RESUMO
Structure of the O-specific polysaccharide chain of the lipopolysaccharide (LPS) of Shewanella japonica KMM 3601 was elucidated. The initial and O-deacylated LPS as well as a trisaccharide representing the O-deacetylated repeating unit of the O-specific polysaccharide were studied by sugar analysis along with 1H and 13C NMR spectroscopy. The polysaccharide was found to contain a rare higher sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-talo-non-2-ulosonic acid (a derivative of 4-epilegionaminic acid, 4eLeg). The following structure of the trisaccharide repeating unit was established: â4)-α-4eLegp5Ac7Ac-(2â4)-ß-D-GlcpA3Ac-(1â3)-ß-D-GalpNAc-(1â.
Assuntos
Antígenos O/química , Shewanella/química , Sequência de Carboidratos , Dados de Sequência Molecular , Ressonância Magnética Nuclear Biomolecular , Shewanella/imunologia , Açúcares Ácidos/análiseRESUMO
The impact of Pseudoalteromonas nigrifaciens KMM 156 lipopolysaccharide and its fragments on adhesion of prokaryote and eukaryote cells was studied. The lipopolysaccharide and O-specific polysaccharide identical by its structure to capsular polysaccharide lowered the number of the Yersinia pseudotuberculosis bacteria attached to sheep erythrocytes and adhesion of mouse neutrophils to plastic. The kora oligosaccharide had no effect on the processes.
Assuntos
Aderência Bacteriana/efeitos dos fármacos , Eritrócitos/metabolismo , Lipopolissacarídeos/farmacologia , Neutrófilos/fisiologia , Pseudoalteromonas/química , Yersinia pseudotuberculosis/fisiologia , Animais , Bivalves/microbiologia , Adesão Celular/efeitos dos fármacos , Trato Gastrointestinal/microbiologia , Camundongos , Antígenos O/farmacologia , Oceanos e Mares , Pseudoalteromonas/isolamento & purificação , OvinosRESUMO
A phosphorylated polysaccharide was isolated from the aqueous layer of the phenol-water extract of a non-halophilic bacterium Shewanella putrefaciens strain S29. The glycosyl phosphate linkage in the polysaccharide was split under mild acid conditions to give, after borohydride reduction, a phosphorylated oligosaccharide-alditol. On the basis of sugar analysis and 1H, 13C and 31P NMR spectroscopy, including 2D COSY, relayed COSY, rotating-frame NOE spectroscopy (ROESY), heteronuclear 13C,1H COSY, and H-detected heteronuclear 1H,31P multiple-quantum coherence (HMQC), it was concluded that the polysaccharide is built up of tetrasaccharide-phosphate repeating units having the following structure: [sequence: see text] where QuiNAc and Qui4NAc are 2-acetamido-2,6-dideoxyglucose and 4-acetamido-4,6-dideoxyglucose, respectively.
Assuntos
Bacilos Gram-Negativos Anaeróbios Facultativos/química , Hexosefosfatos , Polissacarídeos Bacterianos/química , Sequência de Carboidratos , Isótopos de Carbono , Cromatografia Gasosa-Espectrometria de Massas , Dados de Sequência Molecular , Ressonância Magnética Nuclear Biomolecular , Oligossacarídeos/química , FosforilaçãoRESUMO
Mild hydrolysis of the lipopolysaccharide (LPS) from Yersinia kristensenii serovar O:25.35 with acid afforded the O-specific polysaccharide (PS) which contained D-glucose, D-galactose, 2-acetamido-2,6-dideoxy-L-galactose, 2-acetamido-2-deoxy-D-glucose, glycerol, and phosphate in the ratios 3:1:1:1:1. On the basis of 31P and 13C NMR spectroscopy, hydrolysis, methylation studies, Smith degradation, and dephosphorylation, the repeating unit of PS was shown to have the following structure. [formula: see text]
Assuntos
Lipopolissacarídeos/química , Polissacarídeos Bacterianos/química , Yersinia/química , Acetilglucosamina , Sequência de Carboidratos , Fucose/análogos & derivados , Fucose/análise , Galactose/análise , Glucose/análise , Glicerol/análise , Hidrólise , Espectroscopia de Ressonância Magnética , Metilação , Dados de Sequência Molecular , Antígenos O , Fosfatos/análiseRESUMO
A capsular polysaccharide was obtained from Alteromonas nigrifaciens IAM 13010T by saline extraction. On the basis of 1H and 13C NMR spectroscopy, including one-dimensional (1D) NOE spectroscopy, 2D rotating-frame NOE spectroscopy (ROESY), and 1H-detected heteronuclear 1H,13C multiple-quantum coherence (HMQC), it was concluded that the polysaccharide contained inter alia an acidic sugar, 3-deoxy-D-manno-octulosonic acid (Kdo), and a rare amino sugar, 2-acetamido-2,6-dideoxy-L-talose (L-6dTalNAc, N-acetylpneumosamine), and has a pentasaccharide repeating unit of the following structure: [equation: see text]
Assuntos
Bactérias Aeróbias Gram-Negativas/imunologia , Hexosaminas/análise , Polissacarídeos Bacterianos/química , Configuração de Carboidratos , Sequência de Carboidratos , Bactérias Aeróbias Gram-Negativas/química , Bactérias Aeróbias Gram-Negativas/crescimento & desenvolvimento , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Oligossacarídeos/química , Oligossacarídeos/isolamento & purificação , Polissacarídeos Bacterianos/isolamento & purificação , Açúcares Ácidos/análiseRESUMO
Capsular polysaccharide (CPS) was obtained by water-saline extraction of the Alteromonas sp. CMM 155. On the basis of solvolysis with anhydrous HF and 1H- and 13C-NMR spectral data, including NOE experiments, it was concluded that the capsular polysaccharide had the following structure containing novel N-acyl-amino sugar and bacillosamine residues: --> 3)-alpha-D-GalpNAc-(1 --> 4)-alpha-L-GalApNAc(1 --> 3)- alpha-D-QuipNAc4NAc-(1 --> 3)-beta-D-Quip4NAlaAc-(1 -->
Assuntos
Cápsulas Bacterianas/química , Bactérias Aeróbias Gram-Negativas/química , Oligossacarídeos/química , Configuração de Carboidratos , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
The structure of the O-specific polysaccharide from lipopolysaccharide of Pseudoalteromonas elyakovii sp. nov. CMM 162 on the basis of NMR data, Smith degradation and methylation study was elucidated as follows:-->2)-alpha-D-Glcp-(1-->4)-beta-D-GalpNAc-(1--> 3)-alpha-D-Galp-(1-->3)-beta-D-Galp-NAc-(1-->6)-alpha-D-Glcp-(1-->.
Assuntos
Bactérias Aeróbias Gram-Negativas/química , Antígenos O/química , Sequência de Carboidratos , Bactérias Aeróbias Gram-Negativas/classificação , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
O-specific polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Pseudoalteromonas tetraodonis type strain IAM 14160(T) and studied by sugar and methylation analyses along with 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, 1H,(13)C HMQC and HMBC experiments. The polysaccharide was found to consist of hexasaccharide repeating units containing one residue each of D-Gal, D-GlcA, D-GalNAc and D-GlcNAc and two residues of 3,6-dideoxy-L-xylo-hexose (colitose, Col) and having the following structure:In common with the polysaccharides of some other bacteria, the polysaccharide studied contains a tetrasaccharide fragment alpha-Colp-(1-->2)-beta-D-Galp-(1-->3)-[alpha-Colp-(1-->4)]-beta-D-GlcpNAc, which is a colitose ('3-deoxy-L-fucose') analogue of the Lewis(b) blood group antigenic determinant.
Assuntos
Desoxiaçúcares/química , Gammaproteobacteria/química , Antígenos O/química , Configuração de Carboidratos , Sequência de Carboidratos , Gammaproteobacteria/isolamento & purificação , Espectroscopia de Ressonância Magnética , Biologia Marinha , Dados de Sequência MolecularRESUMO
An acidic extracellular polysaccharide composed of D-glucose, L-fucose, D-glucuronic acid and pyruvic acid residues has been isolated from the Mycobacterium convolutum culture fluid. On the basis of methylation analysis and 13C NMR data, the structure of the repeating unit of the polysaccharide was deduced as follows: -->3)-beta-D-Glcp-(1-->4)-beta-D-GlcpA-(1-->4)-alpha-L-Fucp- (1--> [formula: see text]
Assuntos
Mycobacterium/química , Polissacarídeos Bacterianos/química , Sequência de Carboidratos , Meios de Cultura , Fucose/análise , Glucose/análise , Glucuronatos/análise , Ácido Glucurônico , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
O-specific polysaccharide has been isolated on mild hydrolysis of lipopolysaccharide from Yersinia aldovae and shown to consist of 2-acetamido-2-deoxy-D-glucose, D-glucose, 2-acetamido-2-deoxy-D-galactose, and 3,6-dideoxy-3- [(R)-3-hydroxybutyramido]-D-galactose in molar ratio 2:2:1:1. Acid hydrolysis, methylation, solvolysis with anhydrous hydrogen fluoride, 1H and 13C NMR studies indicated the polysaccharide to be composed of hexasaccharide repeating units of the following structure: [formula see text].
Assuntos
Lipopolissacarídeos/química , Yersinia/metabolismo , Configuração de Carboidratos , Sequência de Carboidratos , Ácido Fluorídrico/química , Concentração de Íons de Hidrogênio , Hidrólise , Espectroscopia de Ressonância Magnética , Metilação , Dados de Sequência Molecular , SolventesRESUMO
An O-specific polysaccharide composed of L-rhamnose was obtained on mild acid degradation of the Yersinia rohdei lipopolysaccharide. On the basis of methylation studies and 13C NMR data, the O-specific polysaccharide is shown to be a linear L-rhamnan built up of trisaccharide repeating units of the following structure: -->3)-alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->3)-beta-L-Rh ap-(1--> The structure was confirmed by calculations with the use of the known glycosylation effect on 13C chemical shifts.
Assuntos
Polissacarídeos Bacterianos/química , Yersinia/química , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Antígenos O , Ramnose/análiseRESUMO
O-Specific polysaccharide composed of L-rhamnose and 2-acetamido-2-deoxy-D-mannose was obtained on mild acid degradation of the V. fluvialis lipopolysaccharide. On the basis of the 13C-NMR data and methylation studies, the following structure was suggested for the polysaccharide repeating unit: ----4)-alpha-L-Rhap-(1----3)-beta-D-ManpNAc-(1---- This structure was confirmed by calculations using known glycosidation effects on 13C chemical shifts.
Assuntos
Polissacarídeos Bacterianos/química , Vibrio/metabolismo , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Antígenos O , Polissacarídeos/químicaRESUMO
O-Specific polysaccharide chain of the Vibrio fluvialis lipopolysaccharide is built up of pentasaccharide repeating units, containing one N-acetyl-D-glucosamine and four L-rhamnose residues. The structure of the polysaccharide was elucidated using two-dimensional correlation 1H-NMR-spectroscopy, 13C-NMR-spectroscopy and nuclear Overhauser effect and confirmed by methylation analysis and selective cleavage of N-acetylglucosamine residues by the N-deacetylation-deamination method which yielded linear L-rhamnan representing the backbone of the polysaccharide. Thus, the repeating unit of the O-specific polysaccharide has the following structure: (formula; see text)
Assuntos
Lipopolissacarídeos/imunologia , Vibrio/imunologia , Acetilação , Antígenos de Bactérias , Sequência de Carboidratos , Hidrólise , Espectroscopia de Ressonância Magnética , Metilação , Dados de Sequência Molecular , Antígenos O , Especificidade por SubstratoRESUMO
The O-specific polysaccharide was isolated from Yersinia mollaretii strain WS 42/89 and characterized. Studies of the partial hydrolysis and methylation products and the 1H and 13C NMR spectroscopy data enabled the following structure to be proposed for the repeating unit of the polysaccharide: -->2)-beta-D-Galp-(1-->3)-alpha-D-6dGulp-(1--> The same structure was ascribed to the O-specific polysaccharide from Yersinia enterocolitica serovar O:6.31. The difference between these two O-antigens from various Yersinia species is in the absence of D-glycero-D-manno-heptose residues in the structure of the lipopolysaccharide from Y. mollaretii.
Assuntos
Antígenos O/química , Yersinia/química , Heptoses/análise , Espectroscopia de Ressonância Magnética , Metilação , Antígenos O/isolamento & purificação , Yersinia/genética , Yersinia enterocolitica/químicaRESUMO
An acidic polysaccharide from Alteromonas sp. 4MC17 is built up of trisaccharide repeating units containing D-glucose, D-mannose and D-galacturonic acid residues. On the basis of methylation studies, 1H and 13C NMR-spectroscopy data, including two-dimensional homonuclear correlation spectroscopy and nuclear Overhauser effects, the following structure was suggested for the polysaccharide repeating unit: -->4)-beta-D-Glcp-(1-->4)-beta-D-GalpA-(1-->4)-beta-D-Manp-( 1-->.
Assuntos
Bactérias Aeróbias Gram-Negativas/química , Polissacarídeos Bacterianos/química , Configuração de Carboidratos , Sequência de Carboidratos , Isótopos de Carbono , Hidrogênio , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
An acidic polysaccharide from Alteromonas macleodii 2MM6 is shown to consist of tetrasaccharide repeating units containing D-galactose, 3-O-acetyl-2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-L-guluronic acid and 3,6-dideoxy-3-(4-hydroxybutyramido)-D-galactose residues. On the basis of sugar analysis, 1H and 13C NMR-spectroscopy data including NOE and one-dimensional HOHAHA experiments, the following structure was suggested for the polysaccharide repeating unit: [formula: see text] R: -CO-CH2-CH2-CH2-OH.
Assuntos
Bactérias Aeróbias Gram-Negativas/química , Polissacarídeos Bacterianos/química , Configuração de Carboidratos , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
O-Specific polysaccharide of Vibrio fluvialis, strain AQ-0002B, is built up to pentasaccharide repeating units contained of D-mannose, 2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, D-galacturonic acid and 3-0-[(R)-1'-carboxyethyl]-L-rhamnose (rhamnoactylic acid, Rha3Lac) residues. On the basis of methylation studies, solvolysis with HF, Smith degradation, 1H and 13C NMR-spectroscopy including homo- and heteronuclear correlation spectroscopy and NOE experiments, the following structure was suggested for the polysaccharide repeating unit: [formula: see text]
Assuntos
Oligossacarídeos/química , Polissacarídeos Bacterianos/química , Vibrio/química , Configuração de Carboidratos , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Antígenos ORESUMO
An acidic capsular and an O-specific polysaccharide were isolated from the marine microorganism Alteromonas haloplanktis KMM 156. Both polysaccharides have the identical structure and are built up of tetrasaccharide repeating units, containing two residues of L-rhamnose as well as a 2-acetamido-2-deoxy-D-glucose and a 3-O-[(R)-1-carboxyethyl]-D-glucose (Glc3Lac) residue. On the basis of methylation studies, 1H- and 13C-NMR-spectroscopy including nuclear Overhauser effect and two-dimensional heteronuclear 13C/1H correlation spectroscopy, the following structure was suggested for the polysaccharide repeating unit: [formula: see text]
Assuntos
Bactérias Aeróbias Gram-Negativas/química , Polissacarídeos Bacterianos/química , Sequência de Carboidratos , Concentração de Íons de Hidrogênio , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
On the basis of acid hydrolysis, dephosphorylation, methylation, and 13C NMR spectroscopy data, the O-specific polysaccharide of Pseudoalteromonas sp. KMM 639 was shown to be a glycerophosphate-containing polymer built of repeating disaccharide units of the following structure: [formula: see text]
Assuntos
Glicerofosfatos/química , Bactérias Aeróbias Gram-Negativas/química , Lipopolissacarídeos/química , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
Immune system modulating activity of exoglycane isolated from culture media of Vibrio alginolyticus (strain 945-80) was investigated. The substance demonstrated stimulating activity on the humoral and cell immune system, potentiated phagocyte activity of macrophage and neutrophils, increased survival index of the animals infected by Gram-positive and Gram-negative bacteria.