Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.
Angew Chem Int Ed Engl
; 62(50): e202313063, 2023 12 11.
Article
en En
| MEDLINE
| ID: mdl-37906440
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 CuGSH 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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1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Péptidos
/
Glutatión
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2023
Tipo del documento:
Article
País de afiliación:
Reino Unido