title: Structural studies of the O-specific polysaccharide of Vibrio cholerae O8 using solvolysis with triflic acid.
abstract: The O-specific polysaccharide (OPS) of Vibrio cholerae 08 was isolated by mild acid degradation of the lipopolysaccharide and studied by two-dimensional NMR spectroscopy, including NOESY and heteronuclear multiple-bond correlation (HMBC) experiments. The OPS was found to have a tetrasaccharide repeating unit with the following structure: --> 4)-beta-D-Glcp NAc3NAcylAN-(1 --> 4)-beta-D-Manp NAc3NAcAN-(1 --> 4)-alpha-L-Gulp NAc3NAcA-(1 --> 3) -beta-D-QuipNAc4NAc-(1 --> where QuiNAc4NAc is 2,4-diacetamido-2,4,6-trideoxyglucose, GlcNAc3NAcylAN is 2-acetamido-3-(N-formyl-L-alanyl)amino-2,3-dideoxyglucuronamide, ManNAc3NAcAN is 2,3-diacetamido-2,3-dideoxymannuronamide, and GulNAc3NAcA is 2,3-diacetamido-2,3-dideoxyguluronic acid. The OPS was stable towards acid hydrolysis and solvolysis with anhydrous hydrogen fluoride, but could be cleaved selectively with trifluoromethanesulfonic (triflic) acid by the glycosidic linkages of beta-QuiNAc4NAc and alpha-GulNAc3NAcA. The structures of the oligosaccharides obtained that were elucidated by electrospray ionization (ESI) MS and NMR spectroscopy, confirmed the OPS structure.
authors.affiliation: Karolinska Institute, Clinical Research Centre, Huddinge University Hospital, Sweden.
authors.forename: N A
authors.initials: NA
authors.lastname: Kocharova
authors.forename: A V
authors.initials: AV
authors.lastname: Perepelov
authors.forename: G V
authors.initials: GV
authors.lastname: Zatonsky
authors.forename: A S
authors.initials: AS
authors.lastname: Shashkov
authors.forename: Y A
authors.initials: YA
authors.lastname: Knirel
authors.forename: P E
authors.initials: PE
authors.lastname: Jansson
authors.forename: A
authors.initials: A
authors.lastname: Weintraub
mesh_terms: D000942:Antigens, Bacterial / Q000737:chemistry / Q000302:isolation & purification; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D008698:Mesylates; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D019081:O Antigens / Q000737:chemistry* / Q000302:isolation & purification; D011135:Polysaccharides, Bacterial / Q000276:immunology; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D014734:Vibrio cholerae / Q000276:immunology*
chemical_list: D000942:Antigens, Bacterial; D008698:Mesylates; D019081:O Antigens; D011135:Polysaccharides, Bacterial; D012997:Solvents; C012077:trifluoromethanesulfonic acid