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.

Titel
Solid-phase synthesis of phosphoramidate-linked glycopeptide
Verfasser
D.M.M. Jaradat, H. Hamouda, C.P.R. Hackenberger
Datum
2010
Kennung
10.1002/ejoc.201000627
Zitierweise
Eur. J. Org. Chem. 2010, 5004-5009
Art
Text
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