Alpha-2----4-interlinked 3-deoxy-D-manno-octulosonic acid disaccharide. A common constituent of enterobacterial lipopolysaccharides

Eur J Biochem. 1984 Dec 3;145(2):231-6. doi: 10.1111/j.1432-1033.1984.tb08543.x.

Abstract

After mild acid hydrolysis, a disaccharide of 3-deoxy-D-manno-octulosonic acid (dOclA) was obtained from Re-mutant lipopolysaccharide of Salmonella minnesota, Salmonella godesberg, Proteus mirabilis, and Escherichia coli, and from the lipopolysaccharide of an S. minnesota Rb2 mutant. Combined gas-liquid chromatography/mass spectrometry of the reduced and permethylated derivatives indicated that the disaccharide is interlinked by a 2----4-glycosidic bond in all lipopolysaccharides tested. In addition, it was shown by gas-liquid chromatography of appropriate synthetic standards and a previously characterized alpha 2----4-linked dOclA disaccharide (derived from lipopolysaccharide of S. godesberg) that the non-reducing dOclA residue possesses the alpha configuration. In the case of lipopolysaccharide of S. minnesota Rb2 mutant, this result, together with earlier findings, suggests that it contains a linear dOclA trisaccharide of the sequence dOclA(alpha 2-4)dOclA. The results show that a dOclA(alpha 2-4)dOclA disaccharide represents a common architectural principle in enterobacterial lipopolysaccharides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Gas
  • Disaccharides / analysis*
  • Enterobacteriaceae / analysis*
  • Gas Chromatography-Mass Spectrometry
  • Lipopolysaccharides / analysis*
  • Polysaccharides, Bacterial / analysis*
  • Sugar Acids / analysis*

Substances

  • Disaccharides
  • Lipopolysaccharides
  • Polysaccharides, Bacterial
  • Sugar Acids
  • 2-keto-3-deoxyoctonate
  • 3-deoxyoctulosonic acid-(alpha-2-4)-3-deoxyoctulosonic acid