TCEP-Enabled Click Modification of Glycidyl-Bearing Polymers with Biorelevant Sulfhydryl Molecules: Toward Chemoselective Bioconjugation Strategies.

ABSTRACT: Thiol-epoxy ring opening is a highly efficient and versatile click reaction for postpolymerization modification, ideal for the conjugation of sulfhydryl-containing biomolecules. This study investigated the reactivity of thiols, disulfides, and amines toward glycidyl-bearing polymers, aiming to optimize thiol conjugation using tris(2-carboxyethyl)phosphine (TCEP) as a disulfide-reducing agent. Epoxide groups were introduced via glycidyl methacrylate (GMA) polymerized by ATRP to yield PGMA homopolymers and poly(ε-caprolactone) (PCL)-based block copolymers. ¹H NMR confirmed quantitative thiol functionalization, while amines showed poor reactivity. l-cysteine conjugation further demonstrated the reaction's chemoselectivity. Thioglycerol conjugation yielded poly(2-hydroxy-3-(thioglyc

SUBMITTER: Porello I 

PROVIDER: S-EPMC12344704 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature