title: Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma.
abstract: A disulfated tetrasaccharide fragment with a spacer arm of human hepatocellular carcinoma carbohydrate antigen SB(1a), namely, 2-aminoethyl 3-O-sulfo-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-sulfo-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside was synthesized via a [2 + 1 + 1] block building mode. In the last coupling step toward the trisaccharide acceptor 8, benzoyl protected galactosyl bromide donor 14 was found to be much more reactive than the acetyl-protected donors.
authors.affiliation: Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China.
authors.forename: Qin
authors.initials: Q
authors.lastname: Li
authors.forename: Hui
authors.initials: H
authors.lastname: Li
authors.forename: Qing
authors.initials: Q
authors.lastname: Li
authors.forename: Qing-Hua
authors.initials: QH
authors.lastname: Lou
authors.forename: Bin
authors.initials: B
authors.lastname: Su
authors.forename: Meng-Shen
authors.initials: MS
authors.lastname: Cai
authors.forename: Zhong-Jun
authors.initials: ZJ
authors.lastname: Li
mesh_terms: D000951:Antigens, Neoplasm / Q000737:chemistry*; D002236:Carbohydrate Conformation; D006528:Carcinoma, Hepatocellular / Q000276:immunology*; D006241:Haptens / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000276:immunology; D013431:Sulfates
chemical_list: C475340:2-aminoethyl-3-O-sulfo-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-galactopyranosyl-(1-4)-3-O-sulfo-galactopyranosyl-(1-4)-beta-D-glucopyranoside; D000951:Antigens, Neoplasm; D006241:Haptens; D009844:Oligosaccharides; D013431:Sulfates