A mild TCEP-based para-azidobenzyl cleavage strategy to transform reversible cysteine thiol labelling reagents into irreversible conjugates†
Antoine Maruani,Shamim Alom,Pierre Canavelli,Maximillian T. W. Lee,Rachel E. Morgan,Vijay Chudasama,Stephen Caddick
Chemical Communications Pub Date : 11/12/2014 00:00:00 , DOI:10.1039/C4CC08515A
Abstract

It has recently emerged that the succinimide linkage of a maleimide thiol addition product is fragile, which is a major issue in fields where thiol functionalisation needs to be robust. Herein we deliver a strategy that generates selective cysteine thiol labelling reagents, which are stable to hydrolysis and thiol exchange.

Graphical abstract: A mild TCEP-based para-azidobenzyl cleavage strategy to transform reversible cysteine thiol labelling reagents into irreversible conjugates