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.
Highlights
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
We deliver a strategy that generates selective cysteine thiol labelling reagents, which are stable to hydrolysis and thiol exchange
It has recently come to light that such an appendage is sub-optimal owing to issues of hydrolysis, and thiol exchange with reactive thiols in the blood.[14]
Summary
A mild TCEP-based para-azidobenzyl cleavage strategy to transform reversible cysteine thiol labelling reagents into irreversible conjugates† We deliver a strategy that generates selective cysteine thiol labelling reagents, which are stable to hydrolysis and thiol exchange.
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