Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans

Article abstract of DOI:10.1016/0008-6215(91)89043-F

2,3,4,6-Tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate was condensed with benzyl 2,3-O-isopropylidene-β-D-xylopyranoside to give the corresponding β-(1->4)-linked disaccharide derivative, which was transformed into 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-xylopyranosyl trichloroacetimidate.This glycosyl donor was condensed with a set of selectively C,N-protected L-seryl-glycine dipeptide units.Selective deblocking at the C- or N-termini of the glycosylated or non-glycosylated dipeptide segments, and coupling using the mixed-anhydride procedure allowed the construction in high yield of partially or fully glycosylated oligopeptides from the carbohydrate-protein linkage region of proteoglycans.