Total synthesis of the carbohydrate-protein linkage region common to several mammalian proteoglycans.
A stereocontrolled synthesis of beta-D-GlcpA-(1--> 3)-beta-D-Galp-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Xylp-(1 --> O)-L-Ser-Gly, the common glycopeptide sequence of the carbohydrate-protein linkage region of most mammalian proteoglycans, was achieved by use of O-[2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-beta-D-glucopyranosyluronate] -(1-->3)-O-(2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl)-(1-->3)-O-(2,4, 6-tri -O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-2,3-di-O-benzoyl-alpha, beta-D- xylopyranosyl trichloroacetimidate as the key intermediate. Condensation of this glycosyl donor with suitably protected L-seryl-glycine dipeptide segments, and peptide chain elongation, allowed the construction in high yield of complex structures of this linkage region.
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
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008322:Mammals / Q000378:metabolism*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011509:Proteoglycans / Q000138:chemical synthesis* / Q000737:chemistry
D004151:Dipeptides; D009844:Oligosaccharides; D011509:Proteoglycans