Isolation and chemical analysis of 7-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-L-glycero-D-manno-heptose as a constituent of the lipopolysaccharides of the UDP-galactose epimerase-less mutant J-5 of Escherichia coli and Vibrio cholerae.
Methyl 7-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-L-glycero-D-manno-hepto+ ++ pyranoside (1) was released from the lipopolysaccharide of the UDP-galactose epimerase-less mutant J-5 of Escherichia coli by methanolysis and isolated by high-voltage paper electrophoresis. Its chemical structure was determined by chemical analysis, deamination with nitrous acid, g.1.c.-m.s., and 1H- and 13C-n.m.r. spectroscopy performed on its acetylated derivative. The disaccharide moiety of 1 was also detected in lipopolysaccharides of Vibrio cholerae.
Kaca
W
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Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, F.R.G.
de Jongh-Leuvenink
J
J
Zähringer
U
U
Rietschel
E T
ET
Brade
H
H
Verhoef
J
J
Sinnwell
V
V
D002238:Carbohydrate Epimerases / Q000235:genetics*; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D004187:Disaccharides / Q000032:analysis*; D004926:Escherichia coli / Q000032:analysis* / Q000235:genetics; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000032:analysis; D006539:Heptoses / Q000032:analysis; D008070:Lipopolysaccharides / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009154:Mutation; D009608:Nitrous Acid; D014534:UDPglucose 4-Epimerase / Q000235:genetics*; D014734:Vibrio cholerae / Q000032:analysis* / Q000235:genetics
D004187:Disaccharides; D006539:Heptoses; D008070:Lipopolysaccharides; C026312:glycero-manno-heptose; C058143:7-O-(2-amino-2-deoxyglucopyranosyl)heptose; D002238:Carbohydrate Epimerases; D014534:UDPglucose 4-Epimerase; D005947:Glucose; D009608:Nitrous Acid