its C-7- and C-8-epimers. (-)-Quinic acid can be used for the same purpose. [structure: see text]
Photoinduced Energy and Electron Transfer in a Giant Zinc Porphyrin−Bridge−C60 System
Publisher: American Chemical Society (ACS)
Date: 10-2002
DOI: 10.1021/JP014155K
Macrocyclic squaramides: Anion receptors with high sulfate binding affinity and selectivity in aqueous media
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6SC01011C
Abstract: Macrocyclic squaramide derivatives bind sulfate ions with high selectivity and affinity in aqueous mixtures.
Amino acid-based squaramides for anion recognition
Publisher: Informa UK Limited
Date: 17-11-2015
Electroactive Co(iii) salen metal complexes and the electrophoretic deposition of their porous organic polymers onto glassy carbon
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8RA04385J
Abstract: We report the synthesis, characterisation and electrochemistry of Co( iii ) salen metal complexes and their porous organic polymers for CO 2 electroreduction.
Proton and anion control of framework complexity in copper(II) complex structures derived from 2-(hydroxymethyl)pyridine
Publisher: Elsevier BV
Date: 02-2007
Total Synthesis and Reassignment of the Structures of the Antimicrobial Lipodepsipeptides Circulocin γ and δ
Publisher: American Chemical Society (ACS)
Date: 15-04-2015
Abstract: The structures of the naturally occurring antimicrobial lipodepsipeptides circulocin γ and circulocin δ have been reported to comprise a common cyclic depsipeptide core attached to 3-hydroxy,ω-guanidino fatty acid chains differing in length by two methylene units, but analysis of the reported data suggested that the originally reported structures had incorrect side chain lengths. The total synthesis of both side chain epimers of the originally reported structure of circulocin γ bearing a 19-guanidino-3-hydroxynonadecanoyl (GHND) side chain has been accomplished using a modular approach involving synthesis of the cyclic depsipeptide and side chain fragments followed by a late stage coupling reaction. This revealed that the originally reported structure for circulocin γ bearing the GHND side chain is incorrect and that this structure is actually that of circulocin δ. It has also enabled the absolute configuration of the side chain hydroxy group of the natural product to be assigned as (R). Subsequent synthesis of the analogue bearing a 17-guanidino-3-(R)-hydroxyheptadecanoyl (GHHD) side chain provided confirmation that this revised structure is that of circulocin γ.
Fragments of the Bacterial Toxin Microcin B17 as Gyrase Poisons
Publisher: Public Library of Science (PLoS)
Date: 10-04-2013
Pyrophosphate Recognition and Sensing in Water Using Bis[zinc(II)dipicolylamino]-Functionalized Peptides
Publisher: American Chemical Society (ACS)
Date: 14-08-2017
DOI: 10.1021/ACS.ACCOUNTS.7B00252
Abstract: Phosphate oxoanions and phosphorylated biomolecules (such as nucleotides, lipids, and proteins) play key roles in a wide range of biological processes. The ability to selectively detect these ions in the presence of each other has numerous applications in biochemistry and biomedicine. However, receptors and sensors that can discriminate between polyphosphate species with high selectivity and in biologically relevant conditions are rare. In this Account, we show how peptides (both cyclic and linear) can be used to position two zinc(II)dipicolylamine [Zn(II)DPA] binding sites in an appropriate arrangement to provide selective binding of pyrophosphate (PPi) in the presence of other polyphosphate species, including ATP, and in complex media such as cell growth buffer. The use of peptide scaffolds to position the Zn(II)DPA anion binding sites allowed the synthesis of small receptor libraries in which the arrangement of the two binding sites could be subtly altered to evaluate the factors affecting both binding selectivity and affinity for PPi. We altered a number of structural elements including peptide length, cyclic peptide ring size, amino acid composition, the positioning of the binding sites with respect to one another, and the relative stereochemistry of the peptides. Backbone modified cyclic peptides based on the Lissoclinum class of natural products were initially employed to provide an added degree of preorganization to the receptors, although it was subsequently found that short, flexible bis[Zn(II)DPA]-functionalized linear peptides are also effective scaffolds for selective pyrophosphate recognition. The peptidic receptors were successfully employed for the detection of PPi in aqueous media by indicator displacement assays using both colorimetric and fluorescent indicators, with the best compounds able to bind to PPi selectively in both cell growth media and artificial urine and also allow the accurate determination of PPi concentrations in physiologically relevant ranges (micromolar concentrations) in these complex media. Improved pyrophosphate selectivity was observed upon increasing the complexity of the media from HEPES buffer to cell growth media (Krebs saline). Pyrophosphate sensors in which a fluorescent indicator was covalently attached to either a linear or cyclic peptide scaffold through a flexible linker were then constructed. When the Zn(II)DPA binding sites and the indicator were suitably placed with respect to one another on the peptide scaffold, these 'intramolecular indicator displacement assays' showed improved selectivity for PPi over other polyphosphate anions, such as ATP, when compared to the intermolecular indicator displacement assays. This observation provides the basis for the design and application of future PPi sensors in biochemistry and biomedicine.
Duale Funktionalisierung von Fluorophoren für die Konstruktion zielgerichteter und selektiver Fluoreszenz‐Sensoren
Publisher: Wiley
Date: 02-09-2020
Ag+ labeling: A convenient new tool for the characterization of hydrogen-bonded supramolecular assemblies by MALDI-TOF mass spectrometry
Publisher: Wiley
Date: 17-11-2000
DOI: 10.1002/1521-3765(20001117)6:22<4104::AID-CHEM4104>3.0.CO;2-Q
Abstract: Herein we describe our results on the characterization of a wide variety of different hydrogen-bonded assemblies by means of a novel matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) technique with Ag+ labeling. The labeling technique with Ag+ ions is extremely mild and provides a nondestructive way to generate charged assemblies that can be detected by mass spectrometry. Up to now more than 25 different single (1(3).2(3)), double (3(3).2(6)), and tetrarosettes (4(3).2(12)) have been successfully characterized by the use of this method. The success of the method entirely depends on the presence of a suitable binding site for the Ag+ ion. A variety of functionalities has been identified that provide strong binding sites for Ag+, either acting in a cooperative way (pi-arene and pi-alkene donor functionalities) or in idually (cyano and crown ether functionalities). The method works well for assemblies with molecular weights between 2,000 and 8,000 Da, and most likely far beyond this limit.
Trifluoroethanethiol: An Additive for Efficient One-Pot Peptide Ligation−Desulfurization Chemistry
Publisher: American Chemical Society (ACS)
Date: 29-05-2014
DOI: 10.1021/JA502806R
Abstract: Native chemical ligation followed by desulfurization is a powerful strategy for the assembly of proteins. Here we describe the development of a high-yielding, one-pot ligation-desulfurization protocol that uses trifluoroethanethiol (TFET) as a novel thiol additive. The synthetic utility of this TFET-enabled methodology is demonstrated by the efficient multi-step one-pot syntheses of two tick-derived proteins, chimadanin and madanin-1, without the need for any intermediary purification.
Extraction and transport of sulfate using macrocyclic squaramide receptors
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/C9SC04786G
Abstract: Lipophilic macrocycles efficiently extract sulfate ions from water into chloroform and transport this ion across a bulk liquid membrane in the presence of competing anions (chloride, nitrate and dihydrogenphosphate).
The potential of ion mobility mass spectrometry for tuning synthetic host guest systems: A case study using novel zinc(II)dipicolylamine anion sensors
Publisher: Elsevier BV
Date: 11-2015
Functional disruption of yeast metacaspase, Mca1, leads to miltefosine resistance and inability to mediate miltefosine-induced apoptotic effects
Publisher: Elsevier BV
Date: 06-2014
DOI: 10.1016/J.FGB.2014.04.003
Abstract: Miltefosine (MI) is a novel, potential antifungal agent with activity against some yeast and filamentous fungal pathogens. We previously demonstrated in the model yeast, Saccharomyces cerevisiae, that MI causes disruption of mitochondrial membrane potential and apoptosis-like cell death via interaction with the Cox9p sub-unit of cytochrome c oxidase (COX). To identify additional mechanisms of antifungal action, MI resistance was induced in S. cerevisiae by exposure to the mutagen, ethyl methanesulfonate, and gene mutation(s) responsible for resistance were investigated. An MI-resistant haploid strain (H-C101) was created. Resistance was retained in the diploid strain (D-C101) following mating, confirming dominant inheritance. Phenotypic assessment of in idual D-C101 tetrads revealed that only one mutant gene contributed to the MI-resistance phenotype. To identify this gene, the genome of H-C101 was sequenced and 17 mutated genes, including metacaspase-encoding MCA1, were identified. The MCA1 mutation resulted in substitution of asparagine (N) with aspartic acid (D) at position 164 (MCA1(N164D)). MI resistance was found to be primarily due to MCA1(N164D), as single-copy episomal expression of MCA1(N164D), but not two other mutated genes (FAS1(T1417I) and BCK2(T104A)), resulted in MI resistance in the wild-type strain. Furthermore, an MCA1 deletion mutant (mca1Δ) was MI-resistant. MI treatment led to accumulation of reactive oxygen species (ROS) in MI-resistant (MCA1(N164D)-expressing and mca1Δ) strains and MI-susceptible (MCA1-expressing) strains, but failed to activate Mca1 in the MI-resistant strains, demonstrating that ROS accumulation does not contribute to the fungicidal effect of MI. In conclusion, functional disruption of Mca1, leads to MI resistance and inability to mediate MI-induced apoptotic effects. Mca1-mediated apoptosis is therefore a major mechanism of MI-induced antifungal action.
Sulfate-selective recognition by using neutral dipeptide anion receptors in aqueous solution
Publisher: Wiley
Date: 14-05-2014
Abstract: The synthesis of six small peptide anion receptors based on thiourea and squaramide recognition moieties is described. These new receptors bind to tetrahedral sulfate anions with remarkable affinity and selectivity in aqueous solution as shown by NMR spectroscopy. Molecular modelling suggests that selectivity is mediated by a hydrogen bond network incorporating the amide backbone protons in a manner similar to that found in the sulfate-binding protein.
A Fluorescent Sensor Array for the Discrimination of Nucleotide Phosphates
Publisher: Wiley
Date: 07-12-2022
Abstract: Chemosensors that can discriminate between nucleotide phosphates are difficult to prepare. Here we describe the use of a sensing array comprising metal complexes of bis(dipicolylamino)‐functionalised linear peptide based fluorescent sensors for the discrimination of nucleotide phosphates. We demonstrate that through the rational incorporation of additional sensor elements the discriminatory power of the array can be improved. An array incorporating two peptides in combination with four metal ions was able to successfully discriminate all triphosphates and diphosphates tested. When monophosphates were included in the analysis, 91 % of the analytes (blank, AMP, ADP, ATP, CMP, CDP, CTP, GMP, GDP, GTP, UMP, UDP and UTP) could be correctly classified, with all classification errors related to monophosphates.
Synthesis and co-crystallisation behaviour of copper(II) complexes of two isomeric p -tolyl-terpyridines
Publisher: Informa UK Limited
Date: 12-12-2007
In vitro activities of miltefosine and two novel antifungal biscationic salts against a panel of 77 dermatophytes
Publisher: American Society for Microbiology
Date: 06-2007
DOI: 10.1128/AAC.01382-06
Abstract: The susceptibilities of 77 dermatophytes to miltefosine (MI), 1,12-bis(4-pentylpyridinium)dodecane (PYR), 1,12-bis(tributylammonium)dodecane (AM), itraconazole (ITC), terbinafine (TRB), and butenafine (BTF) were compared. Geometric mean MICs of TRB, BTF, ITC, MI, PYR, and AM were 0.039, 0.059, 1.718, 0.671, 6.006, and 4.771 μg/ml, respectively. MI was more active than ITC ( P 0.001).
A Fluorogenic Probe for Cell Surface Phosphatidylserine Using an Intramolecular Indicator Displacement Sensing Mechanism
Publisher: Wiley
Date: 13-12-2018
New discrete and polymeric supramolecular architectures derived from dinuclear Co(ii), Ni(ii) and Cu(ii) complexes of aryl-linked bis-β-diketonato ligands and nitrogen bases: synthetic, structural and
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B920199H
Abstract: New ex les of nitrogen base adducts of dinuclear Co(II), Ni(II) and Cu(II) complexes of the doubly deprotonated forms of 1,3-aryl linked bis-beta-diketones of type [RC(=O)CH(2)C(=O)C(6)H(4)C(=O)CH(2)C(=O)R] (L(1)H(2)) incorporating the mono- and difunctional amine bases pyridine (Py), 4-ethylpyridine (EtPy), piperidine (pipi), 1,4-piperazine (pip), N-methylmorpholine (mmorph), 1,4-dimethylpiperazine (dmpip) and N,N,N',N'-tetramethylethylenediamine (tmen) have been synthesised by reaction of the previously reported [Cu(2)(L(1))(2)].2.5THF (R = Me), [Cu(2)(L(1))(2)(THF)(2)] (R = t-Bu), [Ni(2)(L(1))(2)(Py)(4)] (R = t-Bu) and [Co(2)(L(1))(2)(Py)(4)] (R = t-Bu) complexes with in idual bases of the above type. Comparative X-ray structural studies involving all ten base adduct derivatives have been obtained and reveal a range of interesting discrete and polymeric molecular architectures. The respective products have the following stoichiometries: [Cu(2)(L(1))(2)(Py)(2)].Py (R = Me), [Cu(2)(L(1))(2)(EtPy)(2)].2EtPy (R = t-Bu), [Cu(2)(L(1))(2)(pipi)(2)].2pipi (R = t-Bu), [Cu(2)(L(1))(2)(mmorph)(2)] (R = t-Bu), [Cu(2)(L(1))(2)(tmen)(2)] (R = t-Bu) and {[Cu(2)(L(1))(2)(pip)].pip.2THF}(n), [Co(2)(L(1))(2)(tmen)(2)] (R = t-Bu), [Ni(2)(L(1))(2)(Py)(4)].dmpip (R = t-Bu), [Ni(2)(L(1))(2)(pipi)(4)].pipi (R = t-Bu) and [Ni(2)(L(1))(2)(tmen)(2)] (R = t-Bu). The effect of pressure on the X-ray structure of [Cu(2)(L(1))(2)(mmorph)(2)] has been investigated. An increase in pressure from ambient to 9.1 kbar resulted in modest changes to the unit cell parameters as well as a corresponding decrease of 6.7 percent in the unit cell volume. While a small 'shearing' motion occurs between adjacent molecular units throughout the lattice, no existing bonds are broken or new bonds formed.
Synthesis, antifungal and antimicrobial activity of alkylphospholipids
Publisher: Elsevier BV
Date: 08-2007
DOI: 10.1016/J.BMC.2007.05.028
Abstract: The antifungal, antibacterial and haemolytic activity of a series of alkylphosphocholines (e.g., miltefosine) and alkylglycerophosphocholines (e.g., edelfosine) has been investigated. These compound classes exhibit significant antifungal and moderate antibacterial activities. Several new alkylphosphocholine derivatives with amide or ester bonds in the alkyl chain have been synthesised. These compounds show much lower haemolytic activity than miltefosine. Alkylphosphocholines and alkylglycerophosphocholines show significant promise as novel orally available antifungal and antibacterial therapeutics.
The nitration of some 4,6-dimethoxyindoles
Publisher: Elsevier BV
Date: 11-2004
A cyclooligomerisation approach to backbone-modified cyclic peptides bearing guanidinium arms
Publisher: Georg Thieme Verlag KG
Date: 22-12-2010
Selective Pyrophosphate Recognition by Cyclic Peptide Receptors in Physiological Saline
Publisher: Wiley
Date: 10-09-2012
Abstract: The anion binding ability of a family of bis(Zn II ‐Dpa) functionalized cyclic peptides has been investigated using displacement assays with a fluorescent coumarin indicator in water, saline solution, and Krebs buffer. Non‐binding side‐chain steric bulk, the relative position of binding sites, and the scaffold size were all found to affect the ability of these receptors to discriminate between polyphosphate ions. Most receptors showed some selectivity for pyrophosphate over ATP and ADP in water and saline, and this selectivity was significantly enhanced in the biologically relevant Krebs buffer giving chemosensing ensembles capable of selective recognition of pyrophosphate in the presence of excess ATP.
In vitro antifungal activities of bis(alkylpyridinium)alkane compounds against pathogenic yeasts and molds
Publisher: American Society for Microbiology
Date: 08-2010
DOI: 10.1128/AAC.00231-10
Abstract: Ten bis(alkylpyridinium)alkane compounds were tested for antifungal activity against 19 species (26 isolates) of yeasts and molds. We then determined the MICs and minimum fungicidal concentrations (MFCs) of four of the most active compounds (compounds 1, 4, 5, and 8) against 80 Candida and 20 cryptococcal isolates, in comparison with the MICs of hotericin B, fluconazole, itraconazole, voriconazole, posaconazole, and caspofungin, using Clinical Laboratory and Standards Institutes broth microdulition M27-A3 (yeasts) or M38-A2 (filamentous fungi) susceptibility protocols. The compounds were more potent against Candida and Cryptococcus spp. (MIC range, 0.74 to 27.9 μg/ml) than molds (0.74 to 59.7 μg/ml). MICs against Exophiala were 0.37 to 5.9 μg/ml and as low as 1.48 μg/ml for Scedosporium but ≥25 μg/ml for zygomycetes, Aspergillus , and Fusarium spp. Compounds 1, 4, 5, and 8 exhibited good fungicidal activity against Candida and Cryptococcus , except for Candida parapsilosis (MICs of μg/ml). Geometric mean (GM) MICs were similar to those of hotericin B and lower than or comparable to fluconazole GM MICs but 10- to 100-fold greater than those for the other azoles. GM MICs against Candida glabrata were μg/ml, significantly lower than fluconazole GM MICs ( P 0.001) and similar to those of itraconazole, posaconazole, and voriconazole (GM MIC range of 0.4 to 1.23 μg/ml). The GM MIC of compound 4 against Candida guilliermondii was lower than that of fluconazole (1.69 μg/ml versus 7.48 μg/ml P = 0.012). MICs against Cryptococcus neoformans and Cryptococcus gattii were similar to those of fluconazole. The GM MIC of compound 4 was significantly higher for C. neoformans (3.83 μg/ml versus 1.81 μg/ml for C. gattii P = 0.015). This study has identified clinically relevant in vitro antifungal activities of novel bisalkypyridinium alkane compounds.
Synthesis of dichotomin A: Use of a penicillamine-derived pseudoproline to furnish native valine residues
Publisher: CSIRO Publishing
Date: 2015
DOI: 10.1071/CH14569
Abstract: The total synthesis of cyclic hexapeptide dichotomin A from linear peptide precursors containing penicillamine-derived pseudoproline residues is reported. The incorporation of a pseudoproline residue led to a faster reaction and higher head-to-tail cyclization yields in comparison to linear precursors containing the native valine residue. However, deprotection of the pseudoproline resulted in significant amounts of a by-product in which a threonine side chain had undergone dehydration, resulting in a low overall yield of the natural product.
The electrochemical reduction of a flexible Mn(ii ) salen-based metal–organic framework
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1DT02589A
Abstract: A salen-based MOF is reported that is stable to desolvation and exhibits a crystalline-to-amorphous transition. The framework is stable to a one-electron reduction, which is characterised spectroelectrochemically and using computational calculations.
Synthesis of self-assembling cyclic peptide-polymer conjugates using click chemistry
Publisher: CSIRO Publishing
Date: 2010
DOI: 10.1071/CH10128
Abstract: Self-assembling cyclic peptide-polymer conjugates were prepared by ‘clicking’ polymers (prepared by RAFT polymerization) to an azide functionalized d-alt-l cyclic octapeptide via the Huisgen 1,3-dipolar cycloaddition reaction. Due to the high graft density, the efficiency of the click chemistry conjugation reaction was found to be highly dependent on the size of the polymer. At relatively low molecular weights, as many as four polymer chains could be grafted to each 8 residue cyclic peptide ring. Evidence for the self assembly of the conjugates into peptide-polymer nanotubes was observed by TEM and IR.
Interaction of copper(II) and palladium(II) with linked 2,2′-dipyridylamine derivatives: Synthetic and structural studies
Publisher: Elsevier BV
Date: 09-2008
Design and Synthesis of Two (Pseudo)symmetric Giant Trichromophoric Systems Containing the C60 Chromophore
Publisher: American Chemical Society (ACS)
Date: 28-01-1999
DOI: 10.1021/JO981940T
Hierarchical assembly of discrete copper(ii) metallo-structures from pre-assembled dinuclear (bis-β-diketonato)metallocycles and flexible difunctional co-ligands
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3DT51531A
Abstract: The sequential interaction of preformed [Cu2(L1)2(THF)2] (where H2L1 is 1,1-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione incorporating a 1,3-phenylene linker between its two β-diketone domains) and [Cu2(L4)2]·2H2O (where H2L4 is 1,1-(4,4′-oxybiphenylene)-bis(4,4-dimethylpentane-1,3-dione) incorporating a flexible oxybiphenylene linkage between the two β-diketone groups) with the potentially difunctional aliphatic non-planar co-ligands, N-methylpiperazine (mpip), N,N′-dimethylpiperazine (dmpip) and 1,4-thiomorpholine (thiomorph) is reported. A series of extended molecular assemblies exhibiting a range of di- and tetranuclear assemblies were obtained and their X-ray structures determined. Dinuclear [Cu2(L1)2(mpip)2]·2mpip incorporates two 5-coordinate, square pyramidal metal centres as does tetranuclear [{Cu2(L1)2}2(dmpip)2]·2dmpip. In contrast, dinuclear [Cu2(L1)2(dmpip)4]·dmpip and [{Cu2(L1)2}2(thiomorph)4]·3thiomorph each contain two 5-coordinate and two 6-coordinate centres. Each of [Cu2(L4)2(THF)2]·2THF and Cu2(L4)2(mpip)2]·H2O incorporate only 5-coordinate metal centres, with the latter complex forming a one-dimensional hydrogen bonded ribbon-like structure directed along the crystallographic a-axis. In keeping with the documented tendency for the smallest, least strained assembly to form in supramolecular self-assembly processes, the incorporation of the flexible “oxy” linkage between the 4,4′-linked phenylene rings of H2L3 results in generation of a dinuclear [Cu2L2] species rather than a trinuclear (triangular) [Cu3L3] species of the type formed by the more rigid bis-β-diketonato ligand analogue in which the biphenylene rings separating the β-diketone domains are directly coupled in their 4,4′ positions.
Hybrid cyclic peptide–thiourea cryptands for anion recognition
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0CC02223C
Abstract: Two cyclic peptide derived cryptands incorporating thioureas in the framework were synthesised as neutral anion receptors and bind acetate ions with high affinity and, in one case, good selectivity.
Synthesis of All-l Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers
Publisher: American Chemical Society (ACS)
Date: 21-06-2010
DOI: 10.1021/OL101018W
Abstract: Cyclic tetrapeptides have generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.
Synthesis of homogeneous antifreeze glycopeptides via a ligation–desulfurisation strategy
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B918021D
Abstract: Homogeneous glycopeptide analogues of fish antifreeze glycoproteins of discrete oligomeric length have been synthesised using a native chemical ligation-desulfurisation strategy.
Solid-State and Solution-Phase Conformations of Pseudoproline-Containing Dipeptides
Publisher: CSIRO Publishing
Date: 2009
DOI: 10.1071/CH09151
Abstract: The conformations of 14 threonine-derived pseudoproline-containing dipeptides (including four d-allo-Thr derivatives) have been investigated by NMR. In solution, the major conformer observed for all dipeptides is that in which the amide bond between the pseudoproline and the preceding amino acid is cis. For dipeptides in which the N-terminus is protected, the ratio of cis- to trans-conformers does not depend significantly on the side chain of the N-terminal amino acid, or the stereochemistry of the Thr residue. However, for dipeptides bearing a free N-terminus, there are significant differences in the ratios of cis- to trans-conformers depending on the side chain present. Three dipeptides were crystallized and their X-ray structures determined. In two cases, (benzyloxycarbonyl (Cbz)-Val-Thr(ΨMe,Mepro)-OMe and Cbz-Val-Thr(ΨMe,Mepro)-OH), the dipeptides adopt a trans-conformation in the solid state, in contrast to the structures observed in solution. In the third case, (9-fluorenylmethoxycarbonyl (Fmoc)-Val-d-allo-Thr(ΨMe,Mepro)-OH), a cis-amide geometry is observed. These structural differences are attributed to crystal-packing interactions.
Characterization of peptide immobilization on an acetylene terminated surface via click chemistry
Publisher: Elsevier BV
Date: 10-2011
Synthesis of N-linked glycopeptides via solid-phase aspartylation
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/C003673K
Abstract: An efficient strategy for the preparation of N-linked glycopeptides is described. The method relies on the use of side chain protecting groups on aspartic acid residues, namely the allyl and Dmab esters, which are orthogonal to those utilised in Fmoc-strategy SPPS. After peptide assembly these protecting groups were selectively removed and the resulting free side chains derivatised with a glycosylamine to afford a resin bound glycopeptide bearing a native N-linkage. Initially, N-linked glycopeptides were successfully synthesised according to this strategy, however, yields varied substantially depending on the nature of the amino acid residue situated adjacent (C-terminal) to the putative glycosylation site. This was due to generation of substantial quantities of aspartimide by-products. Aspartimide formation was overcome by incorporation of a 2,4-dimethoxybenzyl (Dmb) backbone amide protecting group on the residue adjacent to an allyl- or Dmab-protected aspartic acid residue. N-linked glycopeptides were prepared in excellent yield after the solid-phase aspartylation reactions. The utility and orthogonality of the allyl and Dmab ester solid-phase approaches were exploited in the preparation of an N-linked glycodecapeptide bearing two different carbohydrate moieties. This exemplified the efficiency of the solid-phase methodology for the preparation of glycopeptides bearing various combinations of N-linked glycans.
Cobalt(ii ), iron(ii ), zinc(ii ) and palladium(ii ) complexes of di-topic 4′-{4-[bis(2-pyridyl)aminomethyl]phenyl}-2,2′:6′,2′′-terpyridine. Synthetic and X-ray
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4CE00414K
Abstract: A new di-topic hybrid ligand incorporating terpy/dpa domains and the X-ray structures of five of its metal complexes are presented.
(1R,2S,3R,6S,7R,8S)-Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol
Publisher: International Union of Crystallography (IUCr)
Date: 06-12-2006
Diaminomethylenemalononitriles and Diaminomethyleneindanediones as Dual Hydrogen Bond Donors for Anion Recognition
Publisher: American Chemical Society (ACS)
Date: 23-03-2021
Deltamides and Croconamides: Expanding the Range of Dual H‐bond Donors for Selective Anion Recognition
Publisher: Wiley
Date: 15-12-2017
Abstract: Dual H-bond donors are widely used as recognition motifs in anion receptors. We report the synthesis of a library of dual H-bond receptors, incorporating the deltic and croconic acid derivatives, termed deltamides and croconamides, respectively, and a comparison of their anion binding affinities (for monovalent species) and Brønsted acidities to those of the well-established urea and squaramide dual H-bond donor motifs. For dual H-bonding cores with identical substituents, the trend in Brønsted acidity is croconamides>squaramides>deltamides>ureas, with the croconamides found to be 10-15 pK
Effect of the amino acid composition of cyclic peptides on their self-assembly in lipid bilayers
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4OB02041C
Abstract: The effect of amino acid composition on the formation of transmembrane channels in lipid bilayers upon self-assembly of alt-( l , d )-α-cyclic octapeptides has been investigated.
An expanded neutral M(4)L(6) cage that encapsulates four tetrahydrofuran molecules
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1CC11167A
Abstract: A large 4,4'-biphenylene-spaced bis-β-diketone ligand is demonstrated to form a neutral tetrahedral M(4)L(6) metal-organic cage that encloses a volume of 844 Å(3) and encapsulates four tetrahydrofuran guest molecules.
Total Synthesis of Microcin B17 via a Fragment Condensation Approach
Publisher: American Chemical Society (ACS)
Date: 14-01-2011
DOI: 10.1021/OL102916B
Abstract: The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.
Total synthesis and antiplasmodial activity of pohlianin C and analogues
Publisher: Elsevier BV
Date: 06-2014
DOI: 10.1016/J.BMCL.2014.04.071
Abstract: The first synthesis of the glycine-rich cyclic octapeptide pohlianin C is reported, confirming the structure of this natural product. Screening against Plasmodium falciparum reveals moderate antiplasmodial activity, consistent with data obtained from the natural s le. In addition, the synthesis of three analogues reveals that the antiplasmodial activity of pohlianin C can be preserved or increased with simplified structures.
Multi-shell soft nanotubes from cyclic peptide templates
Publisher: Wiley
Date: 03-01-2013
Interaction of an extended series of N-substituted di(2-picolyl)amine derivatives with copper(II). Synthetic, structural, magnetic and solution studies
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B901832H
Abstract: The interaction of Cu(II) with the following secondary N-substituted derivatives of di(2-picolyl)amine () are reported: N-cyclohexylmethyl-di(2-picolyl)amine (), N-benzyl-di(2-picolyl)amine (), N-(4-pyridylmethyl)-di(2-picolyl)amine (), N-(4-carboxymethylbenzyl)-di(2-picolyl)amine (), N-(9-anthracen-8-ylmethyl)-di(2-picolyl)amine (), 1,3-bis[di(2-picolyl)aminomethyl]benzene (), 1,4-bis[di(2-picolyl)aminomethyl]benzene () and 2,4,6-tris[di(2-picolyl)amino]triazine (). The solid complexes [Cu()(micro-Cl)](2)(PF(6))(2), [Cu()(micro-Cl)](2)(PF(6))(2).0.5CH(2)Cl(2), Cu()(ClO(4))(2), Cu()(2)(ClO(4))(2), [Cu()(ClO(4))(2)(H(2)O)].0.5H(2)O, Cu(2)()(ClO(4))(4), [Cu(2)()(Cl)(4)] and [Cu(2)(+H)(micro-OCH(3))(2)(H(2)O)](ClO(4))(3).C(4)H(10)O were isolated and X-ray structures of [Cu()(micro-Cl)](2)(PF(6))(2), [Cu()(micro-Cl)](2)(PF(6))(2).0.5CH(2)Cl(2,) [Cu()(2)(ClO(4))(2)(H(2)O)].0.5H(2)O, [Cu(2)()Cl(4)] and [Cu(2)(+H)(micro-OCH(3))(2)(H(2)O)](ClO(4))(3).C(4)H(10)O were obtained. The series is characterised by a varied range of coordination geometries and lattice architectures which in the case of [Cu()(ClO(4))(2)(H(2)O)].0.5H(2)O includes a chain-like structure formed by unusual intermolecular pi-interactions between metal bound perchlorate anions and the aromatic rings of adjacent anthracenyl groups. Variable temperature magnetic susceptibility measurements have been performed for [Cu()(micro-Cl)](2)(PF(6))(2) and [Cu()(micro-Cl)](2)(PF(6))(2).0.5H(2)O over the range 2-300 K. Both compounds show Curie-Weiss behaviour, with the data indicating weak antiferromagnetic interaction between the pairs of copper ions in each complex. Liquid-liquid (H(2)O/CHCl(3)) extraction experiments involving and as extractants showed that, relative to the parent (unsubstituted) dipic ligand , substitution at the secondary amine site in each case resulted in an increase in extraction efficiency towards Cu(II) (as its perchlorate salt) at least in part, this increase may be attributed to the enhanced lipophilicities of the N-substituted derivatives.
Tetraaquabis(pyridine-κN)cobalt(II) diacetate
Publisher: International Union of Crystallography (IUCr)
Date: 29-03-2006
DOI: 10.1107/S1600536806010257
Abstract: In the title complex, [Co(C 5 H 5 N) 2 (H 2 O) 4 ](C 2 H 3 O 2 ) 2 , the octahedral cation is hydrogen bonded to the acetate anions via the coordinated water molecules. The cation and anions lie on a crystallographic mirror plane.
Synthesis and Conformational Analysis of α,β‐Difluoro‐γ‐amino Acid Derivatives
Publisher: Wiley
Date: 20-01-2011
Noncovalent assembly of a fifteen-component hydrogen-bonded nanostructure
Publisher: Wiley
Date: 04-1999
DOI: 10.1002/(SICI)1521-3773(19990401)38:7<933::AID-ANIE933>3.0.CO;2-3
A Fluorescent Ditopic Rotaxane Ion‐Pair Host
Publisher: Wiley
Date: 05-03-2018
Abstract: We report a rotaxane based on a simple urea motif that binds Cl − selectively as a separated ion pair with H + and reports the anion binding event through a fluorescence switch‐on response. The host selectively binds Cl − over more basic anions, which deprotonate the framework, and less basic anions, which bind more weakly. The mechanical bond also imparts size selectivity to the ditopic host.
Tailoring the properties of a hypoxia-responsive 1,8-naphthalimide for imaging applications
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C7OB03164E
Abstract: A series of bioreductive fluorescent sensors based on nitro-naphthalimide enables matching of probe properties to biological application.
N,N-diethylaminosulfur trifluoride (DAST, Et2 NSF3 ) and related reagents
Publisher: CSIRO Publishing
Date: 2001
DOI: 10.1071/CH01030
Preparation of the Central Tryptophan Moiety of the Celogentin/Moroidin Family of Anti-Mitotic Cyclic Peptides
Publisher: CSIRO Publishing
Date: 2006
DOI: 10.1071/CH06324
Abstract: The central functionalized tryptophan core of the celogentin/moroidin family of cyclic peptides has been prepared. The strategy incorporates a novel preparation of 4-iodobenzaldehyde and employs a Larock annulation as the key step.
Selective sorption of actinides by titania nanoparticles covalently functionalized with simple organic ligands
Publisher: American Chemical Society (ACS)
Date: 18-11-2013
DOI: 10.1021/AM403727X
Abstract: Although current and proposed reprocessing of used nuclear fuel is performed predominantly by solvent extraction processes, solid phase sorbent materials have many advantages including the ability to avoid production of large volumes of organic waste. Therefore, three titania nanoparticle based sorbent materials have been developed, functionalized with organic ligands designed to impart selectivity for elements relevant to important separations at the back end of the nuclear fuel cycle. A novel, simplified method of covalent functionalization to the titania surface has been utilized, and the resulting materials have been shown to be hydrolytically stable at pH 2. The sorption behavior of these organofunctionalized titania materials was investigated over a wide pH range with a selection of elements including fission products and actinides. Titania nanoparticles functionalized with an amine or phosphate moiety were able to demonstrate exclusive extraction of uranium under optimized conditions. Titania nanoparticles functionalized with a picolinamide moiety exhibited superior minor actinide sorption properties, in terms of both efficiency and selectivity, to solvent extraction processes using similar organic moieties. As such, organo-functionalized titania materials as solid phase sorbents show promise as a future alternative to solvent extraction processes for nuclear separations.
Synthesis of Nitro‐Aryl Functionalised 4‐Amino‐1,8‐Naphthalimides and Their Evaluation as Fluorescent Hypoxia Sensors
Publisher: Wiley
Date: 29-06-2020
A comparison of pseudoproline substitution effects on cyclisation yield in the total syntheses of segetalins B and G
Publisher: Wiley
Date: 23-02-2018
DOI: 10.1002/PEP2.24042
Cyclic peptide–polymer conjugates: Grafting‐to vs grafting‐from
Publisher: Wiley
Date: 20-10-2015
DOI: 10.1002/POLA.27937
Anion recognition by cyclic peptides
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CC10095F
Abstract: Cyclic peptides provide excellent scaffolds for anion recognition and improved binding affinity and selectivity has been achieved through peptide backbone rigidification and the introduction of side chains bearing anion recognition groups.
Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi
Publisher: Royal Society of Chemistry (RSC)
Date: 19-12-2003
DOI: 10.1039/B209992F
Abstract: The title alkaloid 1 and its B-nor-congener 3, both of which display potent and unusual anti-mitotic properties, have been synthesized in racemic form and characterised by single-crystal X-ray analysis.
Miltefosine induces apoptosis-like cell death in yeast via Cox9p in cytochrome c oxidase
Publisher: American Society for Pharmacology & Experimental Therapeutics (ASPET)
Date: 24-05-2011
Abstract: Miltefosine has antifungal properties and potential for development as a therapeutic for invasive fungal infections. However, its mode of action in fungi is poorly understood. We demonstrate that miltefosine is rapidly incorporated into yeast, where it penetrates the mitochondrial inner membrane, disrupting mitochondrial membrane potential and leading to an apoptosis-like cell death. COX9, which encodes subunit VIIa of the cytochrome c oxidase (COX) complex in the electron transport chain of the mitochondrial membrane, was identified as a potential target of miltefosine from a genomic library screen of the model yeast Saccharomyces cerevisiae. When overexpressed in S. cerevisiae, COX9, but not COX7 or COX8, led to a miltefosine-resistant phenotype. The effect of miltefosine on COX activity was assessed in cells expressing different levels of COX9. Miltefosine inhibited COX activity in a dose-dependent manner in Cox9p-positive cells. This inhibition most likely contributed to the miltefosine-induced apoptosis-like cell death.
Fluorescent and colorimetric chemosensors for pyrophosphate
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CS00353E
Abstract: In this review, we will cover the fluorescent and colorimetric chemosensors developed for the detection of pyrophosphate (PPi) since 2010.
Receptors for sulfate that function across a wide pH range in mixed aqueous–DMSO media
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CC06812K
Abstract: Water soluble macrocyclic squaramides bind selectively to sulfate in aqueous–DMSO mixtures across a pH range from 3.2–14.
The impact of structural variation in simple lanthanide binding peptides
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6RA12880G
Abstract: A series of di-, tri- and tetra-peptides were synthesised using l - and d -glutamic acid in order to determine the effects of peptide length and stereochemistry on lanthanide binding affinity.
Hierarchical assembly of branched supramolecular polymers from (cyclic peptide)-polymer conjugates
Publisher: American Chemical Society (ACS)
Date: 14-10-2014
DOI: 10.1021/BM501062D
Abstract: We report the synthesis and assembly of (N-methylated cyclic peptide)-polymer conjugates for which the cyclic peptide is attached to either the α- or both α- and ω- end groups of a polymer. A combination of chromatographic, spectroscopic, and scattering techniques reveals that the assembly of the conjugates follows a two-level hierarchy, initially driven by H-bond formation between two N-methylated cyclic peptides, followed by unspecific, noncovalent aggregation of this peptide into small domains that behave as branching points and lead to the formation of branched supramolecular polymers.
Total Synthesis of Cyclocitropside A and Its Conversion to Cyclocitropsides B and C via Asparagine Deamidation
Publisher: American Chemical Society (ACS)
Date: 19-09-2012
DOI: 10.1021/OL3023853
Abstract: The total syntheses of three closely related cyclic peptide natural products, cyclocitropsides A-C, are described. Cyclocitropside A could be readily converted into cyclocitropsides B and C through an asparagine deamidation pathway, indicating that this is a plausible biosynthetic route to these compounds.
Effective Am(iii)/Eu(iii) separations using 2,6-bis(1,2,4-triazin-3-yl)pyridine (BTP) functionalised titania particles and hierarchically porous beads
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CC03957F
Abstract: Titania particles and beads functionalised with a modified BTP ligand have been used to selectively extract Am( iii ) over Eu( iii ) from 0.01 M nitric acid solutions.
Self-assembling macromolecular chimeras: Controlling fibrillization of a β-sheet forming peptide by polymer conjugation
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0SM01237H
Synthetic strategies for the design of peptide/polymer conjugates
Publisher: Informa UK Limited
Date: 22-04-2011
Backbone-modified cyclic peptides: New scaffolds for supramolecular chemistry
Publisher: Informa UK Limited
Date: 2005
Self-Assembly of Rodlike Hydrogen-Bonded Nanostructures
Publisher: American Chemical Society (ACS)
Date: 14-07-1999
DOI: 10.1021/JA9905344
The spectroelectrochemical behaviour of redox-active manganese salen complexes
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8DT02676A
Abstract: A series of discrete, functionalised Mn( iii ) pyridyl salen metal complexes with varying aliphatic and aromatic bridging diamines have been evaluated and their spectroelectrochemical properties probed.
Tuning colourimetric indicator displacement assays for naked-eye sensing of pyrophosphate in aqueous media
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3SC22233K
Quantum Chemical Prediction of Equilibrium Acidities of Ureas, Deltamides, Squaramides, and Croconamides
Publisher: American Chemical Society (ACS)
Date: 11-09-2017
Abstract: Robust quantum chemical methods are employed to predict the pK
Synthesis of the Side Chain Cross-Linked Tyrosine Oligomers Dityrosine, Trityrosine, and Pulcherosine
Publisher: American Chemical Society (ACS)
Date: 10-08-2005
DOI: 10.1021/JO051076M
Abstract: [reaction: see text] An efficient synthesis of dityrosine and the first syntheses of the tyrosine trimers trityrosine and pulcherosine have been achieved. Protected 3-iodotyrosine underwent tandem Miyaura borylation-Suzuki coupling to give protected dityrosine. The choice of benzyl carbamate, ester, and ether protecting groups enabled a one-step global deprotection to give dityrosine. Suzuki coupling of protected 3,5-diiodotyrosine and tyrosine-3-boronic acid derivatives gave the corresponding trityrosine, but in low yield. However, use of a potassium tyrosine-3-trifluoroborate derivative in place of the corresponding pinacol boronate ester, in combination with protecting group variation, gave protected trityrosine in good yield. Access to pulcherosine was achieved through copper-catalyzed coupling of phenylalanine-4-boronic acid and 4-O-protected dopa derivatives to give an isodityrosine derivative. Selective halogenation followed by Suzuki coupling with the potassium tyrosine-3-trifluoroborate gave protected pulcherosine. Global deprotection of the protected trityrosine and pulcherosine derivatives completed the first syntheses of the corresponding tris-alpha-amino acids.
Synthesis and Evaluation of a Series of Bis(pentylpyridinium) Compounds as Antifungal Agents
Publisher: Wiley
Date: 19-06-2018
Abstract: A series of bis(4-pentylpyridinium) compounds with a variety of spacers between the pyridinium headgroups was synthesised, and the antifungal activity of these compounds was investigated. Lengthening the alkyl spacer between the pentylpyridinium headgroups from 12 to 16 methylene units resulted in increased antifungal activity against C. neoformans and C. albicans, but also resulted in increased hemolytic activity and cytotoxicity against mammalian cells. However, inclusion of an ortho-substituted benzene ring in the centre of the alkyl spacer resulted in decreased cytotoxicity and hemolytic activity, while maintaining antifungal potency. Replacement of the alkyl and aromatic-containing spacers by more hydrophilic ethylene glycol groups resulted in a loss of antifungal activity. Some of the compounds inhibited fungal PLB1 activity, but the low correlation of this inhibition with antifungal potency indicates PLB1 inhibition is unlikely to be the predominant mode of antifungal action of this class of compounds, with preliminary studies suggesting they may act via disruption of fungal mitochondrial function.
Characterization of hydrogen-bonded supra-molecular assemblies by MALDI-TOF mass spectrometry after Ag+ labeling
Publisher: Wiley
Date: 18-05-1998
DOI: 10.1002/(SICI)1521-3773(19980518)37:9<1247::AID-ANIE1247>3.0.CO;2-7
Synthesis of a family of cyclic peptide-based anion receptors
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C0OB01072C
Abstract: We report here the design and synthesis of a family of novel backbone modified cyclic peptides, bearing dipicolylamine side chains for metal complexation and subsequent anion binding studies. Two approaches to the cyclic peptides were investigated. Initially, a stepwise approach was employed, involving solid-phase assembly of oxazole-based building blocks, followed by solution-phase macrolactamisation of the resulting linear precursor. The alternative strategy involved the formation of linear bisoxazole fragments in solution-phase, followed by a cyclodimerisation reaction. The zinc(II) complexes of these receptors bind selectively to di- and tri-phosphate ions over hydrogenphosphate.
Conformational and photophysical studies on porphyrin-containing donor–bridge–acceptor compounds. Charge separation in micellar nanoreactors
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B511157A
Abstract: Photophysical studies with semi-rigid, 1, and flexible, 2, donor-bridge-acceptor (D-b-A2+) molecules with D a porphyrin and A2+ a methyl viologen moiety, were performed in neat polar solvents as well as included in surfactant (DTAB) aqueous and in reverse AOT/n-alkane micelles. The micelles acted as nanoreactors for the photoinduced electron transfer reaction upon laser excitation. In spite of the longer lifetime of the charge separated (CS) state in the semi-rigid tetrad 1(ca. 200 ns vs. ca. 100 ns for the flexible dyad 2), the CS formation quantum yield, for ex le in acetonitrile, was lower for the former (phi(CS) = 0.13) than for the latter (0.58). Comparison of the time-resolved fluorescence data in neat solvent and in the micelles yielded the phi(CS) values in the dilute micellar solutions. Application of laser-induced optoacoustic spectroscopy at various temperatures to 1 dissolved in a polar organic solvent (benzonitrile, BZN) included in aqueous DTAB nanoreactors afforded structural volume changes for the production in hundreds of ps of the CS state upon excitation of a polar molecule. The contraction during CS formation upon excitation of the collapsed conformer in BZN is attributed to the entering of solvent into the open molecular cavity. The opening upon formation of the CS state due to photoinduced electron transfer in the 1 collapsed conformation arises from the repulsion of the two positively charged ends in this state, as previously calculated. Inclusion of 1 in reverse AOT micelles in various n-alkanes also led to a contraction upon excitation, but the data had much more error due to the limited range of variability of the ratio of thermoelastic parameters. The data obtained with the more flexible "supermolecule" 2 showed the predicted large conformation flexibility of these molecules.
A Fluorescent Ditopic Rotaxane Ion‐Pair Host
Publisher: Wiley
Date: 05-03-2018
Polymer-peptide chimeras for the multivalent display of immunogenic peptides
Publisher: Royal Society of Chemistry (RSC)
Date: 2010
DOI: 10.1039/B924112D
Abstract: Chimeras of poly(n-isopropyl acrylamide) and immunogenic peptides from the cancer-associated glycoprotein MUC1 were synthesised using a combination of solid-phase peptide synthesis, RAFT polymerisation and copper-catalysed alkyne-azide cycloaddition reactions.
Investigating the effects of structure on sulfate recognition by neutral dipeptide receptors
Publisher: Informa UK Limited
Date: 29-01-2018
A chemoenzymatic synthesis of (−)-hirsutene from toluene
Publisher: Royal Society of Chemistry (RSC)
Date: 2002
DOI: 10.1039/B208778B
Liquid–liquid extraction studies with 4,4′-biphenylene-spaced bis-β-diketones
Publisher: Springer Science and Business Media LLC
Date: 27-04-2011
N,O-Isopropylidenated Threonines as Tools for Peptide Cyclization: Application to the Synthesis of Mahafacyclin B
Publisher: American Chemical Society (ACS)
Date: 29-10-2005
DOI: 10.1021/OL0522891
Abstract: [structure: see text] The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.
Structure elucidation and control of cyclic peptide-derived nanotube assemblies in solution
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3SC00064H
A new nickel(II) coordination polymer derived from [Ni(N,N-ethylenebis(1,1,1-trifluoroacetylacetoneiminato)] and 1,4-diazabicyclo[2.2.2]octane
Publisher: Elsevier BV
Date: 04-2010
Secondary Self-Assembly of Supramolecular Nanotubes into Tubisomes and Their Activity on Cells
Publisher: Wiley
Date: 21-11-2018
Abstract: The properties and structures of viruses are directly related to the three-dimensional structure of their capsid proteins, which arises from a combination of hydrophobic and supramolecular interactions, such as hydrogen bonds. The design of synthetic materials demonstrating similar synergistic interactions still remains a challenge. Herein, we report the synthesis of a polymer/cyclic peptide conjugate that combines the capability to form supramolecular nanotubes via hydrogen bonds with the properties of an hiphilic block copolymer. The analysis of aqueous solutions by scattering and imaging techniques revealed a barrel-shaped alignment of single peptide nanotubes into a large tubisome (length: 260 nm (from SANS)) with a hydrophobic core (diameter: 16 nm) and a hydrophilic shell. These systems, which have a structure that is similar to those of viruses, were tested in vitro to elucidate their activity on cells. Remarkably, the rigid tubisomes are able to perforate the lysosomal membrane in cells and release a small molecule into the cytosol.
A Fluorogenic Probe for Cell Surface Phosphatidylserine Using an Intramolecular Indicator Displacement Sensing Mechanism
Publisher: Wiley
Date: 13-12-2018
Abstract: The detection of externalized phosphatidylserine (PS) on the cell surface is commonly used to distinguish between living, apoptotic, and necrotic cells. The tools of choice for many researchers to study apoptosis are annexin V-fluorophore conjugates. However, the use of this 35 kDa protein is associated with several drawbacks, including temperature sensitivity, Ca
Correlation of antifungal activity with fungal phospholipase inhibition using a series of bisquaternary ammonium salts
Publisher: American Chemical Society (ACS)
Date: 16-12-2006
DOI: 10.1021/JM0508843
Abstract: A series of bisquaternary ammonium salts with a 12-carbon spacer between the positive charges were synthesized, and their antifungal activity has been investigated. Compounds with butyl, pentyl, and isopentyl headgroups were the most potent antifungal agents with MICs in the range of 2.2-5.5 microM against both Cryptococcus neoformans and Candida albicans. The antifungal activity of these compounds correlated with their inhibition of cryptococcal phospholipase B1 (PLB1), a newly identified virulence factor. This indicates that the mode of action of these compounds may be inhibition of the fungal PLB1 enzyme, further validating this enzyme as a target for the development of novel antifungal therapies.
Thiosquaramides: PH switchable anion transporters
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4SC01629G
Abstract: Thiosquaramides show pH controlled anion transport properties in lipid bilayers.
Cyclic Peptide-Polymer Nanotubes as Efficient and Highly Potent Drug Delivery Systems for Organometallic Anticancer Complexes
Publisher: American Chemical Society (ACS)
Date: 14-12-2018
DOI: 10.1021/ACS.BIOMAC.7B01491
Abstract: Functional drug carrier systems have potential for increasing solubility and potency of drugs while reducing side effects. Complex polymeric materials, particularly anisotropic structures, are especially attractive due to their long circulation times. Here, we have conjugated cyclic peptides to the biocompatible polymer poly(2-hydroxypropyl methacrylamide) (pHPMA). The resulting conjugates were functionalized with organoiridium anticancer complexes. Small angle neutron scattering and static light scattering confirmed their self-assembly and elongated cylindrical shape. Drug-loaded nanotubes exhibited more potent antiproliferative activity toward human cancer cells than either free drug or the drug-loaded polymers, while the nanotubes themselves were nontoxic. Cellular accumulation studies revealed that the increased potency of the conjugate appears to be related to a more efficient mode of action rather than a higher cellular accumulation of iridium.
Cyclic peptide-poly(HPMA) nanotubes as drug delivery vectors: In vitro assessment, pharmacokinetics and biodistribution
Publisher: Elsevier BV
Date: 09-2018
DOI: 10.1016/J.BIOMATERIALS.2018.03.047
Abstract: Size and shape have progressively appeared as some of the key factors influencing the properties of nanosized drug delivery systems. In particular, elongated materials are thought to interact differently with cells and therefore may allow alterations of in vivo fate without changes in chemical composition. A challenge, however, remains the creation of stable self-assembled materials with anisotropic shape for delivery applications that still feature the ability to disassemble, avoiding organ accumulation and facilitating clearance from the system. In this context, we report on cyclic peptide-polymer conjugates that self-assemble into supramolecular nanotubes, as confirmed by SANS and SLS. Their behaviour ex and in vivo was studied: the nanostructures are non-toxic up to a concentration of 0.5 g L
Molecular recognition and sensing of dicarboxylates and dicarboxylic acids
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0OB01761B
Abstract: This review outlines challenges faced in recognition and detection of dicarboxylic acids and dicarboxylates and strategies used to obtain effective and observable interactions in the period from 2014 to 2020.
Selective Anion Binding in Water with Use of a Zinc(II) Dipicolylamino Functionalized Diketopiperazine Scaffold
Publisher: American Chemical Society (ACS)
Date: 17-03-2009
DOI: 10.1021/JO802555U
Abstract: The design and synthesis of a diketopiperazine based anion receptor bearing two dipicolylamino arms complexed to zinc(II) ions is described. This receptor is readily prepared from the dipeptide precursor by a microwave-assisted intramolecular cyclization reaction. Upon addition of zinc(II), the receptor binds di- and triphosphate ions with high affinity and selectivity in aqueous solution, as determined by using a fluorescent indicator displacement assay.
Are two better than one? Comparing intermolecular and intramolecular indicator displacement assays in pyrophosphate sensors
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6CC03680E
Abstract: Pyrophosphate recognition using indicator displacement assays is compared to that of analogous receptors with covalently attached indicators.
π-Allyl cation cyclisations initiated by electrocyclic ring-opening of gem-dihalocyclopropanes: application to the first total syntheses of the crinine-type alkaloids maritinamine and epi-maritinamine
Publisher: Royal Society of Chemistry (RSC)
Date: 2001
DOI: 10.1039/B106369N
Synthesis of sansalvamide A peptidomimetics: triazole, oxazole, thiazole, and pseudoproline containing compounds
Publisher: Elsevier BV
Date: 2012
Shaping block copolymer micelles by supramolecular polymerization: Making 'tubisomes'
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9PY00179D
Abstract: In contrast to the respective block copolymers, hiphilic cyclic peptide conjugates self-assemble into cylindrical micelles independent of the polymer compositions.
Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors
Publisher: Walter de Gruyter GmbH
Date: 2003
Abstract: The enantiomerically pure cis -1,2-dihydrocatechols 2 , which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain ex les of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (−)-patchoulenone and (−)-hirsutene.
Study of (Cyclic Peptide)–Polymer Conjugate Assemblies by Small-Angle Neutron Scattering
Publisher: Wiley
Date: 10-11-2016
Abstract: We present a fundamental study into the self-assembly of (cyclic peptide)-polymer conjugates as a versatile supramolecular motif to engineer nanotubes with defined structure and dimensions, as characterised in solution using small-angle neutron scattering (SANS). This work demonstrates the ability of the grafted polymer to stabilise and/or promote the formation of unaggregated nanotubes by the direct comparison to the unconjugated cyclic peptide precursor. This ideal case permitted a further study into the growth mechanism of self-assembling cyclic peptides, allowing an estimation of the cooperativity. Furthermore, we show the dependency of the nanostructure on the polymer and peptide chemical functionality in solvent mixtures that vary in the ability to compete with the intermolecular associations between cyclic peptides and ability to solvate the polymer shell.
Selective sensing of pyrophosphate in physiological media using zinc(ii )dipicolylamino-functionalised peptides
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5OB00956A
Abstract: Linear zinc( ii )dipicolylamino-functionalised peptides show high affinity and selectivity for pyrophosphate in physiological media.
Conformationally adaptable macrocyclic receptors for ditopic anions: analysis of chelate cooperativity in aqueous containing media
Publisher: Royal Society of Chemistry (RSC)
Date: 2020
DOI: 10.1039/D0SC02533J
Abstract: Chelate cooperativity impacts the binding affinities of dicarboxylates of different sizes to flexible thiourea macrocycles in aqueous DMSO.
Remarkable Conformational Control of Photoinduced Charge Separation and Recombination in a Giant U-Shaped Tetrad
Publisher: American Chemical Society (ACS)
Date: 18-10-2000
DOI: 10.1021/JA001492I
Luminescent probes for the bioimaging of small anionic species in vitro and in vivo
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C4CS00372A
Abstract: This comprehensive review examines recent developments in the use of fluorescent/luminescent probes for the bioimaging of anionic species. Images in cover art reproduced with permission from ref. 290 and 306.
Thermal gating in lipid membranes using thermoresponsive cyclic peptide-polymer conjugates
Publisher: American Chemical Society (ACS)
Date: 21-05-2014
DOI: 10.1021/JA5024699
Abstract: The partition and self-assembly of a new generation of cyclic peptide-polymer conjugates into well-defined phospholipid trans-bilayer channels is presented. By varying the structural parameters of the cyclic peptide-polymer conjugates through the ligation of hydrophobic and hydrophilic polymers, both the structure of the artificial channels using large unilamellar vesicle assays and the structural parameters required for phospholipid bilayer partitioning are elucidated. In addition, temperature was used as an external stimulus for the modulation of transbilayer channel formation without requiring the redesign and synthesis of the cyclic peptide core. The thermoresponsive character of the cyclic peptide-polymer conjugates lays the foundation for on-demand control over phospholipid transmembrane transport, which could lead to viable alternatives to current transport systems that traditionally rely on endocytic pathways.
Nickel(II) and zinc(II) complexes of N-substituted di(2-picolyl)amine derivatives: Synthetic and structural studies
Publisher: Elsevier BV
Date: 03-2011
Synthesis of 7-indolyl-imines by the reaction of 4,6-dimethoxyindoles with secondary amides and phosphoryl chloride
Publisher: Elsevier BV
Date: 03-1996
Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer
Publisher: American Chemical Society (ACS)
Date: 30-07-2003
DOI: 10.1021/JO034689C
Abstract: (-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.
Thermoresponsive cyclic peptide – poly(2-ethyl-2-oxazoline) conjugate nanotubes
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/C3CC42327A
Abstract: We describe the synthesis of self-assembling cyclic octapeptides of alternating D- and L-chirality conjugated to two poly(2-ethyl-2-oxazoline) chains. The resulting conjugates form nanotubes in water, which are reversibly transformed into microparticles as the temperature reaches the cloud point temperature of the conjugate.
Efficient use of the Dmab protecting group: applications for the solid-phase synthesis of N-linked glycopeptides
Publisher: Royal Society of Chemistry (RSC)
Date: 2009
DOI: 10.1039/B821051A
Abstract: An efficient protocol for the chemoselective removal of Dmab esters on the solid phase is reported this method has been successfully utilised for the convergent solid phase synthesis of N-linked glycopeptides.
Synthetic peptides with selective affinity for apoptotic cells
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B514748D
Abstract: The appearance of anionic phosphatidylserine (PS) in the outer monolayer of the plasma membrane is a universal indicator of the early/intermediate stages of cell apoptosis. The most common method of detecting PS on a cell surface is to use the protein annexin V however, in certain applications there is a need for alternative reagents. Recent research indicates that rationally designed zinc 2,2'-dipicolylamine (Zn2+-DPA) coordination complexes can mimic the apoptosis sensing function of annexin V. Here, a series of fluorescently-labelled, tri- and pentapeptides with side chains containing Zn2+-DPA are prepared and shown to selectively bind to anionic vesicle membranes. Fluorescein-labelled versions of the peptides are used to detect apoptotic cells by fluorescence microscopy and flow cytometry.
A colorimetric sensor array for the classification of biologically relevant tri-, di- and mono-phosphates
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0OB02397C
Abstract: A cyclic tetrapeptide paired with six commercially available indicators provides a chemosensing array able to classify biological phosphate derivatives.
Bis[squaramido]ferrocenes as electrochemical sulfate receptors
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2NJ03951F
Abstract: The bis[squaramido]ferrocene scaffold is introduced and shown to selectively bind and electrochemically report sulfate in competitive water/DMSO mixtures.
Selective recognition of sulfate ions by tripodal cyclic peptides functionalised with (thio)urea binding sites
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2OB06964D
Abstract: A tripodal urea and tripodal thiourea with the same cyclic peptide core have been synthesised and their anion binding ability investigated. In CDCl(3), the tripodal urea self-associates whereas the thiourea does not. Neither compound shows self-association in the more polar 10% v/v DMSO-d(6)/CDCl(3). Both compounds bind strongly and selectively to sulfate ions in CDCl(3) and 10% v/v DMSO-d(6)/CDCl(3). This selectivity is attributed to a unique binding mode for sulfate, in which this tetrahedral anion forms nine hydrogen bonds to the receptors, with three of these coming from the amide protons of the cyclic peptide.
Anion recognition and sensing with Zn(II)–dipicolylamine complexes
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CS35087D
Abstract: This critical review covers the developments in anion recognition and sensing using Zn(II)-dipicolylamine functionalized receptors over the past decade with emphasis on recent rapid advances in the last five years.
Design and properties of functional nanotubes from the self-assembly of cyclic peptide templates
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2CS35172B
Abstract: β-Sheet forming self assembling cyclic peptides offer a versatile scaffold for the construction and control of hydrogen-bonded nanotube assemblies. These structures have major advantages over other nanoscale tubular structures, including sub-nanometer control over the internal diameter, and the ability to control internal and external chemical functionality. This Tutorial Review presents an overview of nanotubes derived from this class of cyclic peptides. The design rationale for functional nanotubes based on cyclic peptide ring size and chemical functionality is discussed. Additionally, we highlight the recent expansion of the nanotube toolbox through conjugation of (macro)molecules to the cyclic peptides. These provide additional functionality and control nanotube dimensions that could potentially prove beneficial in future applications.
Selective Removal of Sulfate from Water by Precipitation with a Rigid Bis‐amidinium Compound
Publisher: Wiley
Date: 14-02-2023
Abstract: A simple, readily prepared biphenyl bis‐amidinium compound ( 1⋅Cl 2 ) is able to selectively precipitate sulfate from water. The precipitant is effective at concentrations as low as 1 mM and shows complete selectivity against monovalent anions, and high selectivity even against CO 3 2− and HPO 4 2− . It is highly effective ( % sulfate removed) in both seawater and highly acidic conditions relevant to mining waste‐streams. X‐ray crystallography reveals that 1⋅SO 4 forms a tightly packed, anhydrous, structure where each sulfate anion receives eight hydrogen bonds from amidinium N−H hydrogen bond donors.
Neutral (bis-β-diketonato) iron(iii ), cobalt(ii ), nickel(ii ), copper(ii ) and zinc(ii ) metallocycles: structural, electrochemical and solvent extr
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B701575E
Abstract: Neutral dimeric metallocyclic complexes of type [M(2)(L(1))(2)B(n)] (where M = cobalt(II), nickel(II) and zinc(II), L(1) is the doubly deprotonated form of a 1,3-aryl linked bis-beta-diketone ligand of type 1,3-bis(RC(O)CH(2)C(O))C(6)H(4) (R=Me, n-Pr, t-Bu) and B is pyridine (Py) or 4-ethylpyridine (EtPy)) have been synthesised, adding to similar complexes already reported for copper(II). New lipophilic ligand derivatives with R = octyl or nonyl were also prepared for use in solvent extraction experiments. Structural, electrochemical and solvent extraction investigations of selected metal complex systems from the above series are reported, with the X-ray structures of [Co(2)(L(1))(2)(Py)(4)] x 2.25CHCl(3) x 0.5H(2)O (R=Pr), [Co(2)(L(1))(2)(EtPy)(4)] (R=t-Bu), [Ni(2)(L(1))(2)(EtPy)(4)] (R=t-Bu), [Zn(2)(L(1))(2)(EtPy)(2)] (R=Me) and [Zn(2)(L(1))(2)(EtPy)(4)] (R=t-Bu) being presented. The electrochemistry of H(2)L(1) (R=t-Bu) and of [Fe(2)(L(1))(3)], [Co(2)(L(1))(2)(Py)(4)], [Ni(2)(L(1))(2)(Py)(4)], [Cu(2)(L(1))(2)] and [Zn(2)(L(1))(2)(Py)(2)] has been examined. Oxidative processes for the complexes are dominantly irreversible, but several ex les of quasireversible behaviour were observed and support the assignment of an anodic process, seen between +1.0 and +1.6 V, as a metal-centred oxidation. The reduction processes for the respective metal complexes are not simple, and irreversible in most cases. Solvent extraction studies (water/chloroform) involving variable concentrations of metal, bis-beta-diketone and heterocyclic base have been performed for cobalt(II) and zinc(II) using a radiotracer technique to probe the stoichiometries of the extracted species in each case. Synergism was observed when 4-ethylpyridine was added to the bis-beta-diketone ligand in the chloroform phase. Competitive extraction studies show a clear uptake preference for copper(II) over cobalt(II), nickel(II), zinc(II) and cadmium(II).
Drug conjugation to cyclic peptide-polymer self-assembling nanotubes
Publisher: Wiley
Date: 21-08-2014
Abstract: We show for the first time how polymeric nanotubes (NTs) based on self-assembled conjugates of polymers and cyclic peptides can be used as an efficient drug carrier. RAPTA-C, a ruthenium-based anticancer drug, was conjugated to a statistical co-polymer based on poly(2-hydroxyethyl acrylate) (pHEA) and poly(2-chloroethyl methacrylate) (pCEMA), which formed the shell of the NTs. Self-assembly into nanotubes (length 200-500 nm) led to structures exhibiting high activity against cancer cells.
The Pseudoproline Approach to Peptide Cyclization
Publisher: CSIRO Publishing
Date: 2018
DOI: 10.1071/CH18292
Abstract: The development of efficient methods for the synthesis of cyclic peptides is of interest because of the many potential applications of this class of molecule. Pseudoprolines are derived from serine, threonine, and cysteine and can be used as traceless turn-inducers to facilitate the cyclization of a wide range of linear peptide precursors. The incorporation of a pseudoproline into the peptide to be cyclized generally results in a cyclization reaction that proceeds more quickly and with higher yield than that of an analogous sequence without the pseudoproline. Installation of a pseudoproline at the C-terminal position of a linear peptide sequence has also been shown to eliminate any epimerization of this residue during the reaction. Following pseudoproline-mediated cyclization, these turn-inducers can be removed on treatment with acid in a similar manner to other protecting groups to provide the native peptide sequence, and in the case of cysteine-derived pseudoprolines, the resulting cysteine can be readily converted into alanine through desulfurization. These traceless turn-inducers have been successfully used in the synthesis of cyclic peptides containing either serine, threonine, cysteine or alanine residues.
Chemoselective Peptide Ligation–Desulfurization at Aspartate
Publisher: Wiley
Date: 24-07-2013
A chemoenzymatic synthesis of the linear triquinane (-)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer
Publisher: Elsevier BV
Date: 2004
Synthesis of tris-(azacrown) ethers for carboxylic acid recognition
Publisher: Elsevier BV
Date: 2013
Supramolecular chemistry: defined. A personal perspective
Publisher: Informa UK Limited
Date: 31-05-2017
pH switchable anion transport by an oxothiosquaramide
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CC03625A
Abstract: An oxothiosquaramide was shown to bind to chloride through hydrogen bonding interactions in DMSO and found to exhibit pH switchable chloride transport across phospholipid bilayers via an antiport transport mechanism.
A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues
Publisher: Beilstein Institut
Date: 21-08-2012
DOI: 10.3762/BJOC.8.154
Abstract: The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey–Nicolaou) resulted in significant epimerization of the C -terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.
Molecular capsules and coordination polymers from a backbone-modified cyclic peptide bearing pyridyl arms
Publisher: Informa UK Limited
Date: 20-06-2012
An Area‐Specific, International Community‐Led Approach to Understanding and Addressing Equality, Diversity, and Inclusion Issues within Supramolecular Chemistry
Publisher: Wiley
Date: 08-03-2021
Abstract: Diversity, equality, and inclusion (DEI/EDI) are pressing issues in chemistry and the natural sciences. In this Essay we share how an area‐specific approach is “calling in” the community so that it can act to address EDI issues, and support those who are marginalised. Women In Supramolecular Chemistry (WISC) is an international network that aims to support equality, ersity, and inclusion within supramolecular chemistry. WISC has taken a field‐specific approach using qualitative research methods with scientists to identify the support that is needed and the problems the supramolecular community needs to address. Herein, we present survey data from the community which highlight the barriers that are faced by those who take career breaks for any reason, a common ex le is maternity leave, and the importance of mentoring to aid progression post‐PhD. In conclusion, we set out an interdisciplinary and creative approach to addressing EDI issues within supramolecular chemistry.
Functional characterization of the hexose transporter Hxt13p: An efflux pump that mediates resistance to miltefosine in yeast
Publisher: Elsevier BV
Date: 12-2013
DOI: 10.1016/J.FGB.2013.09.005
Abstract: Miltefosine (MI) has in vitro fungicidal activity against pathogenic fungi. However, mechanisms of resistance to MI have not been studied. By screening a genomic library of the model yeast, Saccharomyces cerevisiae, we identified HXT13 as a candidate genetic determinant of MI resistance. HXT13 belongs to the yeast hexose transporter family, which mediates hexose sugar uptake and is included in the major facilitator superfamily (MFS). We now report that overexpression of HXT13, but not of the closely-related genes, HXT15 and HXT17, and the more distantly related HXT14, resulted in a stable MI-resistant phenotype in S. cerevisiae. Resistance of the HXT13 overexpressing strain to MI correlated with higher cell viability following MI exposure as assessed by SYTOX® green staining compared with the control and overexpressing HXT14 strains. The mechanism of resistance in the HXT13 overexpressing strain was due to increased ATP-independent MI efflux. However, resistance to MI of the HXT13-overexpressing strain did not extend to other drugs including the echinocandins, hotericin B, azoles, cycloheximide and sulfometuron methyl, ruling out the involvement of HXT13 in multidrug resistance. In summary, we have identified a new function of the hexose sugar transporter gene HXT13 when overexpressed in S. cerevisiae, namely, in efflux of MI and in mediating MI resistance.
Dual‐Functionalisation of Fluorophores for the Preparation of Targeted and Selective Probes
Publisher: Wiley
Date: 02-09-2020
Bis[zinc(ii)dipicolylamino]-functionalised peptides as high affinity receptors for pyrophosphate ions in water
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CC40937F
Abstract: A library of bis[zinc(II)dipicolylamine]-functionalised linear peptides was prepared using an efficient solid phase peptide synthesis approach and their use as chemosensors for anions in water was investigated using indicator displacement assays. High affinity and selectivity for pyrophosphate (PPi) over adenosine triphosphate (ATP) and adenosine diphosphate (ADP) were observed and additional aromatic side chains provided enhanced discrimination between PPi and ATP.
A study of the scope of the bismethoxycarbonylation of norbornene systems
Publisher: Elsevier BV
Date: 02-1995
Selective Removal of Sulfate from Water by Precipitation with a Rigid Bis‐amidinium Compound
Publisher: Wiley
Date: 14-02-2023
Abstract: A simple, readily prepared biphenyl bis‐amidinium compound ( 1⋅Cl 2 ) is able to selectively precipitate sulfate from water. The precipitant is effective at concentrations as low as 1 mM and shows complete selectivity against monovalent anions, and high selectivity even against CO 3 2− and HPO 4 2− . It is highly effective ( % sulfate removed) in both seawater and highly acidic conditions relevant to mining waste‐streams. X‐ray crystallography reveals that 1⋅SO 4 forms a tightly packed, anhydrous, structure where each sulfate anion receives eight hydrogen bonds from amidinium N−H hydrogen bond donors.
Cover Feature: Synthesis of Nitro‐Aryl Functionalised 4‐Amino‐1,8‐Naphthalimides and Their Evaluation as Fluorescent Hypoxia Sensors (Chem. Eur. J. 44/2020)
Publisher: Wiley
Date: 13-07-2020
Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes
Publisher: Elsevier BV
Date: 05-2007
DOI: 10.1016/J.BMC.2007.03.018
Abstract: A series of bis(pyridinium)alkanes have been prepared and their antifungal activity, haemolytic activity and ability to inhibit fungal phospholipase B1 have been investigated, together with those of the commercially available antiseptics octenidine and dequalinium. Removal of the amino substituents from the pyridinium rings resulted in a significant decrease in antifungal activity. However, shortening or removing the alkyl chains attached to the amino groups had little effect on antifungal activity and significantly reduced haemolytic activity. Only octenidine was a strong inhibitor of fungal phospholipase B1.
Control of structural isomerism in noncovalent hydrogen-bonded assemblies using peripheral chiral information
Publisher: American Chemical Society (ACS)
Date: 04-2000
DOI: 10.1021/JA9936262
The synthesis of novel thiazole containing cyclic peptides via cyclooligomerisation reactions
Publisher: Georg Thieme Verlag KG
Date: 11-1999
DOI: 10.1055/S-1999-2942
In vitro activity of miltefosine as a single agent and in combination with voriconazole or posaconazole against uncommon filamentous fungal pathogens
Publisher: Oxford University Press (OUP)
Date: 16-07-2013
DOI: 10.1093/JAC/DKT282
Abstract: Antifungal treatment of uncommon filamentous fungal infections is problematic. This study determined the in vitro susceptibility of miltefosine, as a single agent and in combination with posaconazole or voriconazole, against these pathogens. Susceptibility to miltefosine of 34 uncommon filamentous fungi was tested using CLSI broth microdilution M38-A2 methodology. Twenty isolates were studied for potential synergy using miltefosine osaconazole and miltefosine/voriconazole combinations and the chequerboard microdilution assay. MICs of miltefosine were high (in general, >8 mg/L) for most isolates compared with hotericin B, echinocandins and the azoles. Miltefosine had greatest activity against Scedosporium spp., Lichtheimia corymbifera and Rhizomucor sp. (MICs ≤ 4 mg/L). Miltefosine in combination either with posaconazole or voriconazole demonstrated synergy [fractional inhibitory concentration index (FICI) ≤ 0.5] in 12 instances (11 isolates): miltefosine osaconazole combinations were synergistic against 3 of 4 Fusarium oxysporum strains (FICI range 0.37-0.5) and 5 of 10 mucormycete strains (FICI range 0.06-0.5). The combination of voriconazole with miltefosine showed synergy against one Scedosporium prolificans isolate and three mucormycetes-a single strain each of L. corymbifera, Rhizopus oryzae and Rhizomucor sp. No antagonism was observed. Miltefosine demonstrated synergy in 8/20 (40%) and 4/20 (20%) instances when combined with posaconazole and voriconazole, respectively. Synergy was most often observed against F. oxysporum and the mucormycetes. Study of miltefosine/azole combinations as a novel antifungal approach is indicated.
Synthesis, antifungal, haemolytic and cytotoxic activities of a series of bis(alkylpyridinium)alkanes
Publisher: Elsevier BV
Date: 09-2009
DOI: 10.1016/J.BMC.2009.07.037
Abstract: A series of bis(alkylpyridinium)alkanes with a twelve carbon spacer between the positive charges was synthesised and their antifungal activity has been investigated. Compounds with 2-pentyl, 4-pentyl, 4-hexyl, 4-octyl, 4-propylbenzene, 3,4-dipentyl, 4-(5'-nonyl) and 3-methyl,4-pentyl head groups were the most potent antifungal agents with MICs in the range of 1.4-2.7 microM against reference strains of both Cryptococcus neoformans and Candida albicans.
Expanding the Breadth of 4‐Amino‐1,8‐naphthalimide Photophysical Properties through Substitution of the Naphthalimide Core
Publisher: Wiley
Date: 06-03-2018
Abstract: Fluorescent sensors that illuminate specific molecules and chemical events allow the selective and sensitive study of the cellular environment. At the centre of this technology lies the fluorescent reporter molecule, and it is therefore crucial to provide a breadth of fluorophores with varying photophysical and biological behaviour. 4-Amino-1,8-naphthalimides are commonly employed in fluorescent sensors, but the narrow range of structural derivatives limits versatility of application. Here we report the synthesis and investigation of a set of twelve 4-amino-1,8-naphthalimides bearing an additional substituent on the aromatic core. Photophysical characterisation and time-dependent density functional theory studies provided insights into the structure-photophysical property relationships of these derivatives, which show an expanded range of emission wavelengths and other photophysical properties. These compounds could all be visualised within cells by confocal microscopy, showing cytoplasmic or lipid droplet localisation. Our studies have demonstrated that simple structural modification of 4-amino-1,8-naphthalimides provides derivatives with considerable breadth of behaviour that lend valuable versatility to the design of fluorescent sensors.
Synthesis of backbone modified cyclic peptides bearing dipicolylamino sidearms
Publisher: Elsevier BV
Date: 02-2011
Selective recognition of pyrophosphate in water using a backbone modified cyclic peptide receptor
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B606917G
Abstract: A cyclic peptide based receptor, bearing two dipicolylamino arms complexed to zinc(II) ions, binds pyrophosphate ions with high affinity and selectivity in aqueous solution as determined using an indicator displacement assay.
Pushing the limits of copper mediated azide-alkyne cycloaddition (CuAAC) to conjugate polymeric chains to cyclic peptides
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2PY00510G
Synthetic transporters for sulfate: a new method for the direct detection of lipid bilayer sulfate transport
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3SC52006D
Synthesis of Side-Chain Modified Peptides Using Iterative Solid Phase 'Click' Methodology
Publisher: CSIRO Publishing
Date: 2017
DOI: 10.1071/CH16567
Abstract: A series of side-chain modified peptides have been prepared via an iterative sequence of peptide couplings and azide–alkyne cycloadditions (‘click’ reactions) using Fmoc-solid phase peptide synthesis. This efficient modular synthetic route allows the systematic and sequential incorporation of a variety of side-chain modifications onto short peptides. The versatility of this approach was demonstrated by the synthesis of a series of short peptides with appended anion recognition motifs and fluorescent indicators.
Selective Solvent Extraction of Silver(I) by Tris-Pyridyl Tripodal Ligands and X-Ray Structure of a Silver(I) Coordination Polymer Incorporating One Such Ligand
Publisher: CSIRO Publishing
Date: 2015
DOI: 10.1071/CH14540
Abstract: Two tripodal ligands, each derived from 1,1,1-tris(hydroxymethyl)ethane and terminated respectively by 4-pyridyl (L1) and 2-pyridyl groups (L2), have been synthesised. Competitive seven-metal extraction studies (H2O/CHCl3) incorporating equal concentrations of cobalt(ii), nickel(ii), copper(ii), zinc(ii), silver(i), cadmium(ii), and lead(ii) in the aqueous phase and L1 or L2 in the organic phase showed selective extraction of silver(i) in each case. A parallel solvent extraction experiment involving a related tripodal tris-pyridyl ligand (L3) based on a 1,3,5-substituted aryl ring scaffold and incorporating thioether sulfurs in each tripod arm also showed extraction selectivity for silver(i) extraction efficiencies towards this metal ion fall in the order L3 L1 L2. Physical data are in accord with L1 forming a capsule-like complex of type [Ag3L12]3+ in which silver ions link pairs of pyridyl groups from different ligands. In contrast, L2 yields a complex of type [Ag2L2(NO)3]n whose X-ray structure showed it to be a two-dimensional coordination polymer in which the three pyridyl donors of each L2 coordinate to three silver(i) centres, two of which are crystallographically distinct, with the centres also bonded to bidentate and/or bridging bidentate nitrato groups.
Triazole–containing zinc(II)dipicolylamine-functionalised peptides as highly selective pyrophosphate sensors in physiological media
Publisher: Informa UK Limited
Date: 29-01-2016
Interaction of Copper(II) with Ditopic Pyridyl-β-diketone Ligands: Dimeric, Framework, and Metallogel Structures
Publisher: American Chemical Society (ACS)
Date: 10-03-2011
DOI: 10.1021/CG101629W
Mono- and dinucleating Ni(II), Cu(II), Zn(II) and Fe(III) complexes of symmetric and unsymmetric Schiff bases incorporating salicylimine functions – Synthetic and structural studies
Publisher: Elsevier BV
Date: 05-2014
Investigating the scope of pseudoproline assisted peptide cyclization
Publisher: Elsevier BV
Date: 10-2014
An Area‐Specific, International Community‐Led Approach to Understanding and Addressing Equality, Diversity, and Inclusion Issues within Supramolecular Chemistry
Publisher: Wiley
Date: 08-03-2021
Abstract: Diversity, equality, and inclusion (DEI/EDI) are pressing issues in chemistry and the natural sciences. In this Essay we share how an area‐specific approach is “calling in” the community so that it can act to address EDI issues, and support those who are marginalised. Women In Supramolecular Chemistry (WISC) is an international network that aims to support equality, ersity, and inclusion within supramolecular chemistry. WISC has taken a field‐specific approach using qualitative research methods with scientists to identify the support that is needed and the problems the supramolecular community needs to address. Herein, we present survey data from the community which highlight the barriers that are faced by those who take career breaks for any reason, a common ex le is maternity leave, and the importance of mentoring to aid progression post‐PhD. In conclusion, we set out an interdisciplinary and creative approach to addressing EDI issues within supramolecular chemistry.
Janus cyclic peptide-polymer nanotubes
Publisher: Springer Science and Business Media LLC
Date: 13-11-2013
DOI: 10.1038/NCOMMS3780
Abstract: Self-assembled nanotubular structures have numerous potential applications but these are limited by a lack of control over size and functionality. Controlling these features at the molecular level may allow realization of the potential of such structures. Here we report a new generation of self-assembled cyclic peptide-polymer nanotubes with dual functionality in the form of either a Janus or mixed polymeric corona. A 'relay' synthetic strategy is used to prepare nanotubes with a demixing or mixing polymeric corona. Nanotube structure is assessed in solution using (1)H-(1)H nuclear Overhauser effect spectroscopy NMR, and in bulk using differential scanning calorimetry. The Janus nanotubes form artificial pores in model phospholipid bilayers. These molecules provide a viable pathway for the development of intriguing nanotubular structures with dual functionality via a demixing or a mixing polymeric corona and may provide new avenues for the creation of synthetic transmembrane protein channel mimics.
Fluorescent sensing arrays for cations and anions
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7AN01200D
Abstract: A review of fluorescent sensing arrays for anions and cations, highlighting promising strategies and directions for future research.
Editorial
Publisher: Informa UK Limited
Date: 05-02-2018
Synchrotron X-ray fluorescence studies of a bromine-labelled cyclic RGD peptide interacting with individual tumor cells
Publisher: International Union of Crystallography (IUCr)
Date: 07-02-2013
An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (±)-pancracine
Publisher: Royal Society of Chemistry (RSC)
Date: 2001
DOI: 10.1039/B102252K
Total synthesis and assignment of the side chain stereochemistry of LI-F04a: An antimicrobial cyclic depsipeptide
Publisher: American Chemical Society (ACS)
Date: 07-07-2010
DOI: 10.1021/OL101254M
Abstract: The total synthesis of the potent antifungal and antibiotic cyclic depsipeptide LI-F04a and its side chain epimer was accomplished using macrolactonization to assemble the cyclic peptide core, followed by attachment of the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain. The side chain was assembled by Yamaguchi-Hirao alkylation of both enantiomers of a chiral epoxide to provide a pair of enantiomeric side chains. The attachment of both these chains to the cyclic peptide allowed the absolute configuration of the side chain hydroxyl group in LI-F04a to be assigned as (R).
A macrocyclic fluorescent probe for the detection of citrate
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3OB01442H
Pseudoprolines as removable turn inducers: Tools for the cyclization of small peptides
Publisher: American Chemical Society (ACS)
Date: 12-11-2004
DOI: 10.1021/JO0484732
Abstract: The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.
Tunable Length of Cyclic Peptide-Polymer Conjugate Self-Assemblies in Water
Publisher: American Chemical Society (ACS)
Date: 19-09-2016
DOI: 10.1021/ACSMACROLETT.6B00586
Abstract: Polymers conjugated to cyclic peptides capable of forming strong hydrogen bonds can self-assemble into supramolecular bottlebrushes even in aqueous solutions. However, controlling the aggregation of these supramolecular assemblies remains an obstacle that is yet to be overcome. By introducing pH-responsive poly(dimethylamino ethyl methacrylate) (pDMAEMA) arms, the repulsive forces were tuned by adjusting the degree of protonation on the polymer arms. Neutron scattering experiments demonstrated that conjugates in an uncharged state will self-assemble into supramolecular bottlebrushes. Reducing the pH in the system led to a decrease in the number of aggregation, which was reversible by addition of base. Potentiometric titration showed a correlation between the number of aggregation and the degree of ionization of the pDMAEMA arms. Hence, a balance between the strength of the hydrogen bonds and the repulsive electrostatic interactions determines the number of aggregation and extent of self-assembly. The presented work demonstrates that conjugate self-association can be controlled by tuning the charge density on the conjugated polymer arms, paving the way for the use of responsive cyclic peptide conjugates in pharmaceutical applications.
Colorimetric and luminescent sensors for chloride: Hydrogen bonding vs deprotonation
Publisher: American Chemical Society (ACS)
Date: 29-10-2013
DOI: 10.1021/OL402500Q
Abstract: The synthesis and photophysical properties of four squaramide based fluorescent anion sensors (1-4) are described. These luminescent compounds showed selectivity for Cl(-) over various other anions with concomitant changes in both their UV/visible and fluorescence properties upon Cl(-) addition, attributed to initial H-bonding followed by NH deprotonation in the presence of excess Cl(-), signaled by a color change. The nature of the electron withdrawing aryl substituents is directly related to the H-bonding ability/acidity of the squaramide protons and can be used to tune the deprotonation behavior.
Modular design for the controlled production of polymeric nanotubes from polymer/peptide conjugates
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1PY00202C
Synthesis of cyclogossine B using a traceless pseudoproline turn-inducer
Publisher: CSIRO Publishing
Date: 2010
DOI: 10.1071/CH09643
Abstract: The first synthesis of the cyclic octapeptide, cyclogossine B, has been achieved, confirming the reported structure of this natural product. Cyclization of a linear precursor containing a cysteine-derived thiazolidine as a traceless turn-inducer occurred in significantly higher yields than cyclization of the analogous alanine-containing precursor under identical conditions. Deprotection of the thiazolidine followed by desulfurization provided cyclogossine B in good overall yield, indicating that cysteine-derived pseudoprolines can be effectively used as traceless turn-inducers to facilitate the cyclization of small peptides.
Neutral cryptand-like cyclic peptide–thiourea receptors for selective recognition of sulphate anions in aqueous solvents
Publisher: Informa UK Limited
Date: 18-11-2011
Synthetic, structural, electrochemical and solvent extraction studies of neutral trinuclear Co(ii), Ni(ii), Cu(ii) and Zn(ii) metallocycles and tetrahedral tetranuclear Fe(iii) species incorporating 1
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B716653B
Abstract: Uncharged complexes, formulated as trimeric metallocycles of type [M3(L(1))3(Py)6] (where M = cobalt(II), nickel(II) and zinc(II) and L(1) is the doubly deprotonated form of a 1,4-phenylene linked bis-beta-diketone ligand of type 1,4-bis(RC(O)CH2C(O))C6H4 (R = t-Bu)) have been synthesised, adding to related, previously reported complexes of these metals with L(1) (R = Ph) and copper(ii) with L(1) (R = Me, Et, Pr, t-Bu, Ph). New lipophilic ligand derivatives with R = hexyl, octyl or nonyl were also prepared for use in solvent extraction experiments. The X-ray structures of H2L(1) (R = t-Bu) and of its trinuclear (triangular) nickel(II) complex [Ni3(L(1))3(Py)6].3.5Py (R = t-Bu) are also presented. Electrochemical studies of H2L(1), [Co3(L(1))3(Py)6], [Ni3(L(1))3(Py)6], [Cu3(L(1))3], [Zn3(L(1))3(Py)6] and [Fe4(L(1))6] (all with R = t-Bu) show that oxidative processes for the complexes are predominantly irreversible, but several ex les of quasireversible behaviour also occur and support the assignment of an anodic process, seen between +1.0 and +1.6 V, as involving metal-centred oxidations. The reduction behaviour for the respective metal complexes is not simple, being irreversible in most cases. Solvent extraction studies (water/chloroform) involving the systematic variation of the metal, bis-beta-diketone and heterocyclic base concentrations have been performed for cobalt(II) and zinc(II) using a radiotracer technique in order to probe the stoichiometries of the respective extracted species. Significant extraction synergism was observed when 4-ethylpyridine was also present with the bis-beta-diketone ligand in the chloroform phase. Competitive extraction studies demonstrated a clear uptake preference for copper(II) over cobalt(II), nickel(II), zinc(II) and cadmium(II).
PH-Responsive, Amphiphilic Core-Shell Supramolecular Polymer Brushes from Cyclic Peptide-Polymer Conjugates
Publisher: American Chemical Society (ACS)
Date: 20-11-2017
Unusual Absence of Head-to-Tail Chains in the Crystal Structure of Glycyl-l-glutamyl-l-phosphoseryl-l-leucine
Publisher: Springer Science and Business Media LLC
Date: 22-06-2012
High affinity sulfate binding in aqueous media by cyclic peptides with thiourea arms
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C2CC37686E
Abstract: Tripodal thioureas based on a cyclic peptide scaffold have been synthesised and their anion binding properties evaluated. These receptors show high affinity towards sulfate ions in aqueous solution.
Synthesis of full length and truncated microcin B17 analogues as DNA gyrase poisons
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3OB42516A
Abstract: Using a combination of solid-phase peptide synthesis and fragment assembly strategies a library of full-length and truncated analogues of the antibacterial post-translationally modified peptide microcin B17 have been synthesised. Both antibacterial and DNA gyrase poisoning activities are also described for the synthetic analogues.
Erratum: Effective Am(iii)/Eu(iii) separations using 2,6-bis(1,2,4-triazin-3-yl)pyridine (BTP) functionalised titania particles and hierarchically porous beads(Chemical Communications (2015) DOI 10.1039/c5cc03957f.)
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CC90295A
Abstract: Correction for ‘Effective Am( iii )/Eu( iii ) separations using 2,6-bis(1,2,4-triazin-3-yl)pyridine (BTP) functionalised titania particles and hierarchically porous beads’ by J. Veliscek-Carolan et al. , Chem. Commun. , 2015, DOI: 10.1039/c5cc03957f.
Reversible Pressure-Controlled Depolymerization of a Copper(II)-Containing Coordination Polymer
Publisher: Wiley
Date: 16-08-2017
Abstract: A unique pressure-induced Cu-N bond breaking/bond forming reaction is reported. The variation of pressure on a single crystal of a one-dimensional copper- (II)-containing coordination polymer (Cu
Water-soluble and pH-responsive polymeric nanotubes from cyclic peptide templates
Publisher: Wiley
Date: 07-01-2013
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