One-pot synthesis of a 3,6-branched hexaarabinogalactan using galactopyranosyl thioglycoside diol as a key glycosylating agent

J Asian Nat Prod Res. 2014;16(6):640-7. doi: 10.1080/10286020.2014.917084. Epub 2014 May 30.

Abstract

We present in this paper the efficient four-component one-pot synthesis of a fully protected hexaarabinogalactan 2 with di-branched structure by using D-thiogalactopyranoside 3,6-diol 3 as the central glycosylating agent. After global deprotection, 2 was converted into the 3-aminopropyl linker-containing free oligosaccharide 1 that is structurally related to ALR-5IIa-1-1, an arabino-3,6-galactan with intestinal immune system modulating activity.

Keywords: arabinogalactan; one-pot glycosylation; regioselective glycosylation; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Atractylodes / chemistry
  • Galactans / chemical synthesis*
  • Galactans / chemistry
  • Galactans / pharmacology
  • Glycosylation
  • Molecular Structure
  • Oligosaccharides / chemistry
  • Thioglycosides / chemistry

Substances

  • Galactans
  • Oligosaccharides
  • Thioglycosides
  • arabinogalactan