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: Qin Li, Hui Li, Qing Li, Qing-Hua Lou, Bin Su, Meng-Shen Cai, Zhong-Jun Li
• Journal: Carbohydrate research (Carbohydr Res) Vol. 337 Issue 21-23 Pg. 1929-34 (Nov 19 2002) ISSN: 0008-6215 [Print] Netherlands
• PMID: 12433458 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright 2002 Elsevier Science Ltd.

Chemical References

• 2-aminoethyl-3-O-sulfo-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-galactopyranosyl-(1-4)-3-O-sulfo-galactopyranosyl-(1-4)-beta-D-glucopyranoside
• Antigens, Neoplasm
• Haptens
• Oligosaccharides
• Sulfates

Topics

• Antigens, Neoplasm (chemistry)
• Carbohydrate Conformation
• Carcinoma, Hepatocellular (immunology)
• Haptens (chemistry)
• Humans
• Magnetic Resonance Spectroscopy
• Oligosaccharides (chemical synthesis, immunology)
• Sulfates