title: A mild TCEP-based para-azidobenzyl cleavage strategy to transform reversible cysteine thiol labelling reagents into irreversible conjugates.
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.
authors.affiliation: Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK. v.chudasama@ucl.ac.uk.
authors.forename: Antoine
authors.initials: A
authors.lastname: Maruani
authors.forename: Shamim
authors.initials: S
authors.lastname: Alom
authors.forename: Pierre
authors.initials: P
authors.lastname: Canavelli
authors.forename: Maximillian T W
authors.initials: MT
authors.lastname: Lee
authors.forename: Rachel E
authors.initials: RE
authors.lastname: Morgan
authors.forename: Vijay
authors.initials: V
authors.lastname: Chudasama
authors.forename: Stephen
authors.initials: S
authors.lastname: Caddick
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013194:Staining and Labeling; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D001565:Benzoates; D003545:Cysteine; D007202:Indicators and Reagents; D010720:Phosphines; D013438:Sulfhydryl Compounds; C080938:tris(2-carboxyethyl)phosphine