Glutathione mediates control of dual differential bio-orthogonal labelling of biomolecules
Peschke, Frederik and Taladriz-Sender, Andrea and Andrews, Matthew J. and Watson, Allan J. B. and Burley, Glenn A. (2023) Glutathione mediates control of dual differential bio-orthogonal labelling of biomolecules. Angewandte Chemie International Edition, 62 (50). e202313063. ISSN 1521-3773 (https://doi.org/10.1002/anie.202313063)
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Abstract
Traditional approaches to bio-orthogonal reaction discovery have focused on developing reagent pairs that react with each other faster than they are metabolically degraded. Glutathione (GSH) is typically responsible for the deactivation of most bio-orthogonal reagents. Here we demonstrate that GSH promotes a Cu-catalysed (3+2) cycloaddition reaction between an ynamine and an azide. We show that GSH acts as a redox modulator to control the Cu oxidation state in these cycloadditions. Rate enhancement of this reaction is specific for ynamine substrates and is tuneable by the Cu:GSH ratio. This unique GSH-mediated reactivity gradient is then utilised in the dual sequential bio-orthogonal labelling of peptides and oligonucleotides via two distinct chemoselective (3+2) cycloadditions.
ORCID iDs
Peschke, Frederik, Taladriz-Sender, Andrea ORCID: https://orcid.org/0000-0002-8274-4761, Andrews, Matthew J., Watson, Allan J. B. and Burley, Glenn A.;-
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Item type: Article ID code: 87187 Dates: DateEvent11 December 2023Published13 November 2023Published Online31 October 2023Accepted5 September 2023SubmittedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > BionanotechnologyDepositing user: Pure Administrator Date deposited: 06 Nov 2023 15:38 Last modified: 23 Sep 2024 13:34 URI: https://strathprints.strath.ac.uk/id/eprint/87187