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ChemInform Abstract: A Highly Convergent Total Synthetic Route to Glycopeptides Carrying a High-Mannose Core Pentasaccharide Domain N-Linked to a Natural Peptide Motif.

✍ Scribed by S. J. DANISHEFSKY; S. HU; P. F. CIRILLO; M. ECKHARDT; P. H. SEEBERGER

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199804204

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✦ Synopsis

A Highly Convergent Total Synthetic Route to Glycopeptides Carrying a High-Mannose Core Pentasaccharide Domain N-Linked to a Natural Peptide Motif.

-A novel and efficient synthesis of the pentasaccharide portion of asparagine-linked glycoproteins is established. Coupling of disaccharide acceptor glycal with glycal-derived trisaccharide thioethyl donor as key step provides the β-glucoside which is subsequently converted into the β-mannoside. Either during reduction of terminal azide or during coupling of resultant amino sugar with peptides the stereochemical integrity of the anomeric center in the carbohydrate domain can not be maintained and a mixture of anomeric glycopeptides is obtained. -(DANISHEFSKY, S.

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