Chemical Synthesis of α-d-Mannosylphosphate Serine Derivatives: A New Class of Synthetic Glycopeptides

Galal A. Elsayed; Geert-Jan Boons

doi:10.1055/s-2003-40344

LETTER

Chemical Synthesis of α-d-Mannosylphosphate Serine Derivatives: A New Class of Synthetic Glycopeptides

Galal A. Elsayed, Geert-Jan Boons*
Complex Carbohydrate Research Center, The University of Georgia, 220 Riverbend Road, Athens, GA 30602, USA
e-Mail: gjboons@ccrc.uga.edu;

Abstract

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Abstract

α-d-Mannosylphosphate serine derivatives were conveniently synthesized by reaction of benzyl or cyanoethyl phosphochloroamidites with 2,3,4,6-tetra-O-acetyl-d-mannose to give intermediate α-mannosyl phosphoramidites, which were successfully reacted with properly protected serine derivatives in the presence of 1H-tetrazole to give phosphite triesters which could be oxidized to phosphotriesters using t-BuOOH.

Key words

carbohydrates - glycopeptides - glycosyl phosphates - phosphoglycosylation - phosphochloroamidites

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