Solid‐Phase Synthesis of Phosphoramidate‐Linked Glycopeptides

Abstract

AbstractThe synthesis of stable glycopeptide mimetics is of particular interest in bioorganic chemistry to allow access of glycoconjugates for biological investigations. In this paper, a straightforward solid‐phase synthesis of a novel glycopeptide mimetic by a Staudinger phosphite reaction is presented. Thereby, a dimethyl phosphite containing peptide, which is obtained by standard phosphitylation of a Ser residue, is treated on the solid support with glycosyl azides, delivering phosphoramidate‐linked glycoconjugates. These artificial glycopeptides show excellent stability under acidic and physiological conditions.