10.1016/j.tet.2018.04.082
The study presents a simplified method for beta-glycosylation of peptides, focusing on the activation of S-phenyl thioglycosides using N-iodosuccinimide and catalytic copper(I) triflate. This method effectively promotes beta-O-glycosylation at serine and threonine hydroxyls in "mono-," di-, and tripeptides, as well as beta-N-glycosylation of asparagine-containing peptides. A key advantage is the minimization of undesired amide O-glycosylation. The study also develops streamlined deprotection sequences based on global hydrogenolysis, leading to the parent glycopeptides. The core glycopeptide region for biological protein N-glycosylation has been synthesized, purified, and characterized. The research provides an efficient process for O- and N-glycosylation of peptides, which is beneficial for multistep preparations, especially those limited by material availability.