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1. (Article ID: 1)
 
Severn WB, Richards JC
The acidic specific capsular polysaccharide of Rhodococcus equi serotype 3. Structural elucidation and stereochemical analysis of the lactate ether and pyruvate acetal substituents
Canadian Journal of Chemistry 70 (1992) 2664-2676
 

The specific capsular polysaccharide produced by Rhodococcus equi serotype 3 was found to be a high-molecularweight acidic polymer composed of D-glucose, D-galactose, D-glucuronic acid, 4-O-[(S)-1-carboxyethyll-D-mannose, and pyruvic acid in equal molar proportions. Structural analysis, employing a combination of chemical and nuclear magnetic resonance techniques, established that the polysaccharide is composed of linear repeating tetrasaccharide units [structure], in which (R)-1-carboxyethylidene groups bridge the O-2 and O-3 positions of the β-D-glucuronic acid residues. The 1H and 13C NMR resonances of the native and depyruvulated serotype 3 polysaccharides were fully assigned by homo- and heteronuclear chemical shift correlation methods. The absolute configurations of the lactate-substituted mannopyranosyl residues and the pyruvate acetals were determined from 1H-1H NOE measurements on the intact polysaccharide. Unequivocal determination of the absolute chirality of the 4-O-[(S)-1-carboxyethyll-β-D-mannopyranoseresidues was achieved by 1H-1H NOE measurements on an acetylated lactone derivative of the glycose.

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2. (Article ID: 2)
 
Horton D, Mols O, Walaszek Z, Wernau WC
Structural and biosynthetic studies on xanthan by 13C-n.m.r. spectroscopy
Carbohydrate Research 141(2) (1985) 340-346
 

no abstract

xanthan, 13C-NMR

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3. (Article ID: 3)
 
Bernabé M, Jiménez-Barbero J, Gil-Serrano AM, Gonzalez-Jimenez I, Mateo PT, Megias M
Solution structure of the trisaccharide and hexasaccharide fragments of the O-antigen of the lipopolysaccharide of Rhizobium tropici CIAT899
Carbohydrate Research 279 (1995) 339-352
 

Lipopolysaccharide, NMR, molecular modelling, conformation, AMBER force field

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4. (Article ID: 4)
 
Bernhard F, Schullerus D, Bellemann P, Nimtz M, Coplin DL, Geider K
Genetic transfer of amylovoran and stewartan synthesis between Erwinia amylovora and Erwinia stewartii
Microbiology 142 (1996) 1087-1096
 

DNA fragments with ams genes of Erwinia amylovora and cps genes of Erwinia stewartii were transferred to exopolysaccharide (EPS)-deficient mutants of the other species. The resulting EPSs were characterized by sensitivity to EPS-dependent bacteriophages, staining with amylovoran-specific fluorescein-isothiocyanate-labelled lectin and chemical techniques, such as determination of the sugar composition and methylation analysis in order to distinguish between amylovoran and stewartan. Degradation by the stewartan-dependent phage phi-K9 was used to detect stewartan production, and staining with a lectin from Abrus precatorius detected amylovoran capsules. The patterns of sugar linkages were determined by methylation analysis. Stewartan contained a significantly higher glucose to galactose ratio than amylovoran and produced a characteristic signal from 6-linked glucose residues. By these criteria, most E. stewartii cps mutants displayed exclusively amylovoran synthesis when complemented with the E. stewartii cps genes produced stewartan. The complementation to an EPS-positive phenotype may require most genes of the ams or the cps operon. An exception was an E. stewartii cpsK mutant that made predominantly stewartan when complemented with the ams cosmid. IR spectra showed that both amylovoran and stewartan were acylated when synthetized in E. amylovora, but not in E. stewartii. The amylovoran-producing E. stewartii merodiploids regained virulence to corn seedlings when mucoidy was restored by the ams cluster, but the stewartan-producing E. amylovora ams-/cps+ strains were weakly virulent on pear slices and avirulent on apple seedlings.

amylovoran, biosynthesis, complementation, Erwinia, Erwinia amylovora, fireblight, genetic, Stewart's wilt, stewartan, synthesis, transfer, transgenic bacteria

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5. (Article ID: 5)
 
Bernlind C, Oscarson S
Synthesis of L-glycero-D-manno-heptopyranose-containing oligosaccharide structures found in lipopolysaccharides from Haemophilus influenzae
Carbohydrate Research 297(3) (1997) 251-260
 

Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-galactopyranosyl)-(1→2)-O- (L-glycero-α-D-manno-heptopyranosyl)-(1→2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1→3)-L-glycero-α-D-manno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-α-D-manno-heptopyranosyl)-(1→2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1→3)-L-glycero-α-D-manno-heptopyranoside (17), 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-glucopyranosyl)-(1→4)- O-(β-D-glucopyranosyl)-(1→4)-L-glycero-α-D-manno-heptopyrano side (5), and 2-(4-trifluoro-acetamidophenyl)ethyl O-(β-D-galactopyranosyl)-(1→4)-O-(β-D-glucopyranosyl)-(1→4)- L-glycero-α-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae

Lipopolysaccharide, synthesis, antigen, carbohydrates, Haemophilus, Haemophilus influenzae, heptopyranose, L-glycero-D-manno-heptose, lipopolysaccharides, LPS, oligosaccharide, oligosaccharide structure, structure

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6. (Article ID: 6)
 
Bernlind C, Oscarson S
Synthesis of a branched heptose- and Kdo-containing common tetrasaccharide core structure of Haemophilus influenzae lipopolysaccharides via 1,6-anhydro-L-glycero-b-D-manno- heptopyranose intermediate
Journal of Organic Chemistry 63(22) (1998) 7780-7788
 

Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-galactopyranosyl)-(1→2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1→2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1→3)-L-glycero-α-D-manno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-α-D-manno-heptopyranosyl)-(1→2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1→3)-L-glycero-α-D-manno-heptopyranoside (17), 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-glucopyranosyl)-(1→4)-O-(β-D-glucopyranosyl)-(1→4)-L-glycero-α-D-manno-heptopyrano side (5), and 2-(4-trifluoro-acetamidophenyl)ethyl O-(β-D-galactopyranosyl)-(1→4)-O-(β-D-glucopyranosyl)-(1→4)-L-glycero-α-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae

Lipopolysaccharide, synthesis, Haemophilus, Haemophilus influenzae, heptopyranose, lipopolysaccharides, structure, branched, common, core, heptose, intermediate, tetrasaccharide

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7. (Article ID: 7)
 
Bernlind C, Bennett S, Oscarson S
Synthesis of a D,D- and L,D-heptose-containing hexasaccharide corresponding to a structure from Haemophilus ducreyi lipopolysaccharides
Tetrahedron, Asymmetry 11(2) (2000) 481-492
 

The synthesis of a linear hexasaccharide, 2-(4-trifluoroacetamidophenyl)ethyl (β-D-galactopyranosyl)-(1-4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-(β-D-galactopyranosyl)-(1-4)-(D-glycero-α-D-manno-heptopyranosyl)-(1-6)-(β-D-glucopyranosyl)-(1-4)-L-glycero-α-D-manno-heptopyranoside, corresponding to a structure found in Haemophilus ducreyi LPS, is described. A Barbier reaction between benzyloxymethyl chloride and a properly protected 6-aldo-1-thio-mannopyranoside yielded both the D,D- and the L,D-heptopyranoside (2 and 3, ratio 2:3), which were separated and both used in the synthesis. p-Methoxybenzyl and chloroacetyl groups were employed as temporary protecting groups, selectively removed in the presence of the persistent benzyl, acetyl, benzoyl and isopropylidene groups by treatment with DDQ/H2O and hydrazine dithiocarbonate, respectively. Thioglycosides were utilised as donors throughout using either NIS/TfOH or DMTST as promoters. The introduction of the spacer into thioglycoside 5 was high-yielding (95%) but with low stereoselectivity (alfa:beta 5:3). All other glycosylations are completely stereoselective. The target hexasaccharide is obtained via a 3+3 block approach with the yield in the final NIS/TfOH-promoted coupling between an N,N-diacetyl-trisaccharide thioglycosyl donor 20 and a 400-OH trisaccharide acceptor 13 being 75%

Lipopolysaccharide, synthesis, Haemophilus, lipopolysaccharides, structure, Haemophilus ducreyi, hexasaccharide

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8. (Article ID: 8)
 
Berrington AW, Tan YC, Srikhanta Y, Kuipers B, van der LP, Peak IR, Jennings MP
Phase variation in meningococcal lipooligosaccharide biosynthesis genes
FEMS Immunology and Medical Microbiology 34(4) (2002) 267-275
 

Neisseria meningitidis expresses a range of lipooligosaccharide (LOS) structures, comprising of at least 13 immunotypes (ITs). Meningococcal LOS is subject to phase variation of its terminal structures allowing switching between ITs, which is proposed to have functional significance in disease. The objectives of this study were to investigate the repertoire of structures that can be expressed in clinical isolates, and to examine the role of phase-variable expression of LOS genes during invasive disease. Southern blotting was used to detect the presence of LOS biosynthetic genes in two collections of meningococci, a global set of strains previously assigned to lineages of greater or lesser virulence, and a collection of local clinical isolates which included paired throat and blood isolates from individual patients. Where the phase-variable genes lgtA, lgtC or lgtG were identified, they were amplified by PCR and the homopolymeric tracts, responsible for their phase-variable expression, were sequenced. The results revealed great potential for variation between alternate LOS structures in the isolates studied, with most strains capable of expressing several alternative terminal structures. The structures predicted to be currently expressed by the genotype of the strains agreed well with conventional immunotyping. No correlation was observed between the structural repertoire and virulence of the isolate. Based on the potential for LOS phase variation in the clinical collection and observations with the paired patient isolates, our data suggest that phase variation of LOS structures is not required for translocation between distinct compartments in the host

Lipopolysaccharide, biosynthesis, structure, Meningococcus, Phase variation, Lipooligosaccharide, Pathogenesis, Neisseria meningitidis, alternative, Bacterial Proteins, biosynthetic, blood, blotting, chemistry, clinical, correlation, disease, expression, functional, gene, Gene Expression Regulation, Bacterial, genetics, genotype, growth & development, host, human, immunotype, immunotyping, invasive, isolate, LOS, meningococcal, Meningococcal Infections, meningococci, metabolism, microbiology, Neisseria, pathogenicity, PCR, phase, phenotype, polymerase chain reaction, potential, role, Sequence Analysis, DNA, significance, strain, structural, Support, Non-U.S.Gov't, terminal, tract, translocation, variation, Variation (Genetics), virulence

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9. (Article ID: 9)
 
Beynon LM, Richards JC, Perry MB, Kniskern PJ
Characterization of the capsular antigen of Streptococcus pneumoniae serotype 35B
Canadian Journal of Chemistry 73 (1995) 41-48
 

The specific capsular antigen of Streptococcus pneumoniae serotype 35B was shown by a combination of 2D NMR methods and mass spectrometric and classical carbohydarate chemical techniques to be a high molecular weihgt polymer containing D-galactose, D-glucose, 2-acetamido-2deoxy-D-galactose, and ribitol (2:1:1:1). The polysaccharide repeating unit is polymerized through phosphate diester linkages to give the structure {structure}. Seventy persent of the bDGalf residues glycosidically linked to the ribitol units carry an O-acetyl sustituent.

antigen, structure, capsular, characterization, K-antigen, polysaccharide, serotype, Streptococcus, Streptococcus pneumoniae

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10. (Article ID: 10)
 
Beynon LM, Cox AD, Taylor CJ, Wilkinson SG, Perry MB
Characterization of a lipopolysaccharide containing two different trisaccharide repeating units from Burkholderia cepacia serotype E (O2)
Carbohydrate Research 272 (1995) 231-239
 

The O antigen of the lipopolysaccharide of Burkholderia cepacia serotype E (O2) was shown by a combination of methylation analysis, partial hydrolysis, NMR, and mass spectrometric methods to be a high molecular weight polysaccharide composed of two different trisaccharide repeating units in the ratio 2:1. The major trisaccharide component is composed of two α-D-mannopyranosyl and one β-D-galactopyranosyl residues with the structure, [→2)-α-D-Manp-(1→2)-α-D-Manp-(1→4)-β-D-Galp-(1→]n The minor trisaccharide component is a D-mannan composed of two α- and one β-D-mannopyranosyl residues with the structure, [→2)-α-D-Manp-(1→2)-α-D-Manp-(1→3)-β-D-Manp-(1→]n

Lipopolysaccharide, LPS, structure, characterization, serotype, methylation analysis, 2D NMR (COSY, NOESY) experiments, GCL-MC of alditol acetates, FASBMS, Burkholderia, Burkholderia cepacia, D-mannose, O-antigen, repeating unit, trisaccharide

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