Stereoselective synthesis of N-galactofuranosyl amides

Carbohydr Res. 2011 Mar 1;346(4):465-71. doi: 10.1016/j.carres.2010.12.020. Epub 2010 Dec 31.

Abstract

α- or β-Galactofuranosyl (Galf) amides can be synthesized with high stereoselectivity by traceless Staudinger ligation starting from unprotected β-galactofuranosyl azide or tetra-O-acetyl-β-galactofuranosyl azide, respectively. The resulting Galf amides are hitherto unknown molecules, with interesting potential as inhibitors of mycobacterial growth.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology
  • Azides / chemistry
  • Furans / chemistry*
  • Galactose / chemistry*
  • Glycosides / chemistry*
  • Mycobacterium tuberculosis / drug effects
  • Stereoisomerism

Substances

  • Amides
  • Antitubercular Agents
  • Azides
  • Furans
  • Glycosides
  • Galactose