Found 365 structures.
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1. Compound ID: 88
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?%b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
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EtN-(1--P--6)--+ | P-4)-+
| | |
b-D-Galp-(1-2)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_148488,IEDB_190606,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: 18
Borrelli S, Hegedus O, Shaw DH, Jansson P, Lindberg AA "The tetrasaccharide L-a-D-heptose1->2-L-a-D-heptose1->3-L-a-D-heptose1->(3-deoxy-D-manno-octulosonic acid) and phosphate in lipid A define the conserved epitope in Haemophilus lipopolysaccharides recognized by a monoclonal antibody" -
Infection and Immunity 63 (1995) 3683-3692
A murine monoclonal antibody, MAHI 3 (immunoglobulin G2b), that is broadly reactive with Haemophilus influenzae lipopolysaccharides (LPSs) but nonreactive with all enterobacterial LPSs tested was generated by fusing mouse myeloma cells with spleen cells of BALB/c mice immunized with azide-killed H. influenzae RM.7004. MAHI 3 bound to all H. influenzae, all other human Haemophilus spp., all Bordetella pertussis and Bordetella parapertussis, and all Aeromonas spp. tested but not to any Neisseria or Moraxella catarrhalis strains, as determined by enzyme immunoassay, colony dot immunoblotting, and immunoblotting. In an inhibition enzyme immunoassay, MAHI 3 reacted with all 45 H. influenzae LPSs tested but not with the LPS from the rough mutant I69 Rd-/b+, which has only 3-deoxy-D-manno-octulosonic acid (P) [Kdop(P)] and lipid A. The antibody was not inhibited by H. influenzae lipid A or lipid-free polysaccharide isolated after mild acid hydrolysis. Only native LPSs show positive inhibitory activity, indicating that part of lipid A is involved in the binding of MAHI 3. From the results, it is indicated that the structural element recognized by MAHI 3 is Hep α1→2 Hep α1→3 Hep α1→ Kdo together with part of lipid A, including the phosphate
Lipopolysaccharide, Haemophilus, L-glycero-D-manno-heptose, lipopolysaccharides, LPS, core, tetrasaccharide, acid, Kdo, antibodies, antibody, conserved, epitope, lipid, lipid A, monoclonal, monoclonal antibodies, monoclonal antibody, phosphate, recognition
NCBI PubMed ID: 7543887Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: Pererk.Jansson@kfc.m13.hs.sll.se
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge, Sweden
Methods: de-O-acylation, SDS-PAGE, alkaline de-O-N-acylation, dephosphorylation, chemical analysis, EIA, inhibition studies, dot immunoblotting
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2. Compound ID: 89
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b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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EtN-(1--P--6)--+ | P-4)-+
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EtN-(1--P--6)--L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 18
Borrelli S, Hegedus O, Shaw DH, Jansson P, Lindberg AA "The tetrasaccharide L-a-D-heptose1->2-L-a-D-heptose1->3-L-a-D-heptose1->(3-deoxy-D-manno-octulosonic acid) and phosphate in lipid A define the conserved epitope in Haemophilus lipopolysaccharides recognized by a monoclonal antibody" -
Infection and Immunity 63 (1995) 3683-3692
A murine monoclonal antibody, MAHI 3 (immunoglobulin G2b), that is broadly reactive with Haemophilus influenzae lipopolysaccharides (LPSs) but nonreactive with all enterobacterial LPSs tested was generated by fusing mouse myeloma cells with spleen cells of BALB/c mice immunized with azide-killed H. influenzae RM.7004. MAHI 3 bound to all H. influenzae, all other human Haemophilus spp., all Bordetella pertussis and Bordetella parapertussis, and all Aeromonas spp. tested but not to any Neisseria or Moraxella catarrhalis strains, as determined by enzyme immunoassay, colony dot immunoblotting, and immunoblotting. In an inhibition enzyme immunoassay, MAHI 3 reacted with all 45 H. influenzae LPSs tested but not with the LPS from the rough mutant I69 Rd-/b+, which has only 3-deoxy-D-manno-octulosonic acid (P) [Kdop(P)] and lipid A. The antibody was not inhibited by H. influenzae lipid A or lipid-free polysaccharide isolated after mild acid hydrolysis. Only native LPSs show positive inhibitory activity, indicating that part of lipid A is involved in the binding of MAHI 3. From the results, it is indicated that the structural element recognized by MAHI 3 is Hep α1→2 Hep α1→3 Hep α1→ Kdo together with part of lipid A, including the phosphate
Lipopolysaccharide, Haemophilus, L-glycero-D-manno-heptose, lipopolysaccharides, LPS, core, tetrasaccharide, acid, Kdo, antibodies, antibody, conserved, epitope, lipid, lipid A, monoclonal, monoclonal antibodies, monoclonal antibody, phosphate, recognition
NCBI PubMed ID: 7543887Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: Pererk.Jansson@kfc.m13.hs.sll.se
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge, Sweden
Methods: de-O-acylation, SDS-PAGE, alkaline de-O-N-acylation, dephosphorylation, chemical analysis, EIA, inhibition studies, dot immunoblotting
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3. Compound ID: 90
|
b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+ P-4)-+
| |
L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 18
Borrelli S, Hegedus O, Shaw DH, Jansson P, Lindberg AA "The tetrasaccharide L-a-D-heptose1->2-L-a-D-heptose1->3-L-a-D-heptose1->(3-deoxy-D-manno-octulosonic acid) and phosphate in lipid A define the conserved epitope in Haemophilus lipopolysaccharides recognized by a monoclonal antibody" -
Infection and Immunity 63 (1995) 3683-3692
A murine monoclonal antibody, MAHI 3 (immunoglobulin G2b), that is broadly reactive with Haemophilus influenzae lipopolysaccharides (LPSs) but nonreactive with all enterobacterial LPSs tested was generated by fusing mouse myeloma cells with spleen cells of BALB/c mice immunized with azide-killed H. influenzae RM.7004. MAHI 3 bound to all H. influenzae, all other human Haemophilus spp., all Bordetella pertussis and Bordetella parapertussis, and all Aeromonas spp. tested but not to any Neisseria or Moraxella catarrhalis strains, as determined by enzyme immunoassay, colony dot immunoblotting, and immunoblotting. In an inhibition enzyme immunoassay, MAHI 3 reacted with all 45 H. influenzae LPSs tested but not with the LPS from the rough mutant I69 Rd-/b+, which has only 3-deoxy-D-manno-octulosonic acid (P) [Kdop(P)] and lipid A. The antibody was not inhibited by H. influenzae lipid A or lipid-free polysaccharide isolated after mild acid hydrolysis. Only native LPSs show positive inhibitory activity, indicating that part of lipid A is involved in the binding of MAHI 3. From the results, it is indicated that the structural element recognized by MAHI 3 is Hep α1→2 Hep α1→3 Hep α1→ Kdo together with part of lipid A, including the phosphate
Lipopolysaccharide, Haemophilus, L-glycero-D-manno-heptose, lipopolysaccharides, LPS, core, tetrasaccharide, acid, Kdo, antibodies, antibody, conserved, epitope, lipid, lipid A, monoclonal, monoclonal antibodies, monoclonal antibody, phosphate, recognition
NCBI PubMed ID: 7543887Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: Pererk.Jansson@kfc.m13.hs.sll.se
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge, Sweden
Methods: de-O-acylation, SDS-PAGE, alkaline de-O-N-acylation, dephosphorylation, chemical analysis, EIA, inhibition studies, dot immunoblotting
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4. Compound ID: 91
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-4)-+
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-D-gro-b-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 18
Borrelli S, Hegedus O, Shaw DH, Jansson P, Lindberg AA "The tetrasaccharide L-a-D-heptose1->2-L-a-D-heptose1->3-L-a-D-heptose1->(3-deoxy-D-manno-octulosonic acid) and phosphate in lipid A define the conserved epitope in Haemophilus lipopolysaccharides recognized by a monoclonal antibody" -
Infection and Immunity 63 (1995) 3683-3692
A murine monoclonal antibody, MAHI 3 (immunoglobulin G2b), that is broadly reactive with Haemophilus influenzae lipopolysaccharides (LPSs) but nonreactive with all enterobacterial LPSs tested was generated by fusing mouse myeloma cells with spleen cells of BALB/c mice immunized with azide-killed H. influenzae RM.7004. MAHI 3 bound to all H. influenzae, all other human Haemophilus spp., all Bordetella pertussis and Bordetella parapertussis, and all Aeromonas spp. tested but not to any Neisseria or Moraxella catarrhalis strains, as determined by enzyme immunoassay, colony dot immunoblotting, and immunoblotting. In an inhibition enzyme immunoassay, MAHI 3 reacted with all 45 H. influenzae LPSs tested but not with the LPS from the rough mutant I69 Rd-/b+, which has only 3-deoxy-D-manno-octulosonic acid (P) [Kdop(P)] and lipid A. The antibody was not inhibited by H. influenzae lipid A or lipid-free polysaccharide isolated after mild acid hydrolysis. Only native LPSs show positive inhibitory activity, indicating that part of lipid A is involved in the binding of MAHI 3. From the results, it is indicated that the structural element recognized by MAHI 3 is Hep α1→2 Hep α1→3 Hep α1→ Kdo together with part of lipid A, including the phosphate
Lipopolysaccharide, Haemophilus, L-glycero-D-manno-heptose, lipopolysaccharides, LPS, core, tetrasaccharide, acid, Kdo, antibodies, antibody, conserved, epitope, lipid, lipid A, monoclonal, monoclonal antibodies, monoclonal antibody, phosphate, recognition
NCBI PubMed ID: 7543887Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: Pererk.Jansson@kfc.m13.hs.sll.se
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge, Sweden
Methods: de-O-acylation, SDS-PAGE, alkaline de-O-N-acylation, dephosphorylation, chemical analysis, EIA, inhibition studies, dot immunoblotting
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5. Compound ID: 126
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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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6. Compound ID: 154
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b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 33
Cancilla MT, Gaucher SP, Desaire H, Leary JA "Combined partial acid hydrolysis and electrospray ionization-mass spectrometry for the structural determination of oligosaccharides" -
Analytical Chemistry 72(13) (2000) 2901-2907
A general oligosaccharide acid hydrolysis method, amenable to electrospray ionization mass spectrometry (ESI-MS), is described that allows for hydrolysis of glycosidic bonds for both hexose- and N-acetylhexosamine-containing oligosaccharides. The partial acid hydrolysis of oligosaccharides is obtained by using an acid-exchange resin as the acid catalyst. A ladder sequence of the glycan is produced in solution that is directly analyzed by ESI tandem mass spectrometry, employing both ion trap and Fourier transform ion cyclotron resonance mass spectrometers, to provide sequence and linkage information. Unlike traditional acid hydrolysis procedures, there is minimal degradation of monosaccharide residues or deacetylation of N-acetylhexosamines by employing this technique. It is further demonstrated that the stereochemistry of the released monosaccharides and the anomeric configuration within disaccharides is determined by direct derivatization of the hydrolysate with Zn(dien)-Cl2 followed by ESI-MS/MS
oligosaccharide, structural, determination, structural determination, acid, Oligosaccharides, electrospray, hydrolysis, ionization mass spectrometry, spectrometry
NCBI PubMed ID: 10905325Journal NLM ID: 0370536Correspondence: leary@socrates.berkeley.edu
Institutions: College of Chemistry, University of California, Berkeley 94720-1460, USA
Methods: partial acid hydrolysis, ESI-MS, ESI-FTICR-MS, ESI-MS/MS
- Article ID: 1767
Phillips NJ, Apicella MA, Griffiss JML, Gibson BW "Structural characterization of the cell surface lipooligosaccharides from a nontypable strain of Haemophilus influenzae" -
Biochemistry 31 (1992) 4515-4526
Oligosaccharides released from the lipooligosaccharides (LOS) of Haemophilus influenzae nontypable strain 2019 by mild acid hydrolysis were fractionated by size exclusion chromatography and analyzed by liquid secondary ion mass spectrometry. The major component of the heterogeneous mixture was found to be a hexasaccharide of Mr 1366, which lost two phosphoethanolamine groups upon treatment with 48% aqueous HF. The dephosphorylated hexasaccharide was purified and shown by tandem mass spectrometry, composition analysis, methylation analysis, and two-dimensional nuclear magnetic resonance studies to be Gal β1→4 Glc β1→(Hep α1→2 Hep α1→3) 4Hep α1→5 anhydro-KDO, where Hep is L-glycero-D-manno-heptose and KDO is 3-deoxy-D-manno-octulosonic acid. An analogous structure containing authentic KDO was generated from LOS that had been HF-treated prior to acetic acid hydrolysis, suggesting that the reducing terminal anhydro-KDO moiety is produced as an artifact of the hydrolysis procedure by beta-elimination of a phosphate substituent from C-4 of KDO. Mass spectral analyses of O-deacylated LOS and free lipid A confirmed that, in addition to the two phosphoethanolamines on the oligosaccharide and two phosphates on the lipid A, another phosphate group exists on the KDO. This KDO does not appear to be further substituted with additional KDO residues in intact H. influenzae 2019 LOS. The terminal disaccharide epitope, Gal β1→4 Glc β1→, of the hexasaccharide is also present on lactosylceramide, a precursor to human blood group antigens. It is postulated that the presence of this structure on H. influenzae LOS may represent a form of host mimicry by the pathogen.
NCBI PubMed ID: 1581306Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA
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7. Compound ID: 171
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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/
|
a-D-Glcp-(1-6)-+ |
Show graphically |
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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8. Compound ID: 282
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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/ |
Show graphically |
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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9. Compound ID: 283
|
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)-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_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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10. Compound ID: 721
|
L-gro-a-D-manHepp-(1-6)-+ b-D-Glcp-(1-4)-+
| |
a-D-GlcpNAc-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-D-GlcNAc-ol
|
a-D-Glcp-(1-6)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 192
Vinogradov EV, Bock K, Holst O, Brade H "The structure of the lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)" -
European Journal of Biochemistry 233 (1995) 152-158
The lipopolysaccharides (LPS) from Vibrio cholerae 95R, a rough mutant strain of O1 V. cholerae 162 (Ogawa), and from smooth O1 V. cholerae 569B (Inaba) were de-O-acylated. In each case, one part of the products was treated with 48% aqueous HF which removed the phosphoryl and fructose residues, then reduced, de-N-acylated, and N-acetylated. Another part was de-N-acylated by treatment with hot KOH. The products of both degradation pathways were separated by high-performance anion-exchange chromatography. The major dephosphorylated and defructosylated product 1 was obtained in pure form, whereas the minor products 2 and 3 were eluted as a mixture, as were, from the second degradation, the phosphorylated oligosaccharides 4 (major product) and 5 (minor product). No phosphorylated component corresponding to oligosaccharide 3 could be identified by NMR spectroscopy in the latter mixture. The following structures of oligosaccharides 1-5 were established on the basis of monosaccharide and methylation analyses, Smith degradation, and 1H- and 13C NMR investigations (correlated, total correlated, NOE and heteronuclear correlation spectroscopy; all sugars are present as α-D-pyranoses except where indicated otherwise; Hep, L-glycero-D-manno-heptose; Kdo, 3-deoxy-D-manno-2-octulosonic acid). [formula: see text] In the untreated lipopolysaccharide, the amino group of the non-reducing terminal glucosamine residue is not substituted.
Lipopolysaccharide, Vibrio cholerae O1, core-lipid A structure
NCBI PubMed ID: 7588739Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Biochemische Mikrobiologis, Forschungsinstitut Borstel, Institut fur Experimentelle Biologie und Medizin, Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, Valby, Denmark
Methods: NMR-2D, NMR, HF solvolysis, dephosphorylation, chemical analysis, mild acid hydrolysis, alkaline degradation, HPAEC, defructosylation
- Article ID: 853
Knirel YA, Widmalm G, Senchenkova SN, Jansson P, Weintraub A "Structural studies on the short-chain lipopolysaccharide of Vibrio cholerae O139 Bengal" -
European Journal of Biochemistry 247 (1997) 402-410
A Vibrio cholerae O139 strain, MO10-T4, lacking capsular polysaccharide, produces a short-chain lipopolysaccharide (LPS), similar to enterobacterial SR strains. It was studied by acidic and alkaline degradation, dephosphorylation, sugar and methylation analysis, high-performance anion-exchange chromatography, one- and two-dimensional 1H-, 13C-, and 31P-NMR spectroscopy, and electrospray ionization mass spectrometry. The following structure was proposed for the core region of the LPS: [structure: see text] where PEtn stands for 2-aminoethyl phosphate, Fru for fructose, Hep for L-glycero-D-manno-heptose, and Kdo for 3-deoxy-D-manno-octulosonic acid; unless otherwise stated, the monosaccharide residues are D and present in the pyranose form. An O-acetyl group is present on a secondary position, tentatively O4 of the α-linked glucosyl group. Some LPS species contain an additional putative fructose residue whose location remains unknown. An O139-negative mutant strain, Bengal-2R, derived from V. cholerae O139, has also been investigated and shown to produce an O-antigen-lacking LPS similar to those from enterobacterial R strains, some of the LPS species containing the same core region as the strain MO10-T4 LPS and the other lacking the lateral heptose residue. The carbohydrate backbone core structure is the same for the V. cholerae O139 and V. cholerae O1 LPS, thus confirming the close relation between these bacteria; however, the 2-aminoethyl phosphate, the O-acetyl group, and the second fructose residue have not been reported for the O1 LPS. In the V. cholerae O139 strain MO10-T4 LPS, a short O-side chain is attached at position 3 of the 7-substituted heptose residue and has the same structure as one repeating unit of the V. cholerae O139 capsular polysaccharide. Some details of the structure proposed are at variance with those recently published for another V. cholerae O139 strain [Cox, A. D., Brisson, J.-R., Varma, V. & Perry, M. B. (1996) Carbohydr. Res. 290, 43-58; Cox, A. D. & Perry, M. B. (1996) Carbohydr. Res. 290, 59-65.]
Lipopolysaccharide, LPS, structure, structural, O-antigen, Kdo, phosphate, O-specific, cyclic, structural studies, ethanolamine, Vibrio, core-lipid A backbone, Vibrio cholerae, fructose, SR-type LPS, Vibrio cholerae O139, cross-reactive, colitose, O-acetyl, mutant strain
NCBI PubMed ID: 9249053Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pjansson@kfc.ki.se
Institutions: Clinical Research Centre, Huddinge Hospital, Huddinge, Sweden
Methods: NMR, ESI-MS, alkaline degradation, HPAEC, acid degradation
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11. Compound ID: 722
|
b-D-Glcp-(1-4)-+
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a-D-GlcpNAc-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-D-GlcNAc-ol
|
a-D-Glcp-(1-6)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 192
Vinogradov EV, Bock K, Holst O, Brade H "The structure of the lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)" -
European Journal of Biochemistry 233 (1995) 152-158
The lipopolysaccharides (LPS) from Vibrio cholerae 95R, a rough mutant strain of O1 V. cholerae 162 (Ogawa), and from smooth O1 V. cholerae 569B (Inaba) were de-O-acylated. In each case, one part of the products was treated with 48% aqueous HF which removed the phosphoryl and fructose residues, then reduced, de-N-acylated, and N-acetylated. Another part was de-N-acylated by treatment with hot KOH. The products of both degradation pathways were separated by high-performance anion-exchange chromatography. The major dephosphorylated and defructosylated product 1 was obtained in pure form, whereas the minor products 2 and 3 were eluted as a mixture, as were, from the second degradation, the phosphorylated oligosaccharides 4 (major product) and 5 (minor product). No phosphorylated component corresponding to oligosaccharide 3 could be identified by NMR spectroscopy in the latter mixture. The following structures of oligosaccharides 1-5 were established on the basis of monosaccharide and methylation analyses, Smith degradation, and 1H- and 13C NMR investigations (correlated, total correlated, NOE and heteronuclear correlation spectroscopy; all sugars are present as α-D-pyranoses except where indicated otherwise; Hep, L-glycero-D-manno-heptose; Kdo, 3-deoxy-D-manno-2-octulosonic acid). [formula: see text] In the untreated lipopolysaccharide, the amino group of the non-reducing terminal glucosamine residue is not substituted.
Lipopolysaccharide, Vibrio cholerae O1, core-lipid A structure
NCBI PubMed ID: 7588739Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Biochemische Mikrobiologis, Forschungsinstitut Borstel, Institut fur Experimentelle Biologie und Medizin, Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, Valby, Denmark
Methods: NMR-2D, NMR, HF solvolysis, dephosphorylation, chemical analysis, mild acid hydrolysis, alkaline degradation, HPAEC, defructosylation
- Article ID: 853
Knirel YA, Widmalm G, Senchenkova SN, Jansson P, Weintraub A "Structural studies on the short-chain lipopolysaccharide of Vibrio cholerae O139 Bengal" -
European Journal of Biochemistry 247 (1997) 402-410
A Vibrio cholerae O139 strain, MO10-T4, lacking capsular polysaccharide, produces a short-chain lipopolysaccharide (LPS), similar to enterobacterial SR strains. It was studied by acidic and alkaline degradation, dephosphorylation, sugar and methylation analysis, high-performance anion-exchange chromatography, one- and two-dimensional 1H-, 13C-, and 31P-NMR spectroscopy, and electrospray ionization mass spectrometry. The following structure was proposed for the core region of the LPS: [structure: see text] where PEtn stands for 2-aminoethyl phosphate, Fru for fructose, Hep for L-glycero-D-manno-heptose, and Kdo for 3-deoxy-D-manno-octulosonic acid; unless otherwise stated, the monosaccharide residues are D and present in the pyranose form. An O-acetyl group is present on a secondary position, tentatively O4 of the α-linked glucosyl group. Some LPS species contain an additional putative fructose residue whose location remains unknown. An O139-negative mutant strain, Bengal-2R, derived from V. cholerae O139, has also been investigated and shown to produce an O-antigen-lacking LPS similar to those from enterobacterial R strains, some of the LPS species containing the same core region as the strain MO10-T4 LPS and the other lacking the lateral heptose residue. The carbohydrate backbone core structure is the same for the V. cholerae O139 and V. cholerae O1 LPS, thus confirming the close relation between these bacteria; however, the 2-aminoethyl phosphate, the O-acetyl group, and the second fructose residue have not been reported for the O1 LPS. In the V. cholerae O139 strain MO10-T4 LPS, a short O-side chain is attached at position 3 of the 7-substituted heptose residue and has the same structure as one repeating unit of the V. cholerae O139 capsular polysaccharide. Some details of the structure proposed are at variance with those recently published for another V. cholerae O139 strain [Cox, A. D., Brisson, J.-R., Varma, V. & Perry, M. B. (1996) Carbohydr. Res. 290, 43-58; Cox, A. D. & Perry, M. B. (1996) Carbohydr. Res. 290, 59-65.]
Lipopolysaccharide, LPS, structure, structural, O-antigen, Kdo, phosphate, O-specific, cyclic, structural studies, ethanolamine, Vibrio, core-lipid A backbone, Vibrio cholerae, fructose, SR-type LPS, Vibrio cholerae O139, cross-reactive, colitose, O-acetyl, mutant strain
NCBI PubMed ID: 9249053Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pjansson@kfc.ki.se
Institutions: Clinical Research Centre, Huddinge Hospital, Huddinge, Sweden
Methods: NMR, ESI-MS, alkaline degradation, HPAEC, acid degradation
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12. Compound ID: 723
|
L-gro-a-D-manHepp-(1-6)-+ b-D-Glcp-(1-4)-+
| |
a-D-GlcpNAc-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpNAc-(1-6)-D-GlcNAc-ol |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_137340,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 192
Vinogradov EV, Bock K, Holst O, Brade H "The structure of the lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)" -
European Journal of Biochemistry 233 (1995) 152-158
The lipopolysaccharides (LPS) from Vibrio cholerae 95R, a rough mutant strain of O1 V. cholerae 162 (Ogawa), and from smooth O1 V. cholerae 569B (Inaba) were de-O-acylated. In each case, one part of the products was treated with 48% aqueous HF which removed the phosphoryl and fructose residues, then reduced, de-N-acylated, and N-acetylated. Another part was de-N-acylated by treatment with hot KOH. The products of both degradation pathways were separated by high-performance anion-exchange chromatography. The major dephosphorylated and defructosylated product 1 was obtained in pure form, whereas the minor products 2 and 3 were eluted as a mixture, as were, from the second degradation, the phosphorylated oligosaccharides 4 (major product) and 5 (minor product). No phosphorylated component corresponding to oligosaccharide 3 could be identified by NMR spectroscopy in the latter mixture. The following structures of oligosaccharides 1-5 were established on the basis of monosaccharide and methylation analyses, Smith degradation, and 1H- and 13C NMR investigations (correlated, total correlated, NOE and heteronuclear correlation spectroscopy; all sugars are present as α-D-pyranoses except where indicated otherwise; Hep, L-glycero-D-manno-heptose; Kdo, 3-deoxy-D-manno-2-octulosonic acid). [formula: see text] In the untreated lipopolysaccharide, the amino group of the non-reducing terminal glucosamine residue is not substituted.
Lipopolysaccharide, Vibrio cholerae O1, core-lipid A structure
NCBI PubMed ID: 7588739Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Biochemische Mikrobiologis, Forschungsinstitut Borstel, Institut fur Experimentelle Biologie und Medizin, Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, Valby, Denmark
Methods: NMR-2D, NMR, HF solvolysis, dephosphorylation, chemical analysis, mild acid hydrolysis, alkaline degradation, HPAEC, defructosylation
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13. Compound ID: 724
|
b-D-Fruf-(2-6)-b-D-Glcp-(1-4)-+
|
L-gro-a-D-manHepp-(1-6)-+ | P-4)-+ P-4)-+
| | | |
a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
a-D-Glcp-(1-6)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_137340,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 192
Vinogradov EV, Bock K, Holst O, Brade H "The structure of the lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)" -
European Journal of Biochemistry 233 (1995) 152-158
The lipopolysaccharides (LPS) from Vibrio cholerae 95R, a rough mutant strain of O1 V. cholerae 162 (Ogawa), and from smooth O1 V. cholerae 569B (Inaba) were de-O-acylated. In each case, one part of the products was treated with 48% aqueous HF which removed the phosphoryl and fructose residues, then reduced, de-N-acylated, and N-acetylated. Another part was de-N-acylated by treatment with hot KOH. The products of both degradation pathways were separated by high-performance anion-exchange chromatography. The major dephosphorylated and defructosylated product 1 was obtained in pure form, whereas the minor products 2 and 3 were eluted as a mixture, as were, from the second degradation, the phosphorylated oligosaccharides 4 (major product) and 5 (minor product). No phosphorylated component corresponding to oligosaccharide 3 could be identified by NMR spectroscopy in the latter mixture. The following structures of oligosaccharides 1-5 were established on the basis of monosaccharide and methylation analyses, Smith degradation, and 1H- and 13C NMR investigations (correlated, total correlated, NOE and heteronuclear correlation spectroscopy; all sugars are present as α-D-pyranoses except where indicated otherwise; Hep, L-glycero-D-manno-heptose; Kdo, 3-deoxy-D-manno-2-octulosonic acid). [formula: see text] In the untreated lipopolysaccharide, the amino group of the non-reducing terminal glucosamine residue is not substituted.
Lipopolysaccharide, Vibrio cholerae O1, core-lipid A structure
NCBI PubMed ID: 7588739Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Biochemische Mikrobiologis, Forschungsinstitut Borstel, Institut fur Experimentelle Biologie und Medizin, Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, Valby, Denmark
Methods: NMR-2D, NMR, HF solvolysis, dephosphorylation, chemical analysis, mild acid hydrolysis, alkaline degradation, HPAEC, defructosylation
- Article ID: 1451
Chatterjee SN, Chaudhuri K "Lipopolysaccharides of Vibrio cholerae. I. Physical and chemical characterization" -
Biochimica et Biophysica Acta 1639(2) (2003) 65-79
Vibrio cholerae is the causative organism of the disease cholera. The lipopolysaccharide (LPS) of V. cholerae plays an important role in eliciting the antibacterial immune response of the host and in classifying the vibrios into some 200 or more serogroups. This review presents an account of our up-to-date knowledge of the physical and chemical characteristics of the three constituents, lipid-A, core-polysaccharide (core-PS) and O-antigen polysaccharide (O-PS), of the LPS of V. cholerae of different serogroups including the disease-causing ones, O1 and O139. The structure and occurrence of the capsular polysaccharide (CPS) on V. cholerae O139 have been discussed as a relevant topic. Similarity and dissimilarity between the structures of LPS of different serogroups, and particularly between O22 and O139, have been analysed with a view to learning their role in the causation of the epidemic form of the disease by avoiding the host defence mechanism and in the evolution of the newer pathogenic strains in future. An idea of the emerging trends of research involving the use of immunogens prepared from synthetic oligosaccharides that mimic terminal epitopes of the O-PS of V. cholerae O1 in the development of a conjugate anti cholera vaccine is also discussed.
Lipopolysaccharide, structure, capsular polysaccharide, lipid A, serogroup, Vibrio cholerae
NCBI PubMed ID: 14559113Publication DOI: 10.1016/j.bbadis.2003.08.004Journal NLM ID: 0217513Publisher: Elsevier
Correspondence: sncac@sify.com (S.N. Chatterjee)
Institutions: Saha Institute of Nuclear Physics, 1/AF Bidhannagar, Sector-1, Calcutta-700 064, India, Biophysics Division, Indian Institute of Chemical Biology, Jadavpur, Calcutta-700 032, India
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14. Compound ID: 725
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b-D-Fruf-(2-6)-b-D-Glcp-(1-4)-+ P-4)-+ P-4)-+
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a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-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: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_137340,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 192
Vinogradov EV, Bock K, Holst O, Brade H "The structure of the lipid A-core region of the lipopolysaccharides from Vibrio cholerae O1 smooth strain 569B (Inaba) and rough mutant strain 95R (Ogawa)" -
European Journal of Biochemistry 233 (1995) 152-158
The lipopolysaccharides (LPS) from Vibrio cholerae 95R, a rough mutant strain of O1 V. cholerae 162 (Ogawa), and from smooth O1 V. cholerae 569B (Inaba) were de-O-acylated. In each case, one part of the products was treated with 48% aqueous HF which removed the phosphoryl and fructose residues, then reduced, de-N-acylated, and N-acetylated. Another part was de-N-acylated by treatment with hot KOH. The products of both degradation pathways were separated by high-performance anion-exchange chromatography. The major dephosphorylated and defructosylated product 1 was obtained in pure form, whereas the minor products 2 and 3 were eluted as a mixture, as were, from the second degradation, the phosphorylated oligosaccharides 4 (major product) and 5 (minor product). No phosphorylated component corresponding to oligosaccharide 3 could be identified by NMR spectroscopy in the latter mixture. The following structures of oligosaccharides 1-5 were established on the basis of monosaccharide and methylation analyses, Smith degradation, and 1H- and 13C NMR investigations (correlated, total correlated, NOE and heteronuclear correlation spectroscopy; all sugars are present as α-D-pyranoses except where indicated otherwise; Hep, L-glycero-D-manno-heptose; Kdo, 3-deoxy-D-manno-2-octulosonic acid). [formula: see text] In the untreated lipopolysaccharide, the amino group of the non-reducing terminal glucosamine residue is not substituted.
Lipopolysaccharide, Vibrio cholerae O1, core-lipid A structure
NCBI PubMed ID: 7588739Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Biochemische Mikrobiologis, Forschungsinstitut Borstel, Institut fur Experimentelle Biologie und Medizin, Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, Valby, Denmark
Methods: NMR-2D, NMR, HF solvolysis, dephosphorylation, chemical analysis, mild acid hydrolysis, alkaline degradation, HPAEC, defructosylation
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15. Compound ID: 845
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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)-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_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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Next 15 structure(s)
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