The structure of the O-specific polysaccharide of Citrobacter O16 containing glycerol phosphate

Eur J Biochem. 1994 Jan 15;219(1-2):653-61. doi: 10.1111/j.1432-1033.1994.tb19981.x.

Abstract

The O-specific polysaccharide, obtained by mild acid degradation of Citrobacter O16 lipopolysaccharide, consists of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-galactose, glycerol and phosphate in the ratios 2:2:2:1:1. Selective cleavage of the polysaccharide was carried out by Smith degradation, N-deacetylation-deamination and dephosphorylation with 48% hydrofluoric acid, which was accompanied by unexpected splitting of one of the glycosidic linkages. The structures of the oligosaccharides thus obtained were established using 1H- and 13C-NMR spectroscopy, including one-dimensional NOE, two-dimensional rotating-frame NOE, homonuclear and heteronuclear 13C, 1H correlation spectroscopy, and, for the Smith degradation product, positive- and negative-ion-mode fast-atom-bombardment MS and MS/MS with collision-induced dissociation. On the basis of these data and the results of methylation analysis, it was concluded that the O-specific polysaccharide has the following repeating unit structure: [formula: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Carbon Isotopes
  • Citrobacter / chemistry*
  • Citrobacter / growth & development
  • Glycerophosphates / analysis*
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Molecular Sequence Data
  • O Antigens
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification
  • Polysaccharides, Bacterial / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Carbon Isotopes
  • Glycerophosphates
  • O Antigens
  • Oligosaccharides
  • Polysaccharides, Bacterial