A novel mannose containing phenolic glycolipid from Mycobacterium kansasii

J Biol Chem. 1987 Nov 5;262(31):14879-84.

Abstract

Using high-performance liquid chromatography, a new kind of phenolic glycolipid quantitatively minor, called phenolic glycolipid-II, was isolated from a lipidic fraction of Mycobacterium kansasii. The structure was determined by fast atom bombardment-mass spectrometry and proton nuclear magnetic resonance spectroscopy, as: 2,4-di-O-Me-alpha-D-Manp(1----3) 4-O-Ac-2-O-Me-alpha-L-Fucp(1----3)2-O-Me- alpha-L-Rhap(1----3) 2,4-di-O-Me-alpha-L-Rhap 1----phenolphthiocerol dimycocerosate. Phenolic glycolipids I and II differ only by their distal monosaccharide hapten which is 2,6-dideoxy-4-O-Me-alpha-D-arabinohexopyranosyl and the 2,4-di-O-Me-alpha-D-mannopyranosyl, respectively. This sugar appears to be characteristic and apparently unique in the Mycobacterium genus. Moreover, phenolic glycolipids I and II constitute with the lipooligosaccharides two classes of antigens of M. kansasii.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Glycolipids / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Mannose / analysis*
  • Mass Spectrometry
  • Mycobacterium / analysis*
  • Phenols / analysis

Substances

  • Glycolipids
  • Phenols
  • Mannose