Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans.
2,3,4,6-Tetra-O-benzoyl-alpha-D-galactoyranosyl trichloroacetimidate was condensed with benzyl 2,3-O-isopropylidene-beta-D-xylopyranoside to give the corresponding beta-(1----4)-linked disaccharide derivative, which was transformed into 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl)- alpha-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 proteoglycan.
Rio
S
S
Laboratoire de Biochimie Structurale, U.R.A. 499, U.F.R. Faculté des Sciences, Université d'Orléans, France.
Beau
J M
JM
Jacquinet
J C
JC
D002240:Carbohydrate Sequence; D004187:Disaccharides; D006020:Glycopeptides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000737:chemistry; D011509:Proteoglycans / Q000737:chemistry*; D012694:Serine / Q000737:chemistry
D004187:Disaccharides; D006020:Glycopeptides; D009842:Oligopeptides; D011509:Proteoglycans; C073827:4-O-galactopyranosylxylose; D012694:Serine