The Chemical Structure of the Lipid A Component of Lipopolysaccharides from Vibrio cholerae

Abstract

The chemical structure of the lipid A component of the lipopolysaccharide from Vibrio cholerae 95R was studied. After sequential degradation a reduced D-glucosamine disaccharide was isolated from lipid A and, after permethylation, shown by combined gas-liquid chromatography/mass spectrometry to be beta 1,6-linked. The disaccharide is substituted with a phosphate group, ester-bound to the non-reducing glucosamine (GlcN) residue and a pyrophosphorylethanolamine group (PP-Etn) linked to C-1 of the reducing glucosamine residue. This backbone structure is shown in the following formula: P-GlcN(beta 1-6)GlcN-1-PP-Etn. The amino groups of the glucosamine disaccharide are substituted by D-3-hydroxytetradecanoic acid; tetradecanoic, hexadecanoic and a D-3-O-(D-3-hydroxydodecanoyl)-dodecanoic acid residue are linked to hydroxyl groups. A similar fatty acid composition was detected in lipopolysaccharides from Inaba, Ogawa and NAG strains of V. cholerae.