An efficient copper-catalyzed thioglycosylation of tryptophan and tryptophan-containing peptides with N-(thioglycosyl)succinimide has been developed. The methodology demonstrates broad substrate compatibility, encompassing diverse glycan donors (hexoses, pentoses, and disaccharides) and peptide backbones (di-, tri-, and tetrapeptides). Furthermore, the protocol was extended to S-arylation, S-alkylation, cysteinylation, thiocyanation, and selenoarylation, showcasing its versatility.
Wei et al. (Tue,) studied this question.