Found 118 structures.
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1. Compound ID: 13
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1--/2-(4-trifluoroacetamidophenyl)ethyl/ |
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Structure type: oligomer
Aglycon: 2-(4-trifluoroacetamidophenyl)ethyl
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_139428,IEDB_140087,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 6
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
Journal NLM ID: 9010953Publisher: Oxford: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR
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2. Compound ID: 125
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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b-D-Galp-(1-7)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1--/lipid A/
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a-D-Glcp-(1-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_137779,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 23
Brisson J, Crawford E, Uhrin D, Khieu NH, Perry MB, Severn WB, Richards JC "The core oligosaccharide component from Mannheimia (Pasteurella) haemolytica serotype A1 lipopolysaccharide contains L-glycero-D-manno- and D-glycero-D-manno-heptoses: Analysis of the structure and conformation by high-resolution NMR spectroscopy" -
Canadian Journal of Chemistry 80 (2002) 949-963
Previous studies from our laboratory have indicated that the lipopolysaccharide (LPS) from Mannheimia haemolytica serotype A1 contains both L-glycero-D-manno-heptose and D-glycero-D-manno-heptose residues. NMR methods making use of 1D 1H selective excitation and 2D (1H, 13C) and (1H, 31P) heteronuclear experiments were used for the structural determination of the major core oligosaccharide components of the deacylated low-molecular-mass LPS obtained following sequential treatment with anhydrous hydrazine and aq KOH. The core oligosaccharide region was found to be composed of a branched octasaccharide linked to the deacylated lipid A moiety via a 3-deoxy-4-phospho-D-manno-oct-2-ulosonate residue having the structure [structure]. Heterogeneity was found to be present at several linkages. NMR methods were devised to distinguish between the diastereomeric forms of the heptose residues. Synthesized monosaccharides of L-D- and D-D-heptose were used as model compounds for analysis of the 1H and 13C NMR chemical shifts and proton coupling constants. Molecular modeling using a Monte Carlo method for conformational analysis of saccharides was used to determine the conformation of the inner core of the oligosaccharide and to establish the stereochemical relationships between the heptoses
NMR, conformation, LPS, oligosaccharide, heptose
Publication DOI: 10.1139/v02-114Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Correspondence: jim.richards@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON K1A 0R6, Canada, Agricultural Research, Department of Diseases, Upper Hutt, New Zealand, University of Edinburgh, Department of Chemistry, West Mains Road, Edinburgh EH9 3JJ, U.K
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, deacylation, ESI-MS, conformation analysis
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3. Compound ID: 126
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-4)-+ P-4)-+
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b-D-Galp-(1-7)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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a-D-Glcp-(1-6)-+ |
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Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140956,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 23
Brisson J, Crawford E, Uhrin D, Khieu NH, Perry MB, Severn WB, Richards JC "The core oligosaccharide component from Mannheimia (Pasteurella) haemolytica serotype A1 lipopolysaccharide contains L-glycero-D-manno- and D-glycero-D-manno-heptoses: Analysis of the structure and conformation by high-resolution NMR spectroscopy" -
Canadian Journal of Chemistry 80 (2002) 949-963
Previous studies from our laboratory have indicated that the lipopolysaccharide (LPS) from Mannheimia haemolytica serotype A1 contains both L-glycero-D-manno-heptose and D-glycero-D-manno-heptose residues. NMR methods making use of 1D 1H selective excitation and 2D (1H, 13C) and (1H, 31P) heteronuclear experiments were used for the structural determination of the major core oligosaccharide components of the deacylated low-molecular-mass LPS obtained following sequential treatment with anhydrous hydrazine and aq KOH. The core oligosaccharide region was found to be composed of a branched octasaccharide linked to the deacylated lipid A moiety via a 3-deoxy-4-phospho-D-manno-oct-2-ulosonate residue having the structure [structure]. Heterogeneity was found to be present at several linkages. NMR methods were devised to distinguish between the diastereomeric forms of the heptose residues. Synthesized monosaccharides of L-D- and D-D-heptose were used as model compounds for analysis of the 1H and 13C NMR chemical shifts and proton coupling constants. Molecular modeling using a Monte Carlo method for conformational analysis of saccharides was used to determine the conformation of the inner core of the oligosaccharide and to establish the stereochemical relationships between the heptoses
NMR, conformation, LPS, oligosaccharide, heptose
Publication DOI: 10.1139/v02-114Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Correspondence: jim.richards@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON K1A 0R6, Canada, Agricultural Research, Department of Diseases, Upper Hutt, New Zealand, University of Edinburgh, Department of Chemistry, West Mains Road, Edinburgh EH9 3JJ, U.K
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, deacylation, ESI-MS, conformation analysis
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4. Compound ID: 171
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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b-D-Galp-(1-7)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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a-D-Glcp-(1-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 36
Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" -
Carbohydrate Research 338(23) (2003) 2431-2447
Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.
Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains
NCBI PubMed ID: 14670707Publication DOI: 10.1016/j.carres.2003.07.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: martine.carloff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
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5. Compound ID: 282
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 75
Filiatrault MJ, Gibson BW, Schilling B, Sun SH, Munson RS, Campagnari AA "Construction and characterization of Haemophilus ducreyi lipooligosaccharide (LOS) mutants defective in expression of heptosyltransferase III and b1,4-glucosyltransferase: Identification of LOS glycoforms containing lactosamine repeats" -
Infection and Immunity 68(6) (2000) 3352-3361
To begin to understand the role of the lipooligosaccharide (LOS) molecule in chancroid infections, we constructed mutants defective in expression of glycosyltransferase genes. Pyocin lysis and immunoscreening was used to identify a LOS mutant of Haemophilus ducreyi 35000. This mutant, HD35000R, produced a LOS molecule that lacked the monoclonal antibody 3F11 epitope and migrated with an increased mobility on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). Structural studies indicated that the principal LOS glycoform contains lipid A, Kdo, and two of the three core heptose residues. HD35000R was transformed with a plasmid library of H. ducreyi 35000 DNA, and a clone producing the wild-type LOS was identified. Sequence analysis of the plasmid insert revealed one open reading frame (ORF) that encodes a protein with homology to the WaaQ (heptosyltransferase III) of Escherichia coli. A second ORF had homology to the LgtF (glucosyltransferase) of Neisseria meningitidis. Individual isogenic mutants lacking expression of the putative H. ducreyi heptosyltransferase III, the putative glucosyltransferase, and both glycosyltransferases were constructed and characterized. Each mutant was complemented with the representative wild-type genes in trans to restore expression of parental LOS and confirm the function of each enzyme. Matrix-assisted laser desorption ionization mass spectrometry and SDS-PAGE analysis identified several unique LOS glycoforms containing di-, tri-, and poly-N-acetyllactosamine repeats added to the terminal region of the main LOS branch synthesized by the heptosyltransferase III mutant. These novel H. ducreyi mutants provide important tools for studying the regulation of LOS assembly and biosynthesis
Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, expression, LOS, characterization, identification, mutant, mutants, construction, heptosyltransferase, lactosamine
NCBI PubMed ID: 10816485Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: AAC@acsu.buffalo.edu
Institutions: Department of Microbiology, Department of Medicine, Division of Infectious Diseases, and Center for Microbial Pathogenesis, University at Buffalo, Buffalo, New York 14214, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA3, and Children's Research Institute4 and Department of Molecular Virology, Immunology, and Medical Genetics,5 Ohio State University, Columbus, Ohio 43205-2696
- Article ID: 398
Tullius MV, Phillips NJ, Scheffler NK, Samuels NM, Munson JR, Hansen EJ, Stevens-Riley M, Campagnari AA, Gibson BW "The lbgAB gene cluster of Haemophilus ducreyi encodes a b-1,4-galactosyltransferase and an a-1,6-DD-heptosyltransferase involved in lipooligosaccharide biosynthesis" -
Infection and Immunity 70(6) (2002) 2853-2861
All Haemophilus ducreyi strains examined contain a lipooligosaccharide (LOS) consisting of a single but variable branch oligosaccharide that emanates off the first heptose (Hep-I) of a conserved Hep(3)-phosphorylated 3-deoxy-D-manno-octulosonic acid-lipid A core. In a previous report, identification of tandem genes, lbgA and lbgB, that are involved in LOS biosynthesis was described (Stevens et al., Infect. Immun. 65:651-660, 1997). In a separate study, the same gene cluster was identified and the lbgB (losB) gene was found to be required for transfer of the second sugar, D-glycero-D-manno-heptose (DD-Hep), of the major branch structure (Gibson et al., J. Bacteriol. 179:5062-5071, 1997). In this study, we identified the function of the neighboring upstream gene, lbgA, and found that it is necessary for addition of the third sugar in the dominant oligosaccharide branch, a galactose-linked β1→4, to the DD-Hep. LOS from an lbgA mutant and an lbgAB double mutant were isolated and were characterized by sodium dodecyl sulfate-polyacrylamide gel electrophoresis, carbohydrate analysis, mass spectrometry, and nuclear magnetic resonance spectroscopy. The results showed that the mutant strains synthesize truncated LOS glycoforms that terminate after addition of the first glucose (lbgAB) or the disaccharide DDHep α1→6 Glcβ1 (lbgA) that is attached to the heptose core. Both mutants show a significant reduction in the ability to adhere to human keratinocytes. Although minor differences were observed after two-dimensional gel electrophoresis of total proteins from the wild-type and mutant strains, the expression levels of the vast majority of proteins were unchanged, suggesting that the differences in adherence and invasion are due to differences in LOS. These studies add to the mounting evidence for a role of full-length LOS structures in the pathophysiology of H. ducreyi infection.
Haemophilus, lipopolysaccharides, Haemophilus ducreyi, Molecular Sequence Data, gene cluster, glycosyltransferases, Magnetic Resonance Spectroscopy, Bacterial Adhesion, Keratinocytes
NCBI PubMed ID: 12010972Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: bgibson@buckinstitute.org
Institutions: Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA, Children's Research Institute and The Ohio State University, Columbus, Ohio 43205-26962, Southwestern Medical Center, University of Texas, Dallas, Texas 75235-90483, State University of New York, Buffalo, New York 142144, and Buck Institute for Age Research, Novato, California 949455
Methods: NMR, MS, composition analysis, genetic methods, linkage analysis
- Article ID: 1175
Schilling B, Gibson BW, Filiatrault M, Campagnari AA "Characterization of lipooligosaccharides from Haemophilus ducreyi containing polylactosamine repeats" -
Journal of the American Society for Mass Spectrometry 13(6) (2002) 724-734
Haemophilus ducreyi, a gram-negative human mucosal pathogen, is one of the principal causes of genital ulcer disease. The lipooligosaccharides (LOS) of these bacteria are considered to be a major virulence factor and have been implicated in the adherence and invasion of H. ducreyi to several human cell types. An isogenic heptosyltransferase-III knockout strain (waaQ) was recently constructed from H. ducreyi 35000 wild-type strain and immunochemical and molecular weight data of the isolated LOS suggested the presence of poly-N-acetyllactosamine (LacNAc) (Filiatrault et al., Infect. Immun. 2000, 68, 3352-3361). In this present study, the structures of these novel LOS-glycoforms were characterized by matrix-assisted laser desorption/ionization (MALDI) and electrospray ionization (ESI) mass spectrometry in combination with exoglycosidase digestion. Detailed structural information was obtained for the oligosaccharide (OS) portions of these LOS showing between one to five linear LacNAc repeats on the non-reducing terminus of the main oligosaccharide branch. When grown on solid media, the organism produced LacNAc repeats that were further modified by the addition of sialic acid. Enzymatic digestion with β-galactosidase, β-N- acetylhexosaminidase, and neuraminidase type VI-A yielded truncated glycoforms consistent with a polyLacNAc structure capped at various end points with sialic acid. ESI-MS/MS mass spectrometry on a quadrupole time-of-flight instrument was particularly effective in obtaining detailed structural information on the least abundant, high-mass glycoforms. Although LOS containing terminal di-LacNAc have been reported, this is the first time to our knowledge that a linear polyLacNAc structure has been characterized in bacteria
Lipopolysaccharide, Haemophilus, lipopolysaccharides, oligosaccharide, structure, Haemophilus ducreyi, Lipooligosaccharide, blotting, chemistry, disease, human, LOS, strain, structural, Support, terminal, virulence, characterization, cell, molecular, Research, solid, adherence, acid, type, factor, wild type, bacteria, electrospray, hydrolysis, spectrometry, sugar, lactosamine, mass spectrometry, enzymatic, modified, ionization, sialic acid, MALDI, immunochemical, lipooligosaccharides, Gram-negative, pathogen, sugars, nonreducing, time, Western, amino, linear, culture, isogenic, virulence factor, U.S.Gov't, molecular weight, Matrix-Assisted Laser Desorption-Ionization, glycoside, amino sugar, terminus, United States, electrophoresis, Mass, Electrospray Ionization, medium, electrospray-ionization, P.H.S., LacNAc, amino sugars, Culture Media, desorption/ionization, Polyacrylamide Gel, genital, Glycoside Hydrolases, hydrolase, invasion, laser desorption/ionization, matrix-assisted, matrix-assisted laser, mucosal, neuraminidase, ulcer
NCBI PubMed ID: 12056572Journal NLM ID: 9010412Publisher: Elsevier
Correspondence: bgidson@Buckistitute.org
Institutions: Buck Institute for Age Research, Novato, California 94945, USA
Methods: NMR
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6. Compound ID: 283
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 75
Filiatrault MJ, Gibson BW, Schilling B, Sun SH, Munson RS, Campagnari AA "Construction and characterization of Haemophilus ducreyi lipooligosaccharide (LOS) mutants defective in expression of heptosyltransferase III and b1,4-glucosyltransferase: Identification of LOS glycoforms containing lactosamine repeats" -
Infection and Immunity 68(6) (2000) 3352-3361
To begin to understand the role of the lipooligosaccharide (LOS) molecule in chancroid infections, we constructed mutants defective in expression of glycosyltransferase genes. Pyocin lysis and immunoscreening was used to identify a LOS mutant of Haemophilus ducreyi 35000. This mutant, HD35000R, produced a LOS molecule that lacked the monoclonal antibody 3F11 epitope and migrated with an increased mobility on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). Structural studies indicated that the principal LOS glycoform contains lipid A, Kdo, and two of the three core heptose residues. HD35000R was transformed with a plasmid library of H. ducreyi 35000 DNA, and a clone producing the wild-type LOS was identified. Sequence analysis of the plasmid insert revealed one open reading frame (ORF) that encodes a protein with homology to the WaaQ (heptosyltransferase III) of Escherichia coli. A second ORF had homology to the LgtF (glucosyltransferase) of Neisseria meningitidis. Individual isogenic mutants lacking expression of the putative H. ducreyi heptosyltransferase III, the putative glucosyltransferase, and both glycosyltransferases were constructed and characterized. Each mutant was complemented with the representative wild-type genes in trans to restore expression of parental LOS and confirm the function of each enzyme. Matrix-assisted laser desorption ionization mass spectrometry and SDS-PAGE analysis identified several unique LOS glycoforms containing di-, tri-, and poly-N-acetyllactosamine repeats added to the terminal region of the main LOS branch synthesized by the heptosyltransferase III mutant. These novel H. ducreyi mutants provide important tools for studying the regulation of LOS assembly and biosynthesis
Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, expression, LOS, characterization, identification, mutant, mutants, construction, heptosyltransferase, lactosamine
NCBI PubMed ID: 10816485Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: AAC@acsu.buffalo.edu
Institutions: Department of Microbiology, Department of Medicine, Division of Infectious Diseases, and Center for Microbial Pathogenesis, University at Buffalo, Buffalo, New York 14214, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA3, and Children's Research Institute4 and Department of Molecular Virology, Immunology, and Medical Genetics,5 Ohio State University, Columbus, Ohio 43205-2696
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7. Compound ID: 284
L-gro-a-D-manHepp-(1-3)-+
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 75
Filiatrault MJ, Gibson BW, Schilling B, Sun SH, Munson RS, Campagnari AA "Construction and characterization of Haemophilus ducreyi lipooligosaccharide (LOS) mutants defective in expression of heptosyltransferase III and b1,4-glucosyltransferase: Identification of LOS glycoforms containing lactosamine repeats" -
Infection and Immunity 68(6) (2000) 3352-3361
To begin to understand the role of the lipooligosaccharide (LOS) molecule in chancroid infections, we constructed mutants defective in expression of glycosyltransferase genes. Pyocin lysis and immunoscreening was used to identify a LOS mutant of Haemophilus ducreyi 35000. This mutant, HD35000R, produced a LOS molecule that lacked the monoclonal antibody 3F11 epitope and migrated with an increased mobility on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). Structural studies indicated that the principal LOS glycoform contains lipid A, Kdo, and two of the three core heptose residues. HD35000R was transformed with a plasmid library of H. ducreyi 35000 DNA, and a clone producing the wild-type LOS was identified. Sequence analysis of the plasmid insert revealed one open reading frame (ORF) that encodes a protein with homology to the WaaQ (heptosyltransferase III) of Escherichia coli. A second ORF had homology to the LgtF (glucosyltransferase) of Neisseria meningitidis. Individual isogenic mutants lacking expression of the putative H. ducreyi heptosyltransferase III, the putative glucosyltransferase, and both glycosyltransferases were constructed and characterized. Each mutant was complemented with the representative wild-type genes in trans to restore expression of parental LOS and confirm the function of each enzyme. Matrix-assisted laser desorption ionization mass spectrometry and SDS-PAGE analysis identified several unique LOS glycoforms containing di-, tri-, and poly-N-acetyllactosamine repeats added to the terminal region of the main LOS branch synthesized by the heptosyltransferase III mutant. These novel H. ducreyi mutants provide important tools for studying the regulation of LOS assembly and biosynthesis
Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, expression, LOS, characterization, identification, mutant, mutants, construction, heptosyltransferase, lactosamine
NCBI PubMed ID: 10816485Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: AAC@acsu.buffalo.edu
Institutions: Department of Microbiology, Department of Medicine, Division of Infectious Diseases, and Center for Microbial Pathogenesis, University at Buffalo, Buffalo, New York 14214, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA3, and Children's Research Institute4 and Department of Molecular Virology, Immunology, and Medical Genetics,5 Ohio State University, Columbus, Ohio 43205-2696
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8. Compound ID: 285
L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 75
Filiatrault MJ, Gibson BW, Schilling B, Sun SH, Munson RS, Campagnari AA "Construction and characterization of Haemophilus ducreyi lipooligosaccharide (LOS) mutants defective in expression of heptosyltransferase III and b1,4-glucosyltransferase: Identification of LOS glycoforms containing lactosamine repeats" -
Infection and Immunity 68(6) (2000) 3352-3361
To begin to understand the role of the lipooligosaccharide (LOS) molecule in chancroid infections, we constructed mutants defective in expression of glycosyltransferase genes. Pyocin lysis and immunoscreening was used to identify a LOS mutant of Haemophilus ducreyi 35000. This mutant, HD35000R, produced a LOS molecule that lacked the monoclonal antibody 3F11 epitope and migrated with an increased mobility on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). Structural studies indicated that the principal LOS glycoform contains lipid A, Kdo, and two of the three core heptose residues. HD35000R was transformed with a plasmid library of H. ducreyi 35000 DNA, and a clone producing the wild-type LOS was identified. Sequence analysis of the plasmid insert revealed one open reading frame (ORF) that encodes a protein with homology to the WaaQ (heptosyltransferase III) of Escherichia coli. A second ORF had homology to the LgtF (glucosyltransferase) of Neisseria meningitidis. Individual isogenic mutants lacking expression of the putative H. ducreyi heptosyltransferase III, the putative glucosyltransferase, and both glycosyltransferases were constructed and characterized. Each mutant was complemented with the representative wild-type genes in trans to restore expression of parental LOS and confirm the function of each enzyme. Matrix-assisted laser desorption ionization mass spectrometry and SDS-PAGE analysis identified several unique LOS glycoforms containing di-, tri-, and poly-N-acetyllactosamine repeats added to the terminal region of the main LOS branch synthesized by the heptosyltransferase III mutant. These novel H. ducreyi mutants provide important tools for studying the regulation of LOS assembly and biosynthesis
Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, expression, LOS, characterization, identification, mutant, mutants, construction, heptosyltransferase, lactosamine
NCBI PubMed ID: 10816485Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: AAC@acsu.buffalo.edu
Institutions: Department of Microbiology, Department of Medicine, Division of Infectious Diseases, and Center for Microbial Pathogenesis, University at Buffalo, Buffalo, New York 14214, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA3, and Children's Research Institute4 and Department of Molecular Virology, Immunology, and Medical Genetics,5 Ohio State University, Columbus, Ohio 43205-2696
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9. Compound ID: 286
L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 75
Filiatrault MJ, Gibson BW, Schilling B, Sun SH, Munson RS, Campagnari AA "Construction and characterization of Haemophilus ducreyi lipooligosaccharide (LOS) mutants defective in expression of heptosyltransferase III and b1,4-glucosyltransferase: Identification of LOS glycoforms containing lactosamine repeats" -
Infection and Immunity 68(6) (2000) 3352-3361
To begin to understand the role of the lipooligosaccharide (LOS) molecule in chancroid infections, we constructed mutants defective in expression of glycosyltransferase genes. Pyocin lysis and immunoscreening was used to identify a LOS mutant of Haemophilus ducreyi 35000. This mutant, HD35000R, produced a LOS molecule that lacked the monoclonal antibody 3F11 epitope and migrated with an increased mobility on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). Structural studies indicated that the principal LOS glycoform contains lipid A, Kdo, and two of the three core heptose residues. HD35000R was transformed with a plasmid library of H. ducreyi 35000 DNA, and a clone producing the wild-type LOS was identified. Sequence analysis of the plasmid insert revealed one open reading frame (ORF) that encodes a protein with homology to the WaaQ (heptosyltransferase III) of Escherichia coli. A second ORF had homology to the LgtF (glucosyltransferase) of Neisseria meningitidis. Individual isogenic mutants lacking expression of the putative H. ducreyi heptosyltransferase III, the putative glucosyltransferase, and both glycosyltransferases were constructed and characterized. Each mutant was complemented with the representative wild-type genes in trans to restore expression of parental LOS and confirm the function of each enzyme. Matrix-assisted laser desorption ionization mass spectrometry and SDS-PAGE analysis identified several unique LOS glycoforms containing di-, tri-, and poly-N-acetyllactosamine repeats added to the terminal region of the main LOS branch synthesized by the heptosyltransferase III mutant. These novel H. ducreyi mutants provide important tools for studying the regulation of LOS assembly and biosynthesis
Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, expression, LOS, characterization, identification, mutant, mutants, construction, heptosyltransferase, lactosamine
NCBI PubMed ID: 10816485Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: AAC@acsu.buffalo.edu
Institutions: Department of Microbiology, Department of Medicine, Division of Infectious Diseases, and Center for Microbial Pathogenesis, University at Buffalo, Buffalo, New York 14214, Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA3, and Children's Research Institute4 and Department of Molecular Virology, Immunology, and Medical Genetics,5 Ohio State University, Columbus, Ohio 43205-2696
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10. Compound ID: 845
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 233
Filiatrault MJ, Munson RS, Campagnari AA "Genetic analysis of a pyocin-resistant lipooligosaccharide (LOS) mutant of Haemophilus ducreyi: Restoration of full-length LOS restores pyocin sensitivity" -
Journal of Bacteriology 183(19) (2001) 5756-5761
DNA sequence and Southern blot analyses were used to determine the genetic defect of a Haemophilus ducreyi pyocin-resistant lipooligosaccharide (LOS) mutant, HD35000R. The region of the HD35000R chromosome containing the suspected mutation was amplified, and sequence analysis detected a 3,189-bp deletion. This deletion resulted in the loss of the entire waaQ gene, another open reading frame that encodes a putative homolog to a hypothetical protein (HI0461) of H. influenzae, the gene encoding an argininosuccinate synthase homolog, and a change in the 3' sequence of the lgtF gene. Southern blot analysis confirmed that no genomic rearrangements had occurred. Isogenic LOS mutants and the respective complemented mutants were evaluated for susceptibility to pyocin C. The mutants expressing truncated LOS were resistant to lysis by pyocin C, and complementation restored sensitivity to the pyocin. We conclude that HD35000R is defective in both glycosyltransferase genes and that pyocin resistance is due to truncation of the full-length LOS molecule
genetic, Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, LOS, analysis, mutant, pyocin, sensitivity
NCBI PubMed ID: 11544241Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: aac@ascu.buffalo.edu
Institutions: Department of Microbiology, State University of New York at Buffalo, Buffalo, New York 14214, USA
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11. Compound ID: 848
L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 233
Filiatrault MJ, Munson RS, Campagnari AA "Genetic analysis of a pyocin-resistant lipooligosaccharide (LOS) mutant of Haemophilus ducreyi: Restoration of full-length LOS restores pyocin sensitivity" -
Journal of Bacteriology 183(19) (2001) 5756-5761
DNA sequence and Southern blot analyses were used to determine the genetic defect of a Haemophilus ducreyi pyocin-resistant lipooligosaccharide (LOS) mutant, HD35000R. The region of the HD35000R chromosome containing the suspected mutation was amplified, and sequence analysis detected a 3,189-bp deletion. This deletion resulted in the loss of the entire waaQ gene, another open reading frame that encodes a putative homolog to a hypothetical protein (HI0461) of H. influenzae, the gene encoding an argininosuccinate synthase homolog, and a change in the 3' sequence of the lgtF gene. Southern blot analysis confirmed that no genomic rearrangements had occurred. Isogenic LOS mutants and the respective complemented mutants were evaluated for susceptibility to pyocin C. The mutants expressing truncated LOS were resistant to lysis by pyocin C, and complementation restored sensitivity to the pyocin. We conclude that HD35000R is defective in both glycosyltransferase genes and that pyocin resistance is due to truncation of the full-length LOS molecule
genetic, Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, LOS, analysis, mutant, pyocin, sensitivity
NCBI PubMed ID: 11544241Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: aac@ascu.buffalo.edu
Institutions: Department of Microbiology, State University of New York at Buffalo, Buffalo, New York 14214, USA
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12. Compound ID: 849
L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 233
Filiatrault MJ, Munson RS, Campagnari AA "Genetic analysis of a pyocin-resistant lipooligosaccharide (LOS) mutant of Haemophilus ducreyi: Restoration of full-length LOS restores pyocin sensitivity" -
Journal of Bacteriology 183(19) (2001) 5756-5761
DNA sequence and Southern blot analyses were used to determine the genetic defect of a Haemophilus ducreyi pyocin-resistant lipooligosaccharide (LOS) mutant, HD35000R. The region of the HD35000R chromosome containing the suspected mutation was amplified, and sequence analysis detected a 3,189-bp deletion. This deletion resulted in the loss of the entire waaQ gene, another open reading frame that encodes a putative homolog to a hypothetical protein (HI0461) of H. influenzae, the gene encoding an argininosuccinate synthase homolog, and a change in the 3' sequence of the lgtF gene. Southern blot analysis confirmed that no genomic rearrangements had occurred. Isogenic LOS mutants and the respective complemented mutants were evaluated for susceptibility to pyocin C. The mutants expressing truncated LOS were resistant to lysis by pyocin C, and complementation restored sensitivity to the pyocin. We conclude that HD35000R is defective in both glycosyltransferase genes and that pyocin resistance is due to truncation of the full-length LOS molecule
genetic, Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, LOS, analysis, mutant, pyocin, sensitivity
NCBI PubMed ID: 11544241Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: aac@ascu.buffalo.edu
Institutions: Department of Microbiology, State University of New York at Buffalo, Buffalo, New York 14214, USA
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13. Compound ID: 850
L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 233
Filiatrault MJ, Munson RS, Campagnari AA "Genetic analysis of a pyocin-resistant lipooligosaccharide (LOS) mutant of Haemophilus ducreyi: Restoration of full-length LOS restores pyocin sensitivity" -
Journal of Bacteriology 183(19) (2001) 5756-5761
DNA sequence and Southern blot analyses were used to determine the genetic defect of a Haemophilus ducreyi pyocin-resistant lipooligosaccharide (LOS) mutant, HD35000R. The region of the HD35000R chromosome containing the suspected mutation was amplified, and sequence analysis detected a 3,189-bp deletion. This deletion resulted in the loss of the entire waaQ gene, another open reading frame that encodes a putative homolog to a hypothetical protein (HI0461) of H. influenzae, the gene encoding an argininosuccinate synthase homolog, and a change in the 3' sequence of the lgtF gene. Southern blot analysis confirmed that no genomic rearrangements had occurred. Isogenic LOS mutants and the respective complemented mutants were evaluated for susceptibility to pyocin C. The mutants expressing truncated LOS were resistant to lysis by pyocin C, and complementation restored sensitivity to the pyocin. We conclude that HD35000R is defective in both glycosyltransferase genes and that pyocin resistance is due to truncation of the full-length LOS molecule
genetic, Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, LOS, analysis, mutant, pyocin, sensitivity
NCBI PubMed ID: 11544241Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: aac@ascu.buffalo.edu
Institutions: Department of Microbiology, State University of New York at Buffalo, Buffalo, New York 14214, USA
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14. Compound ID: 851
L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130655,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_150939,IEDB_151531,IEDB_158550,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 233
Filiatrault MJ, Munson RS, Campagnari AA "Genetic analysis of a pyocin-resistant lipooligosaccharide (LOS) mutant of Haemophilus ducreyi: Restoration of full-length LOS restores pyocin sensitivity" -
Journal of Bacteriology 183(19) (2001) 5756-5761
DNA sequence and Southern blot analyses were used to determine the genetic defect of a Haemophilus ducreyi pyocin-resistant lipooligosaccharide (LOS) mutant, HD35000R. The region of the HD35000R chromosome containing the suspected mutation was amplified, and sequence analysis detected a 3,189-bp deletion. This deletion resulted in the loss of the entire waaQ gene, another open reading frame that encodes a putative homolog to a hypothetical protein (HI0461) of H. influenzae, the gene encoding an argininosuccinate synthase homolog, and a change in the 3' sequence of the lgtF gene. Southern blot analysis confirmed that no genomic rearrangements had occurred. Isogenic LOS mutants and the respective complemented mutants were evaluated for susceptibility to pyocin C. The mutants expressing truncated LOS were resistant to lysis by pyocin C, and complementation restored sensitivity to the pyocin. We conclude that HD35000R is defective in both glycosyltransferase genes and that pyocin resistance is due to truncation of the full-length LOS molecule
genetic, Haemophilus, Haemophilus ducreyi, Lipooligosaccharide, LOS, analysis, mutant, pyocin, sensitivity
NCBI PubMed ID: 11544241Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: aac@ascu.buffalo.edu
Institutions: Department of Microbiology, State University of New York at Buffalo, Buffalo, New York 14214, USA
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15. Compound ID: 911
a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-3)-+
|
b-D-Galp-(1-4)-+ |
| |
D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1--/lipid A/
|
L-gro-a-D-manHepp-(1-6)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
- Article ID: 2380
Michon F, Shaw DH, Banoub JH "Structure of the lipopolysaccharide core isolated from a human strain of Aeromonas hydrophila" -
European Journal of Biochemistry 145 (1984) 107-114
Lipopolysaccharide was isolated from the cell-walls of a human strain of Aeromonas hydrophila by the aqueous phenol method in 0.58% yield (based on dry weight of bacteria). The lipopolysaccharide consisted of SR-polysaccharide, core-oligosaccharide and lipid A; there was no O-specific polysaccharide. The core had the composition D-galactose, D-glucose, D-glycero-D-manno-heptose, L-glycero-D-manno-heptose and D-glucosamine in a molar ratio of 1:1:2:4:1. Glucosamine was linked to an L-glycero-D-manno-heptose residue by a bond which was resistant to hydrolysis. The D-glucosamine-(1→7)-LD-heptose disaccharide was isolated and identified by the mass spectrum of its methylated alditol and the heptose residue not observed under normal hydrolysis conditions was easily determined after deamination of the complete core. Methylation analysis, chemical degradation, periodate and chromium trioxide oxidations and nuclear magnetic resonance (13C and 1H NMR) spectroscopy were used to identify the structure of the core oligosaccharide as: (formula: see text)
NCBI PubMed ID: 6489347Publication DOI: 10.1111/j.1432-1033.1984.tb08528.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Fisheries Research Branch, Northwest‐Atlantic Fisheries Centre, P. O. Box 5667, St John's, Newfoundland, Canada
Methods: 13C NMR, 1H NMR, GC-MS
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