Alpha-2----4-interlinked 3-deoxy-D-manno-octulosonic acid disaccharide. A common constituent of enterobacterial lipopolysaccharides.
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.
D002849:Chromatography, Gas; D004187:Disaccharides / Q000032:analysis*; D004755:Enterobacteriaceae / Q000032:analysis*; D008401:Gas Chromatography-Mass Spectrometry; D008070:Lipopolysaccharides / Q000032:analysis*; D011135:Polysaccharides, Bacterial / Q000032:analysis*; D013400:Sugar Acids / Q000032:analysis*
D004187:Disaccharides; D008070:Lipopolysaccharides; D011135:Polysaccharides, Bacterial; D013400:Sugar Acids; C002532:2-keto-3-deoxyoctonate; C043922:3-deoxyoctulosonic acid-(alpha-2-4)-3-deoxyoctulosonic acid