Solid-phase synthesis of phosphoramidate-linked glycopeptide
D.M.M. Jaradat, H. Hamouda, C.P.R. Hackenberger – 2010
The 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.