Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-beta-D-glucosamine at the reducing end

Carbohydr Res. 1998 Jun;309(2):161-74. doi: 10.1016/s0008-6215(98)00116-5.

Abstract

To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.

MeSH terms

  • Acetic Anhydrides
  • Acetylglucosamine / chemistry*
  • Carbohydrate Sequence
  • Glycosides / chemical synthesis*
  • Hyaluronic Acid / chemistry*
  • Indicators and Reagents
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oxidation-Reduction
  • Pyridinium Compounds

Substances

  • Acetic Anhydrides
  • Glycosides
  • Indicators and Reagents
  • Oligosaccharides
  • Pyridinium Compounds
  • pyridinium dichromate
  • acetic anhydride
  • Hyaluronic Acid
  • Acetylglucosamine