Synthesis of glycopeptide sequences of repeating units of the mucins MUC 2 and MUC 3 containing oligosaccharide side-chains with core 1, core 2, core 3, core 4 and core 6 structure

Abstract

An efficient synthesis of glycosylamino acid building blocks containing core 1, core 2, core 3, core 4 or core 6 mucin core oligosaccharide structures linked O-glycosidically to threonine has been developed. These building blocks 6, 10, 16, 24 and 30 can be used directly for coupling reactions in a glycopeptide synthesis. In a multiple-column solid-phase synthesis, they have been used to prepare different series of glycopeptides. Decapeptide sequences have been synthesized from repeating units of the mucins MUC 2 and MUC 3 in which different threonine residues are each systematically glycosylated with an oligosaccharide of core 1, core 2, core 3, core 4 or core 6 structure. Glycopeptides are substrates for the study of the biosynthesis of the saccharide side-chains of mucins.