title: 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.
abstract: 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.
authors.affiliation: Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, F.R.G.
authors.forename: W
authors.initials: W
authors.lastname: Kaca
authors.forename: J
authors.initials: J
authors.lastname: de Jongh-Leuvenink
authors.forename: U
authors.initials: U
authors.lastname: Zähringer
authors.forename: E T
authors.initials: ET
authors.lastname: Rietschel
authors.forename: H
authors.initials: H
authors.lastname: Brade
authors.forename: J
authors.initials: J
authors.lastname: Verhoef
authors.forename: V
authors.initials: V
authors.lastname: Sinnwell
mesh_terms: 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
chemical_list: 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