Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides

Abstract

Glycosyl radicals, produced under mild photoredox conditions, show unique utility in the preparation of C-linked glycoconjugates. We herein report the construction of C-glycosidic bonds on α,β-dehydroalanine (DHA) of peptides with easily available glycosyl bromides as glycosyl radical precursors under highly anomeric control, leading to C-glycosylation modifications of peptides. This method not only has outstanding functional group compatibility, but also is feasible in near-physiological conditions (pH ∼ 7 and temperature T ≤ 37 °C in aqueous media).