Design and synthesis of unnatural heparosan and chondroitin building blocks

J Org Chem. 2011 May 6;76(9):3181-93. doi: 10.1021/jo200076z. Epub 2011 Apr 7.

Abstract

Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetylglucosamine / chemistry
  • Azides / chemistry
  • Chondroitin / chemistry*
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry*
  • Drug Design*
  • Heparitin Sulfate / chemistry*
  • Stereoisomerism
  • Sulfates / chemistry

Substances

  • Azides
  • Disaccharides
  • Sulfates
  • heparosan
  • Chondroitin
  • Heparitin Sulfate
  • Acetylglucosamine