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

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. (C) 1996 Elsevier Science Ltd