Preparation of a glycopeptide analogue of type II collagen — Use of acid labile protective groups for carbohydrate moieties in solid phase synthesis of O-linked glycopeptides

Abstract

A glycopeptide analogue of the immunodominant T cell epitope on type II collagen has been prepared by solid phase synthesis. Preparation of a glycosylated amino acid from two monosaccharide units that carried silyl and isopropylidene protective groups and Fmoc 5-hydroxynorvaline was essential for the synthesis. After assembly of the glycopeptide the carbohydrate protective groups were removed simultaneously with acid catalyzed cleavage from the solid phase.