Synthesis of 4-deoxy-4-thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan

Academic Article

Abstract

  • The first chemical synthesis of disaccharides, octyl 5-O-(4-deoxy-4-thio- α-D-arabinofuranosyl)-α-D-arabinofuranoside 1 and octyl 5-O-(4-deoxy-4-thio-β-D-arabinofuranosyl)-α-D-arabinofuranoside 2 incorporating 4-deoxy-4-thioarabinose is described. Designed to mimic components of mycobacterial arabinogalactan, a major and essential constituent of the cell wall of tuberculosis and related bacteria, the compounds may disrupt cell wall biogenesis. A variety of coupling methods have been investigated before finding satisfactory techniques useful for thiofuranoses. Reductive deprotection of the sulfur-containing species is problematic, though lithium naphthalenide has proved to be an effective technique.
  • Author List

  • Khare NK; Reynolds RC; Maddry JA
  • Start Page

  • 1748
  • End Page

  • 1752
  • Volume

  • 47
  • Issue

  • 11