Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.
Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-alpha-D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-beta-D-glucopyranosyl)uronate-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-beta-D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N',N"-tri-(5-[4-O-methyl-beta-D-glucopyranosyluronic acid-(1-->6)-beta-D-galactopyranosyloxy]pentylcarbonylaminoethyl)-1,3,5-benzenetriamide and N,N',N"-tri-(5-[4-O-methyl-beta-D-glucopyranosyluronic acid (1-->6)-beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranosyloxy]pentylcarbonylaminoethyl)-1,3,5-benzenetriamide.
Hada
N
N
Kyoritsu College of Pharmacy, Shibakoen 1-5-30, Minato-ku, 105-8512, Tokyo, Japan.
Ogino
T
T
Yamada
H
H
Takeda
T
T
D002240:Carbohydrate Sequence; D000939:Epitopes / Q000737:chemistry*; D019684:Magnoliopsida; D008956:Models, Chemical; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis; D010368:Pectins / Q000737:chemistry* / Q000276:immunology
D000939:Epitopes; D009005:Monosaccharides; D009844:Oligosaccharides; D010368:Pectins