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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 solidphase 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 phosphoramidatelinked glycoconjugates. These artificial glycopeptides show excellent stability under acidic and physiological conditions.

The cover picture showsthe synthesis of a novel class of carbohydrate–peptide conjugates, which proceeds by a Staudingerphosphite reaction of glycosyl azides with phosphitylated peptides. The synthetic protocol is easy to perform, as the carbohydrate has to be added to the solidsupported peptide before the resulting glycoconjugate is cleaved from the resin by TFA treatment. The obtained phosphoramidatelinked glycopeptides derived from the dimethyl phosphitylated peptides are stable under acidic and physiological conditions. Details are discussed in the article by C. P. R. Hackenberger et al. on p. 5004 ff. The authors thank Nico Zapke and the “cowema.com medienlabor” for their contribution in designing the cover picture.