Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma.
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.
Li
Qin
Q
Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China.
Li
Hui
H
Li
Qing
Q
Lou
Qing-Hua
QH
Su
Bin
B
Cai
Meng-Shen
MS
Li
Zhong-Jun
ZJ
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
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