Antigenic bacterial polysaccharides. 24. The structure of the O-specific polysaccharide chain of Salmonella arizonae 063 (Arizona 08) lipopolysaccharide

The O-specific polysaccharide chain of the Salmonella arizonae O63 lipopolysaccharide is composed of D-glucose, D-galactose, N-acetyl-D-galactosamine, and 3-acetamido-3,6-dideoxy-D-galactose (Fuc3NAc) residues in the ratio 1:1:2:1. On the basis of methylation analysis and calculations of 13C-NMR-spectra of the polysaccharide and of the product of its selective cleavage with anhydrous hydrogen fluoride, the linear polymer lacking 3-acetamido-3,6-dideoxygalactose, it was concluded that the polysaccharide has the following structure: (Formula: see text).     

Antigenic bacterial polysaccharides. 13. The structure of the O-specific polysaccharide chain of the lipopolysaccharide from Pseudomonas cepacia strain IMV 4137

On mild acid degradation of a lipopolysaccharide from Pseudomonas cepacia strain IMV 4137, a serologically active O-specific polysaccharide was obtained and shown to contain L-rhamnose and D-galactose. According to 1H- and 13C-NMR data as well as methylation analysis, the polysaccharide is made up of disaccharide repeating units of the following structure:----2)-alpha-L-Rhap-(1----4)-alpha-D-Galp-(1----.     

Antigenic polysaccharides of bacteria. 31. The structure of the O-specific polysaccharide chain of Pseudomonas aurantiaca IMB 31 lipopolysaccharide

The O-specific polysaccharide chain of the Pseudomonas aurantiaca IMV 31 lipopolysaccharide contains N-acetyl-L-fucosamine (FucNAc) and di-N-acetyl-D-bacillosamine (2,4-diacetamido-2,4,6-trideoxyglucose, Bac(NAc)2) in the ratio 2:1. On the basis of methylation, solvolysis with anhydrous hydrogen fluoride, and computer-assisted analysis of 13C-NMR spectrum, it was concluded that the trisaccharide repeating unit of the polysaccharide possesses the following structure: structure: ----3)-beta-D-Bac(NAc)2-(1----3)-alpha-L-FucNAc-(1----3)-alpha-L- FucNAc-(1----.     

Antigenic polysaccharides of bacteria. 33. The structure of O-specific polysaccharide chain of lipopolysaccharide from Pseudomonas cepacia serotype 6

On mild acid degradation of the Pseudomonas cepacia serotype 6 lipopolysaccharide, the O-specific polysaccharide was obtained, which contains D-mannose and D-galactose residues in the ratio approximately 1:1, as well as O-acetyl groups. On the basis of 1H and 13C NMR analysis, calculation of specific optical rotation, and methylation, it was concluded that the polysaccharide possesses the following structure: (formula; see text) Regularities in glycosidation effects in 13C NMR spectra of 1,3-linked disaccharides containing furanoside residues are discussed.     

Antigenic polysaccharides of bacteria. 22. Structure of the O-specific polysaccharide chain of Proteus hauseri lipopolysaccharide

The following structure of the repeating unit of the Proteus hauseri O-specific polysaccharide was established on the basis of monosaccharide composition and 13C NMR data of the polysaccharide and products of its Smith degradation and partial cleavage with hydrogen fluoride: (Formula: see text).     

Antigenic polysaccharides of bacteria. 17. The structure of O-specific polysaccharide chain of Pseudomonas aeruginosa X (Meitert) lipopolysaccharide

O-Specific polysaccharide composed of L-rhamnose and 2-acetamido-2-deoxy-D-mannose was obtained on mild acid degradation of P. aeruginosa X (Meitert classification) lipopolysaccharide. On the basis of non-destructive analis using 1H, 13C NMR spectroscopy and Klyne's rule calculation, as well as chemical methods (acid hydrolysis, methylation, Smith degradation), it was established that the polysaccharide is built up of disaccharide repeating units of the following structure: ----4)-alpha-L-Rha-(1----3)-beta-D-ManNAc-(1----.     

Antigenic polysaccharides of bacteria. 16. The structure of O-specific polysaccharide chain of Pseudomonas aeruginosa 025 (Wokatsch) lipopolysaccharide

O-Specific polysaccharide built up of trisaccharide repeating units containing 3-acetamidino-2-acetamido-2,3-dideoxy-D-mannuronic acid (ManNAcAmA), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid (Man(NAc)2A), N-acetyl-D-fucosamine (FucNAc), and O-acetyl group was obtained on mild acid hydrolysis of P. aeruginosa O25 (Wokatsch classification) lipopolysaccharide. Basing on de-O-acetylation of polysaccharide with aqueous triethylamine accompanied by hydrolysis of acetamidino group to acetamido group, as well as on the 1H and 13C NMR data, the following structure of the repeating unit of the polysaccharide was established: (Formula: see text) P. aeruginosa O25 polysaccharide has the same carbohydrate skeleton as that of P. aeruginosa O3a,b (Lányi classification) and differs from the latter only by the presence of the O-acetyl group at position 4 of N-acetylfucosamine.     

Antigenic bacterial polysaccharides. 14. Structure of the O-specific polysaccharide chain of a lipopolysaccharide from Pseudomonas aeruginosa (Lányi)

The lipopolysaccharide from Pseudomonas aeruginosa O12 (Lányi classification) gave on mild acid hydrolysis an O-specific polysaccharide built of D-ribose and N-acetyl-D-galactosamine. The disaccharide structure----4)-alpha-GalNAcp-(1----2)-beta-Ribf-(1----for the repeating unit of the polysaccharide was established by nondestructive way involving full interpretation of its 1H- and 13C-NMR-spectra, using homonuclear and selective heteronuclear 13C[1H] double resonances.     

Antigenic bacterial polysaccharides. 36. A study of the structure of the O-specific polysaccharide chain of the lipopolysaccharide of Pseudomonas fluorescens IMV 2763 (biostrain G)

Chemical and serological characterization of the Pseudomonas fluorescens IMV 2763 (biovar G) lipopolysaccharide was carried out. The O-specific polysaccharide chain of the lipopolysaccharide is composed of D-mannose, 6-deoxy-L-talose, N-acetyl-D-galactosamine and O-acetyl groups in the ratio of approximately 2:1:1:1. The polysaccharide is branched and a half of residues of 6-deoxytalose and monosubstituted mannose carry O-acetyl groups. On the basis of methylation, partial acid hydrolysis and 13C NMR analysis it was concluded that the repeating unit of the polysaccharide has the following structure: (formula; see text)     

Antigenic bacterial polysaccharides. 29. The structure of the polysaccharide chain of Pseudomonas holci 8300 (serogroup I) lipopolysaccharide

The Pseudomonas holci 8300 lipopolysaccharide has an O-specific polysaccharide chain, containing L-rhamnose and 3-acetamido-3-deoxy-D-fucose residues in the ratio 4:1. On the basis of methylation, Smith degradation, and 1H- and 13C-NMR spectroscopy data, it was concluded that the polysaccharide is built up of pentasaccharide units of A and B types in the ratio approximately 2.5:1. In some stretches of the polysaccharide, minor B units form rather long chains, and in the others they alternate with predominant A units. (formula; see text)     

The structure of O-specific polysaccharide chain of Pseudomonas fluorescens lipopolysaccharide

An O-specific polysaccharide, containing 6-deoxy-L-talose (6dTal), N-acetyl-D-fucosamine (FucNAc), 3-amino-3,6-dideoxy-D-glucose with an unidentified N-acyl substituent (Qui3NR), and O-acetyl groups, was obtained on mild acid degradation of a Pseudomonas fluorescens strain 361 lipopolysaccharide. On the basis of O-deacetylation, acid hydrolysis, methylation, selective solvolysis with anhydrous hydrogen fluoride, and 13C NMR analysis, the polysaccharide is built up of trisaccharide repeating units of the following structure: (Formula: see text).     

Antigenic polysaccharides of bacteria. 25. Structure of the O-specific polysaccharide chain of Pseudomonas cepacia 673/2 lipopolysaccharide containing L-glycero-D-manno-heptose

O-Specific polysaccharide, consisting of D-rhamnose and L-glycero-D-manno-heptose (LD-Hep) in a 2 : 1 ratio, was obtained on the mild acid degradation of the Pseudomonas cepacia IMV 673/2 lipopolysaccharide; monosaccharide LD-Hep has not previously been found in O-specific chains of lipopolysaccharides. On the basis of methylation and 13C-NMR data, it was concluded that the polysaccharide is composed of trisaccharide repeating units having the following structure: ----3)-alpha-D-Rha-(1----3)-alpha-D-Rha-(1----2)-alpha-LD-Hep-(1----     

Antigenic bacterial polysaccharides. 30. The structure of the polysaccharide chain of lipopolysaccharide of Pseudomonas syringae pv. syringae 281 (serogroup I)

Anomeric methyl 3-O-(D-mannopyranosyl- and L-rhamnopyranosyl)-beta-D-talopyranosides were synthesised by the stereoselective 1,2-cis- and 1,2-trans manno- and rhamnosylation of methyl 2,4,6-tri-O-acetyl-beta-D-talopyranoside, which has been prepared from methyl beta-D-galactopyranoside by a synthetic scheme including conversion of the C2 configuration. From 13C-NMR spectra of the disaccharides obtained the spectral alpha- and beta-effects of O3-glycosylation of talopyranose were determined.     

The structure of the O-specific polysaccharide chain of the Shewanella algae BrY lipopolysaccharide

An acidic O-specific polysaccharide was obtained by mild acid degradation of the Shewanella algae strain BrY lipopolysaccharide and was found to contain L-rhamnose, 2-acetamido-4-[D-3-hydroxybutyramido)]-2,4,6-trideoxy-D-glucose (D-BacNAc4NHbu), and 2-amino-2,6-dideoxy-L-galactose, N-acylated by the 4-carboxyl group of L-malic acid (L-malyl-(4-->2)-alpha-L-FucN) in the ratio 2:1:1. 1H and 13C NMR spectroscopy was applied to the intact polysaccharide, and the following structure of the repeating unit was established:-3)-alpha-D-BacNAc4NHbu-(1-->3)-alpha-L-Rha-(1-->2)-alpha-L-Rha-(1-->2)-L-malyl-(4-->2)-alpha-L-FucN-(1-. The repeating unit includes linkage via the residue of malic acid, reported here for the first time as a component of bacterial polysaccharides.     

The structure of the O-specific polysaccharide chain of Proteus penneri strain 16 lipopolysaccharide

O-Specific polysaccharide was obtained by mild acid degradation of Proteus penneri strain 16 lipopolysaccharide and found to contain D-glucose, D-glucuronic acid, 2-acetamido-2-deoxy-D-glucose, and 3,6-dideoxy-3-[(R)-3-hydroxybutyramido]- D-galactose in the ratio of 2:1:1:1 as well as a small proportion of O-acetyl groups. On the basis of one-dimensional 1H-NMR13C-NMR and NOE spectroscopy, two-dimensional homonuclear-shift-correlated spectroscopy with one-step and two-step relayed coherence transfer and heteronuclear 1H/13C NMR shift-correlated spectroscopy, it was concluded that the O-specific polysaccharide of P. penneri strain 16 has the following structure: (formula; see text) This structure was confirmed by methylation analysis and structural analysis of a linear tetrasaccharide fragment prepared by cleavage of the polysaccharide with anhydrous hydrogen fluoride followed by conversion of the alpha-tetrosyl fluoride obtained in to the corresponding free oligosaccharide and alditol. O-Acetyl groups were tentatively located at position 3 of the glucuronic acid residue and at position 4 of the 6-substituted glucose residue, the degree of acetylation being less than 20% of the total. Cross-reactions of P. penneri strain 16 anti-(O-specific polysaccharide) antiserum with lipopolysaccharides from several other Proteus strains and the role of 3,6-dideoxy-3-(R)-3-hydroxybutyramido-D-galactose in the serological specificity of P. penneri strain 16 are discussed.     

Antigenic bacterial polysaccharides. 28. The structure of the O-specific lipopolysaccharide chain of Pseudomonas syringae pv. atrofaciens K-1025 and Pseudomonas holci 90a (serogroup II)

Lipopolysaccharides of serologically related strains of Pseudomonas syringae pv. atrofaciens K-1025 and Pseudomonas holci 90a possess the identical O-specific polysaccharide chains, representing a homopolymer of D-rhamnose. On the basis of methylation, partial and complete Smith degradation, and analysis by 1H- and 13C-NMR-spectroscopy, it was concluded that the repeating unit of the polysaccharide is a branched pentasaccharide of the following structure: (formula; see text)     

The structure of the O-specific polysaccharide chain of the lipopolysaccharide of Yersinia pseudotuberculosis serovar VII

An O-specific polysaccharide of Yersinia pseudotuberculosis serovar VII has been isolated and characterized. The polysaccharide consists of colitose, D-glucose and 2-acetamido-2-deoxy-D-galactose in the ratio 1 : 2 : 2. From the results of methylation analysis, partial acid hydrolysis, 1H and 13C NMR spectroscopy the structure of the repeating unit of the O-specific polysaccharide is deduced as follows:     

Somatic antigens of the Brucella genus. The structure of the O-specific polysaccharide chain of Brucella melitensis lipopolysaccharide

The phenol-phase soluble antigenic lipopolysaccharide was isolated from Brucella melitensis, strain 565, by the routine phenol/water procedure followed by chromatography on Sepharose 4B. After mild acid hydrolysis and chromatography on Sephadex G-50, the lipopolysaccharide yielded a linear O-specific polysaccharide built up from 1,2-linked 4,6-dideoxy-4-formamido-alpha-D-mannopyranosyl units. The structure of the polysaccharide was deduced mainly from the nuclear magnetic resonance and methylation analyses. The phenol-soluble lipopolysaccharide, isolated from commercial vaccine strain B. abortus 19-BA, on mild hydrolysis afforded material, 13C and 1H-NMR spectra of which were identical to those of the O-specific polysaccharide from B. melitensis 565.     

The structure of O-specific polysaccharide chains of lipopolysaccharides from Citrobacter 032 and Salmonella arizonae 064 (Arizona 29)

On the basis of acid hydrolysis, methylation, Smith degradation, selective cleavage with anhydrous hydrogen fluoride, and 13C NMR analysis, the repeating unit of the O-specific polysaccharide of Citrobacter O32 was concluded to have the following structure: (Formula: see text). The repeating unit of the Salmonella arizonae O64 O-specific polysaccharide has the same structure lacking the O-acetyl group.     

Structure of the O-specific polysaccharide chain of Yersinia aldovae lipopolysaccharide]

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].