Chemical synthesis of cyclic galactooligofuranosides isolated from enzymatic degradation products of cell wall arabinogalactan of Mycobacterium tuberculosis

Org Lett. 2008 Jun 19;10(12):2373-6. doi: 10.1021/ol800530u. Epub 2008 May 22.

Abstract

Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1-->5)-beta- and (1-->6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular, cyclooligomerization of the (1-->6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Wall / chemistry*
  • Cell Wall / metabolism
  • Cyclization
  • Galactans / chemical synthesis*
  • Galactans / chemistry
  • Glycosylation
  • Molecular Structure
  • Mycobacterium tuberculosis / chemistry*
  • Mycobacterium tuberculosis / metabolism
  • Polysaccharides, Bacterial / chemistry*
  • Stereoisomerism

Substances

  • Galactans
  • Polysaccharides, Bacterial
  • arabinogalactan