Leveraging the Mukaiyama oxidation–reduction condensation reaction for on-resin aryl thio-esterification for bio-conjugation

Abstract

A room-temperature Mukaiyama oxidation–reduction condensation inspired thioesterification methodology has been developed to afford aryl C^α-terminal peptide thioesters on-resin. The conditions herein feature mild reactions compatible with all Fmoc-SPPS protocols offering direct access to this critical arylthioester scaffold. This one-pot synthesis to aryl-thioester functionalised peptides facilitates peptide/protein synthesis by native chemical ligation.