ORCID Profile
0000-0003-0155-8877
Current Organisation
University of South Australia
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Publisher: American Chemical Society (ACS)
Date: 13-07-2021
DOI: 10.1021/ACS.BIOCONJCHEM.1C00287
Abstract: The applications of bioconjugation chemistry are rapidly expanding, and the addition of new strategies to the bioconjugation and ligation toolbox will further advance progress in this field. Herein, we present a detailed study of the Diels-Alder cycloaddition (DAC) reaction between pentafulvenes and maleimides in aqueous solutions and investigate the reaction as an emerging bioconjugation strategy. The DAC reactions were found to proceed efficiently, quantitatively yielding cycloadducts with reaction rates ranging up to ∼0.7 M
Publisher: American Chemical Society (ACS)
Date: 31-08-2021
Publisher: Beilstein Institut
Date: 06-09-2019
DOI: 10.3762/BJOC.15.209
Abstract: The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes. Tables providing comprehensive directories of fulvene cycloaddition chemistry are provided, including fulvene intramolecular and intermolecular cycloadditions complete with reactant partners and their resulting cyclic adducts, which provide a useful reference source for synthetic chemists working with fulvenes and complex polycyclic scaffolds.
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2TB00274D
Abstract: Highly efficient, selective and cytocompatible fulvene–maleimide cycloaddition chemistry was applied for the preparation of injectable, cell encapsulating/releasing hydrogels with tuneable gelation and degradation kinetics.
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2OB01453J
Abstract: Ligation chemistries are often required to perform under stringent conditions that preserve the integrity and function of (bio)conjugates, including specific biological buffers. To explore the versatility of the pentafulvene-maleimide ligation for (bio)conjugations, we studied the stability of the coupling partners and their Diels-Alder cycloaddition (DAC) in buffers used commonly in biological assays, protein chemistry and bioconjugates. The stability of 6,6-dialkylpentafulvene and maleimide derivatives to a panel of buffers with pH values between 3.7 and 10.1 was monitored via 1 H NMR spectroscopy. While the pentafulvene displayed excellent stability, hydrolysis of the maleimide was observed in several cases, although the extent of hydrolysis did not correlate with pH. For almost all buffers the pentafulvene-maleimide DAC proceeded efficiently and at a significantly faster rate than maleimide hydrolysis under the conditions studied. The buffer composition nor pH appeared to have a significant effect on the kinetics of the DAC with second-order rate constants ( k 2 ) ranging from 0.14 to 0.33 M -1 s -1 (23 ± 1 °C). This study highlights the versatility of the pentafulvene-maleimide ligation to proceed under a wide range of conditions relevant for (bio)conjugations and that maleimide hydrolysis in aqueous system may be promoted or inhibited by certain buffers.
Publisher: Elsevier BV
Date: 07-2020
No related grants have been discovered for Kirsten Platts.