Carbohydrate epitope structural elucidation by 1H-NMR spectroscopy of a new Mycobacterium kansasii phenolic glycolipid antigen

Eur J Biochem. 1990 Oct 24;193(2):449-57. doi: 10.1111/j.1432-1033.1990.tb19359.x.

Abstract

The complete primary structure of the carbohydrate moiety of a new phenolic glycolipid antigen namely PheGl K-IV from Mycobacterium kansasii was successfully established from only one- and two-dimensional 1H-NMR data. Among the scalar two-dimensional techniques, correlated spectroscopy with a 45 degree mixing pulse and phase-sensitive double-quantum-filtered correlated spectroscopy were selected, combined with two-dimensional dipolar techniques (nuclear Overhauser effect). These techniques using milligram of quantities native PheGl K-IV allowed the following monoacetylated tetrasaccharide to be proposed for its carbohydrate part: 4-O-Me-alpha-Manp-(1----3)-4-O-Ac-2-O-Me-alpha-Fucp-(1----3) -2-O-Me-alpha-Rhap- (1----3)-2,4-di-O-Me-alpha-Rhap. The PheGl K-IV shares, with the other phenolic glycolipids isolated from M. kansasii (K-I, K-II), a common core assigned to the lipid aglycone glycosylated by the monoacetylated trisaccharide part. It differs in the structure of the distal monosaccharide residue.

MeSH terms

  • Antigens, Bacterial / chemistry*
  • Antigens, Bacterial / immunology
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cell Wall / chemistry
  • Cell Wall / immunology
  • Epitopes / chemistry*
  • Epitopes / immunology
  • Glycolipids / chemistry*
  • Glycolipids / immunology
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Mycobacterium / immunology*

Substances

  • Antigens, Bacterial
  • Epitopes
  • Glycolipids