ArticleAngewandte Chemie (International ed. in English)2023
Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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Who cites it
6 citing papers in PubMed, 11 citations in OpenAlex.
- Catalyst-Free Biotin Conjugation Onto Poly(Styrene-co-Butadiene) Mediated by an Orthogonal Agent Comprising Nitrile N-Oxide and Blocked Isocyanate.Macromolecular rapid communications · 2026Article
- Sydnthiones are versatile bioorthogonal hydrogen sulfide donors.Nature communications · 2024Article
- Reactivity Profiling for High-Yielding Ynamine-Tagged Oligonucleotide Click Chemistry Bioconjugations.Bioconjugate chemistry · 2024Article
- Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling.Beilstein journal of organic chemistry · 2024Article
- Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.Angewandte Chemie (International ed. in English) · 2023Article
- Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
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.
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Registered trials
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