Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma

Carbohydr Res. 2002 Nov 19;337(21-23):1929-34. doi: 10.1016/s0008-6215(02)00291-4.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

  • 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