AI Article Synopsis
- Traditional bio-orthogonal reaction methods focus on creating fast-reacting reagent pairs that avoid metabolic breakdown, with glutathione (GSH) playing a key role in deactivating many reagents.
- This study reveals that GSH can actually enhance a specific Cu-catalysed (3+2) cycloaddition reaction between ynamines and azides by modulating the copper's oxidation state.
- The researchers utilized this GSH-mediated reactivity for dual sequential bio-orthogonal labeling of peptides and oligonucleotides, exploiting a tunable reaction rate based on the Cu:GSH ratio.
Article 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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10952886 | PMC |
| http://dx.doi.org/10.1002/anie.202313063 | DOI Listing |
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