4-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-3-deoxy-D-manno-2-octulosonic acid, a constituent of lipopolysaccharides of the genus Pectinatus.
A disaccharide containing GlcN and 3-deoxy-D-manno-2-octulosonic acid (Kdo) was detected after acidic methanolysis and peracetylation of hydrofluoric-acid-treated smooth-type and rough-type lipopolysaccharide of Pectinatus cerevisiiphilus and Pectinatus frisingensis, which are strictly anaerobic bacteria capable of growing in packaged beer. The disaccharide was also found in alkali-treated lipopolysaccharide, but was not directly detectable from intact lipopolysaccharide. This suggested that the disaccharide carried a phosphate residue. The position of this phosphate was shown, by GLC/MS of appropriately degraded and derivatized samples, to be O6 of the GlcN. Methylation analysis of the purified disaccharide revealed that GlcN was linked to position 4 of Kdo. The acetylated derivative of the disaccharide was isolated in pure form, and, by 1H-NMR and 13C-NMR spectroscopy, it was confirmed to possess the structure alpha-D-GlcpN-(1'-->4)-Kdo. In the lipopolysaccharide the amino group of GlcN is free.
Helander
I M
IM
Department of Molecular Bacteriology, National Public Health Institute, Helsinki, Finland.
Moll
H
H
Zähringer
U
U
D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D004187:Disaccharides / Q000032:analysis*; D006089:Gram-Negative Anaerobic Bacteria / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry; D013400:Sugar Acids / Q000032:analysis*; D014316:Tritium
D002247:Carbon Isotopes; D004187:Disaccharides; D008070:Lipopolysaccharides; D013400:Sugar Acids; D014316:Tritium; D010504:Periodic Acid; C080854:4-O-(2-amino-2-deoxy-alpha-glucopyranosyl)-3-deoxy-manno-2-octulosonic acid