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-gl...

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Bibliographic Details
Published in:Carbohydrate research 2002-11, Vol.337 (21-23), p.1929-1934
Main Authors: Li, Qin, Li, Hui, Li, Qing, Lou, Qing-Hua, Su, Bin, Cai, Meng-Shen, Li, Zhong-Jun
Format: Article
Language:English
Subjects:
Antigens, Neoplasm - chemistry
Carbohydrate Conformation
Carcinoma, Hepatocellular - immunology
Haptens - chemistry
Humans
Magnetic Resonance Spectroscopy
Oligosaccharides - chemical synthesis
Oligosaccharides - immunology
Sulfates
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Summary: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.
ISSN:0008-6215
DOI:10.1016/S0008-6215(02)00291-4