Found 195 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
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1. Compound ID: 108
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a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-+
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a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1--/Glcp(1-1)ceramide (ganglioside GQ1b) or the inner core-lipid A (lipopolysaccharide)/ |
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Structure type: oligomer
Aglycon: Glcp(1-1)ceramide (ganglioside GQ1b) or the inner core-lipid A (lipopolysaccharide)
Trivial name: ganglioside GQ1b
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_35,SB_39,SB_42,SB_68,SB_7,SB_70,SB_8,SB_84,SB_88,SB_96,SB_97
The structure is contained in the following publication(s):
- Article ID: 21
Bowes T, Wagner ER, Boffey J, Nicholl D, Cochrane L, Benboubetra M, Conner J, Furukawa K, Willison HJ "Tolerance to self gangliosides is the major factor restricting the antibody response to lipopolysaccharide core oligosaccharides in Campylobacter jejuni strains associated with Guillain-Barre syndrome" -
Infection and Immunity 70(9) (2002) 5008-5018
Guillain-Barre syndrome following Campylobacter jejuni infection is frequently associated with anti-ganglioside autoantibodies mediated by molecular mimicry with ganglioside-like oligosaccharides on bacterial lipopolysaccharide (LPS). The regulation of antibody responses to these T-cell-independent antigens is poorly understood, and only a minority of Campylobacter-infected individuals develop anti-ganglioside antibodies. This study investigates the response to gangliosides and LPS in strains of mice by using a range of immunization strategies. In normal mice following intraperitoneal immunization, antibody responses to gangliosides and LPS are low level but can be enhanced by the antigen format or coadministration of protein to recruit T-cell help. Class switching from the predominant immunoglobulin M (IgM) response to IgG3 occurs at low levels, suggesting B1-cell involvement. Systemic immunization results in poor responses. In GalNAc transferase knockout mice that lack all complex gangliosides and instead express high levels of GM3 and GD3, generation of anti-ganglioside antibodies upon immunization with either complex gangliosides or ganglioside-mimicking LPS is greatly enhanced and exhibits class switching to T-cell- dependent IgG isotypes and immunological memory, indicating that tolerance to self gangliosides is a major regulatory factor. Responses to GD3 are suppressed in knockout mice compared with wild-type mice, in which responses to GD3 are induced specifically by GD3 and as a result of polyclonal B-cell activation by LPS. The anti-ganglioside response generated in response to LPS is also dependent on the epitope density of the ganglioside mimicked and can be further manipulated by providing secondary signals via lipid A and CD40 ligation
Lipopolysaccharide, biosynthesis, antigen, lipopolysaccharides, LPS, oligosaccharide, core, chemistry, Bacterial, genetics, human, metabolism, pathogenicity, strain, molecular, transferase, antibodies, antibody, epitope, lipid, lipid A, Oligosaccharides, activation, animal, anti-ganglioside, antibody response, antigens, CD40, Autoantibodies, autoantibody, B cell, B-cell, Campylobacter, Campylobacter Infections, Campylobacter jejuni, Carbohydrate Sequence, class, complex, complications, core oligosaccharide, deficiency, density, enhanced, etiology, factor, Female, ganglioside, gangliosides, generation, Guillain-Barre syndrome, high, IgG, IgM, immunization, immunoglobulin, Immunoglobulin M, immunological, immunological memory, immunology, induced, infection, involvement, level, lipopolysaccharide core, lipopolysaccharide core oligosaccharide, liposomes, memory, mice, Inbred BALB C, Inbred C3H, Knockout, mimicry, molecular mimicry, Molecular Sequence Data, N-Acetylgalactosaminyltransferases, predominant, protein, regulation, response, Self Tolerance, signal, syndrome, T cell, tolerance, wild type
NCBI PubMed ID: 12183547Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: h.j.willison@udcf.gla.ac.uk
Institutions: University Department of Neurology, Institute of Neurological Sciences, Southern General Hospital, Glasgow, Scotland G51 4TF
Methods: ELISA
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2. Compound ID: 109
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a-Neup5Ac-(2-3)-+
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b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1--/Glcp(1-1)ceramide (ganglioside GM1) or the inner core-lipid A (lipopolysaccharide)/ |
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Structure type: oligomer
Aglycon: Glcp(1-1)ceramide (ganglioside GM1) or the inner core-lipid A (lipopolysaccharide)
Trivial name: ganglioside GM1
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_39,SB_68,SB_7,SB_8,SB_84,SB_88,SB_96
The structure is contained in the following publication(s):
- Article ID: 21
Bowes T, Wagner ER, Boffey J, Nicholl D, Cochrane L, Benboubetra M, Conner J, Furukawa K, Willison HJ "Tolerance to self gangliosides is the major factor restricting the antibody response to lipopolysaccharide core oligosaccharides in Campylobacter jejuni strains associated with Guillain-Barre syndrome" -
Infection and Immunity 70(9) (2002) 5008-5018
Guillain-Barre syndrome following Campylobacter jejuni infection is frequently associated with anti-ganglioside autoantibodies mediated by molecular mimicry with ganglioside-like oligosaccharides on bacterial lipopolysaccharide (LPS). The regulation of antibody responses to these T-cell-independent antigens is poorly understood, and only a minority of Campylobacter-infected individuals develop anti-ganglioside antibodies. This study investigates the response to gangliosides and LPS in strains of mice by using a range of immunization strategies. In normal mice following intraperitoneal immunization, antibody responses to gangliosides and LPS are low level but can be enhanced by the antigen format or coadministration of protein to recruit T-cell help. Class switching from the predominant immunoglobulin M (IgM) response to IgG3 occurs at low levels, suggesting B1-cell involvement. Systemic immunization results in poor responses. In GalNAc transferase knockout mice that lack all complex gangliosides and instead express high levels of GM3 and GD3, generation of anti-ganglioside antibodies upon immunization with either complex gangliosides or ganglioside-mimicking LPS is greatly enhanced and exhibits class switching to T-cell- dependent IgG isotypes and immunological memory, indicating that tolerance to self gangliosides is a major regulatory factor. Responses to GD3 are suppressed in knockout mice compared with wild-type mice, in which responses to GD3 are induced specifically by GD3 and as a result of polyclonal B-cell activation by LPS. The anti-ganglioside response generated in response to LPS is also dependent on the epitope density of the ganglioside mimicked and can be further manipulated by providing secondary signals via lipid A and CD40 ligation
Lipopolysaccharide, biosynthesis, antigen, lipopolysaccharides, LPS, oligosaccharide, core, chemistry, Bacterial, genetics, human, metabolism, pathogenicity, strain, molecular, transferase, antibodies, antibody, epitope, lipid, lipid A, Oligosaccharides, activation, animal, anti-ganglioside, antibody response, antigens, CD40, Autoantibodies, autoantibody, B cell, B-cell, Campylobacter, Campylobacter Infections, Campylobacter jejuni, Carbohydrate Sequence, class, complex, complications, core oligosaccharide, deficiency, density, enhanced, etiology, factor, Female, ganglioside, gangliosides, generation, Guillain-Barre syndrome, high, IgG, IgM, immunization, immunoglobulin, Immunoglobulin M, immunological, immunological memory, immunology, induced, infection, involvement, level, lipopolysaccharide core, lipopolysaccharide core oligosaccharide, liposomes, memory, mice, Inbred BALB C, Inbred C3H, Knockout, mimicry, molecular mimicry, Molecular Sequence Data, N-Acetylgalactosaminyltransferases, predominant, protein, regulation, response, Self Tolerance, signal, syndrome, T cell, tolerance, wild type
NCBI PubMed ID: 12183547Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: h.j.willison@udcf.gla.ac.uk
Institutions: University Department of Neurology, Institute of Neurological Sciences, Southern General Hospital, Glasgow, Scotland G51 4TF
Methods: ELISA
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3. Compound ID: 111
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a-Neup5Ac-(2-3)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1--/Glcp(1-1)ceramide (ganglioside GD1a) or the inner core-lipid A (lipopolysaccharide)/ |
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Structure type: oligomer
Aglycon: Glcp(1-1)ceramide (ganglioside GD1a) or the inner core-lipid A (lipopolysaccharide)
Trivial name: GD3
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_39,SB_68,SB_7,SB_70,SB_8,SB_84,SB_88,SB_96,SB_97
The structure is contained in the following publication(s):
- Article ID: 21
Bowes T, Wagner ER, Boffey J, Nicholl D, Cochrane L, Benboubetra M, Conner J, Furukawa K, Willison HJ "Tolerance to self gangliosides is the major factor restricting the antibody response to lipopolysaccharide core oligosaccharides in Campylobacter jejuni strains associated with Guillain-Barre syndrome" -
Infection and Immunity 70(9) (2002) 5008-5018
Guillain-Barre syndrome following Campylobacter jejuni infection is frequently associated with anti-ganglioside autoantibodies mediated by molecular mimicry with ganglioside-like oligosaccharides on bacterial lipopolysaccharide (LPS). The regulation of antibody responses to these T-cell-independent antigens is poorly understood, and only a minority of Campylobacter-infected individuals develop anti-ganglioside antibodies. This study investigates the response to gangliosides and LPS in strains of mice by using a range of immunization strategies. In normal mice following intraperitoneal immunization, antibody responses to gangliosides and LPS are low level but can be enhanced by the antigen format or coadministration of protein to recruit T-cell help. Class switching from the predominant immunoglobulin M (IgM) response to IgG3 occurs at low levels, suggesting B1-cell involvement. Systemic immunization results in poor responses. In GalNAc transferase knockout mice that lack all complex gangliosides and instead express high levels of GM3 and GD3, generation of anti-ganglioside antibodies upon immunization with either complex gangliosides or ganglioside-mimicking LPS is greatly enhanced and exhibits class switching to T-cell- dependent IgG isotypes and immunological memory, indicating that tolerance to self gangliosides is a major regulatory factor. Responses to GD3 are suppressed in knockout mice compared with wild-type mice, in which responses to GD3 are induced specifically by GD3 and as a result of polyclonal B-cell activation by LPS. The anti-ganglioside response generated in response to LPS is also dependent on the epitope density of the ganglioside mimicked and can be further manipulated by providing secondary signals via lipid A and CD40 ligation
Lipopolysaccharide, biosynthesis, antigen, lipopolysaccharides, LPS, oligosaccharide, core, chemistry, Bacterial, genetics, human, metabolism, pathogenicity, strain, molecular, transferase, antibodies, antibody, epitope, lipid, lipid A, Oligosaccharides, activation, animal, anti-ganglioside, antibody response, antigens, CD40, Autoantibodies, autoantibody, B cell, B-cell, Campylobacter, Campylobacter Infections, Campylobacter jejuni, Carbohydrate Sequence, class, complex, complications, core oligosaccharide, deficiency, density, enhanced, etiology, factor, Female, ganglioside, gangliosides, generation, Guillain-Barre syndrome, high, IgG, IgM, immunization, immunoglobulin, Immunoglobulin M, immunological, immunological memory, immunology, induced, infection, involvement, level, lipopolysaccharide core, lipopolysaccharide core oligosaccharide, liposomes, memory, mice, Inbred BALB C, Inbred C3H, Knockout, mimicry, molecular mimicry, Molecular Sequence Data, N-Acetylgalactosaminyltransferases, predominant, protein, regulation, response, Self Tolerance, signal, syndrome, T cell, tolerance, wild type
NCBI PubMed ID: 12183547Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: h.j.willison@udcf.gla.ac.uk
Institutions: University Department of Neurology, Institute of Neurological Sciences, Southern General Hospital, Glasgow, Scotland G51 4TF
Methods: ELISA
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4. Compound ID: 112
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a-Neup5Ac-(2-3)-+
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a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1--/Glcp(1-1)ceramide (ganglioside GT1a) or the inner core-lipid A (lipopolysaccharide)/ |
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Structure type: oligomer
Aglycon: Glcp(1-1)ceramide (ganglioside GT1a) or the inner core-lipid A (lipopolysaccharide)
Trivial name: GT1a
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_35,SB_39,SB_42,SB_68,SB_7,SB_70,SB_8,SB_84,SB_88,SB_96,SB_97
The structure is contained in the following publication(s):
- Article ID: 21
Bowes T, Wagner ER, Boffey J, Nicholl D, Cochrane L, Benboubetra M, Conner J, Furukawa K, Willison HJ "Tolerance to self gangliosides is the major factor restricting the antibody response to lipopolysaccharide core oligosaccharides in Campylobacter jejuni strains associated with Guillain-Barre syndrome" -
Infection and Immunity 70(9) (2002) 5008-5018
Guillain-Barre syndrome following Campylobacter jejuni infection is frequently associated with anti-ganglioside autoantibodies mediated by molecular mimicry with ganglioside-like oligosaccharides on bacterial lipopolysaccharide (LPS). The regulation of antibody responses to these T-cell-independent antigens is poorly understood, and only a minority of Campylobacter-infected individuals develop anti-ganglioside antibodies. This study investigates the response to gangliosides and LPS in strains of mice by using a range of immunization strategies. In normal mice following intraperitoneal immunization, antibody responses to gangliosides and LPS are low level but can be enhanced by the antigen format or coadministration of protein to recruit T-cell help. Class switching from the predominant immunoglobulin M (IgM) response to IgG3 occurs at low levels, suggesting B1-cell involvement. Systemic immunization results in poor responses. In GalNAc transferase knockout mice that lack all complex gangliosides and instead express high levels of GM3 and GD3, generation of anti-ganglioside antibodies upon immunization with either complex gangliosides or ganglioside-mimicking LPS is greatly enhanced and exhibits class switching to T-cell- dependent IgG isotypes and immunological memory, indicating that tolerance to self gangliosides is a major regulatory factor. Responses to GD3 are suppressed in knockout mice compared with wild-type mice, in which responses to GD3 are induced specifically by GD3 and as a result of polyclonal B-cell activation by LPS. The anti-ganglioside response generated in response to LPS is also dependent on the epitope density of the ganglioside mimicked and can be further manipulated by providing secondary signals via lipid A and CD40 ligation
Lipopolysaccharide, biosynthesis, antigen, lipopolysaccharides, LPS, oligosaccharide, core, chemistry, Bacterial, genetics, human, metabolism, pathogenicity, strain, molecular, transferase, antibodies, antibody, epitope, lipid, lipid A, Oligosaccharides, activation, animal, anti-ganglioside, antibody response, antigens, CD40, Autoantibodies, autoantibody, B cell, B-cell, Campylobacter, Campylobacter Infections, Campylobacter jejuni, Carbohydrate Sequence, class, complex, complications, core oligosaccharide, deficiency, density, enhanced, etiology, factor, Female, ganglioside, gangliosides, generation, Guillain-Barre syndrome, high, IgG, IgM, immunization, immunoglobulin, Immunoglobulin M, immunological, immunological memory, immunology, induced, infection, involvement, level, lipopolysaccharide core, lipopolysaccharide core oligosaccharide, liposomes, memory, mice, Inbred BALB C, Inbred C3H, Knockout, mimicry, molecular mimicry, Molecular Sequence Data, N-Acetylgalactosaminyltransferases, predominant, protein, regulation, response, Self Tolerance, signal, syndrome, T cell, tolerance, wild type
NCBI PubMed ID: 12183547Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: h.j.willison@udcf.gla.ac.uk
Institutions: University Department of Neurology, Institute of Neurological Sciences, Southern General Hospital, Glasgow, Scotland G51 4TF
Methods: ELISA
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5. Compound ID: 172
|
b-D-Glcp-(1-2)-+
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a-D-Galp-(1-2)-+ |
| |
a-Neup5Ac-(2-3)-+ | | /Variants 0/-+
| | | |
b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/
|
b-D-Glcp-(1-4)-+
/Variants 0/ is:
P-6)-
OR (exclusively)
EtN-(1--P--6)-- |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_131186,IEDB_134627,IEDB_135818,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_167072,IEDB_190606,IEDB_2189047,IEDB_742245,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_23,SB_24,SB_25,SB_39,SB_68,SB_7,SB_8,SB_84,SB_88,SB_96
The structure is contained in the following publication(s):
- Article ID: 37
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
- Article ID: 3821
Banoub JH, El Aneed A, Cohen AM, Joly N "Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry" -
Mass Spectrometry Reviews 29(4) (2010) 606-650
Mass spectrometric studies are now playing a leading role in the elucidation of lipopolysaccharide (LPS) structures through the characterization of antigenic polysaccharides, core oligosaccharides and lipid A components including LPS genetic modifications. The conventional MS and MS/MS analyses together with CID fragmentation provide additional structural information complementary to the previous analytical experiments, and thus contribute to an integrated strategy for the simultaneous characterization and correct sequencing of the carbohydrate moiety.
LPS, O-antigen, lipid A, core oligosaccharide, MS and MS/MS analyses
NCBI PubMed ID: 20589944Publication DOI: 10.1002/mas.20258Journal NLM ID: 8219702Publisher: Wiley
Correspondence: joe.banoub@dfo-mpo.gc.ca
Institutions: Fisheries and Oceans Canada, Science Branch, Special Projects, P.O. Box 5667, St. John's, Newfoundland, Canada A1C 5X1, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1B 3V6, College of Pharmacy and Nutrition, University of Saskatchewan, Thorvaldson Building, 110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9, Unité de Catalyse et de Chimie du Solide, Site de l'Artois—UMR CNRS 8181, I.U.T. de Béthune, Département Chimie, 1230 rue de l'Université, BP819, 62408 Béthune Cedex, France, Institute for Marine Biosciences Room 219A, (NRC-IMB), National Research Council of Canada, Government of Canada, 1411 Oxford Street, Halifax, NS, Canada B3H 3Z1
Methods: MS/MS, MS
- Article ID: 3869
Kabanov DS, Prokhorenko IR "Structural analysis of lipopolysaccharides from Gram-negative bacteria" -
Biochemistry (Moscow) 75(4) (2010) 383-404
This review covers data on composition and structure of lipid A, core, and O-polysaccharide of the known lipopolysaccharides from Gram-negative bacteria. The relationship between the structure and biological activity of lipid A is discussed. The data on roles of core and O-polysaccharide in biological activities of lipopolysaccharides are presented. The structural homology of some oligosaccharide sequences of lipopolysaccharides to gangliosides of human cell membranes is considered.
core, Lipooligosaccharide, O-antigen, lipid A, gangliosides, cytokines, lipopolysaccharide (endotoxin)
NCBI PubMed ID: 20618127Publication DOI: 10.1134/S0006297910040012Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: kabanovd1@rambler.ru
Institutions: Institute of Basic Biological Problems, Russian Academy of Sciences, Pushchino, Russia
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6. Compound ID: 257
|
-4)-a-D-Galp-(1-2)-b-D-Ribf-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-7)-D,D-3,9dthraltNon-onic-(2-6)-a-D-Glcp-(1-4)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149136,IEDB_151528,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_25,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 67
Faber EJ, Van Haaster DJ, Kamerling JP, Vliegenthart JF "Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid" -
European Journal of Biochemistry 269(22) (2002) 5590-5598
The exopolysaccharide produced by Streptococcus thermophilus 8S in reconstituted skimmed milk is a heteropolysaccharide containing d-galactose, d-glucose, d-ribose, and N-acetyl-d-galactosamine in a molar ratio of 2 : 1 : 1 : 1. Furthermore, the polysaccharide contains one equivalent of a novel open chain nononic acid constituent, 3,9-dideoxy-d-threo-d-altro-nononic acid, ether-linked via C-2 to C-6 of an additional d-glucose per repeating unit. Methylation analysis and 1D/2D NMR studies (1H and 13C) performed on the native polysaccharide, and mass spectrometric and NMR analyses of the oligosaccharide obtained from the polysaccharide by de-N-acetylation followed by deamination and reduction demonstrated the 'hepta'saccharide repeating unit to be: →4)-α-D-Galp-(1→2)-β-D-Ribf-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→7')-Sug-(1→4)-β-D-GalpNAc-(1→ in which Sug is 6-O-(3',9'-dideoxy-d-threo-d-altro-nononic acid-2'-yl)-α-D-glucopyranose
Lactic acid bacteria, Streptococcus thermophilus, exopolysaccharide, structural analysis, nononic acid
NCBI PubMed ID: 12423358Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: j.p.kamerling@chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Section of Glycoscience and Biocatalysis, Utrecht University, Utrecht, the Netherlands
Methods: methylation, NMR-2D, NMR, sugar analysis, MS, de-N-acetylation, deamination
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 5880
De Vuyst L, De Vin F "Exopolysaccharides from Lactic Acid Bacteria" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2007) 477-519
carbohydrates, Lactic acid bacteria, exopolysaccharides, polysaccharides, glycolipids, glycoproteins, Glycomics
Publication DOI: 10.1016/B978-044451967-2/00129-XPublisher: Elsevier
Correspondence: ldvuyst@vub.ac.be
Editors: Barchi J, Kamerling H
Institutions: Department of Applied Biological Sciences and Engineering, Research Group of Industrial Microbiology and Food Biotechnology, Vrije Universiteit Brussel, Brussels, Belgium
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7. Compound ID: 368
|
-4)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-4)-b-D-GalpNAc-(1-4)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_983931,SB_144,SB_165,SB_166,SB_187,SB_192,SB_195,SB_25,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 112
Toukach FV, Arbatsky NP, Shashkov AS, Knirel YA, Zych K, Sidorczyk Z "Structure of a neutral O-specific polysaccharide of Proteus penneri 34" -
Carbohydrate Research 312(1-2) (1998) 97-101
The O-specific polysaccharide of Proteus penneri strain 34 was studied using 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, and H-detected 1H, 13C HMQC experiments. The following structure was established, which is unique among the known structures of Proteus O-antigens: →4)-β-D-Glcp-(1→3)-β-D-GalpNAc-(1→4)-β-D-GalpNAc-(1→4)-β-D-Galp-(1→. Accordingly, no cross-reaction was observed between P. penneri 34 O-antiserum and O-antigens of other Proteus strains. Therefore, the strain studied should belong to a new Proteus serogroup O65.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, Proteus penneri
NCBI PubMed ID: 9836454Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland.
Methods: NMR-2D, NMR, serological methods
- Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis 52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
Lipopolysaccharide, structure, characterization, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, serological, O-serogroups, Ne-[(R)-1-carboxyethyl]-L-lysine
NCBI PubMed ID: 15053232Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
- Article ID: 1467
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry 73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
structure, O-antigen, Proteus, Bacterial polysaccharide, epitope specificity
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895Publisher: Państwowe Wydawnictwo Naukowe
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
- Article ID: 3257
Kolodziejska K, Siwinska M, Zych K, Rozalski A, Sidorczyk Z "Characterization and serological classification of O-specific polysaccharide of Proteus mirabilis TG 276-90 from Proteus serogroup O34" -
Archivum Immunologiae et Therapiae Experimentalis 54(3) (2006) 223-226
INTRODUCTION: Gram-negative bacteria of the genus Proteus from the family Enterobacteriaceae are currently divided into the five species P. mirabilis, P. vulgaris, P. penneri, P. hauseri, and P. myxofaciens and three unnamed Proteus genomospecies 4, 5, and 6. They are important facultative human and animal pathogens which, under favorable conditions, cause mainly intestinal and urinary tract infections, sometimes leading to serious complications such as acute or chronic pyelonephritis and the formation of bladder and kidney stones. In this study we report on the serological properties of the lipopolysaccharide (LPS) of P. mirabilis TG 276-90, whose O-polysaccharide chemical structure was described earlier. MATERIALS AND METHODS: LPS and alkali-treated LPS of a few serologically related Proteus strains and O-antisera against P. mirabilis TG 276-90 and CCUG 4669 (O34) were used. Serological characterization of P. mirabilis TG 276-90 O-specific polysaccharide was done using enzyme immunosorbent assay, passive immunohemolysis test (PIH), inhibition of these tests, SDS/PAGE and Western blot techniques, absorption of rabbit polyclonal O-antisera, and repeated PIH test. RESULTS: Structural and serological investigations showed that the O-polysaccharides of P. mirabilis TG 276-90 and P. vulgaris O34 are identical and that their LPSs differ only in epitopes in the core part. Therefore these two strains could be classified into the same Proteus O34 serogroup. CONCLUSIONS: The serological data showed that the β-D-GalpNAc-(1→4)-α-D-GalpNAc disaccharide is an important epitope of the P. mirabilis TG 276-90 and P. vulgaris O34 LPSs, shared by the P. mirabilis O16 and P. vulgaris TG 251 LPSs. It is responsible for cross-reactions with P. mirabilis TG 276-90 and P. vulgaris O34 O-antisera.
Lipopolysaccharide, O-antigen, Proteus mirabilis, Proteus vulgaris, O-serogroup
NCBI PubMed ID: 16736109Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: zsidor@biol.uni.lodz.pl
Institutions: Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237, Lodz, Poland
Methods: serological methods
- Article ID: 3311
Zych K, Kolodziejska K, Drzewiecka D, Perepelov AV, Knirel YA, Sidorczyk Z "Serological classification and epitope specificity of Proteus vulgaris TG 251 from Proteus serogroups O65" -
Archivum Immunologiae et Therapiae Experimentalis 55(3) (2007) 187-191
INTRODUCTION: Proteus rods are currently subdivided into five named species, i.e. Proteus mirabilis, P. vulgaris, P. penneri, P. hauseri, and P. myxofaciens, and three unnamed Proteus genomospecies 4 to 6. Based on the serospecificity of the lipopolysaccharide (LPS; O-antigen), strains of P. mirabilis and P. vulgaris were divided into 49 O-serogroups and 11 additional O-serogroups were proposed later. About 15 further O-serogroups have been proposed for the third medically important species, P. penneri. Here the serological classification of P. vulgaris strain TG 251, which does not belong to these serogroups, is reported. Serological investigations also allowed characterization of the epitope specificity of its LPS. MATERIALS AND METHODS: Purified LPSs from five Proteus strains were used as antigens in enzyme immunosorbent assay (EIA), SDS/PAGE, and Western blot and alkali-treated LPSs in the passive immunohemolysis (PIH) test, inhibition of PIH and EIA, and absorption of the rabbit polyclonal O-antisera with the respective LPS. RESULTS: The serological studies of P. vulgaris TG 251 LPS indicated the identity of its O-polysaccharide with that of P. penneri O65. The antibody specificities of P. vulgaris TG 251 and P. penneri O65 O-antisera, were described. CONCLUSIONS: P. vulgaris TG 251 was classified to the Proteus O65 serogroup. Two disaccharide-associated epitopes present in P. vulgaris TG 251 and P. penneri O65 LPSs are suggested to be responsible for cross-reactions with three heterologous Proteus strains.
Lipopolysaccharide, epitope, Proteus, serological classification, O-serogroup
NCBI PubMed ID: 17557147Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: zsidor@biol.uni.lodz.pl
Institutions: Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, SDS-PAGE, EIA, Western blotting
- Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology 120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
cancer, glycans, natural antibodies, anti-glycan antibodies, Tn antigen
NCBI PubMed ID: 32087569Publication DOI: 10.1016/j.molimm.2020.02.005Journal NLM ID: 7905289Publisher: Elsevier
Correspondence: professorbovin@yandex.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France
Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
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8. Compound ID: 552
|
b-D-GalpNAc-(1-3)-+
|
-6)-b-D-Glcp-(1-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: O-deacetylated and dephosphorylated polysaccharide (DPS)
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_983931,SB_192,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 114
Toukach FV, Shashkov AS "Computer-assisted structural analysis of regular glycopolymers on the basis of 13C NMR data" -
Carbohydrate Research 335(2) (2001) 101-104
A computer-assisted approach to the prediction of the primary structures of regular glycopolymers is described. The analysis is based on comparing the calculated 13C NMR spectra of all the possible structures of the repeating unit (for the given monomeric composition) to an experimental 13C NMR spectrum. The spectra generation is based on the spectral database containing information on the 13C chemical shifts of monomers, di- and trimeric fragments. If the required data are missing from this database, the special database for average glycosylation effects is used. The analysis reveals those structures with the calculated 13C NMR spectrum most close to observed. The structures of repeating units of any topology containing up to six residues linked by glycosidic, amidic or phospho-diester bridges can be predicted. Unambiguous selection of the proper structure from the output list of possible structures may require additional experimental data. Testing the created program and databases on bacterial polysaccharides and their derivatives containing up to three non-sugar residues (alditols, amino acids, phosphate groups etc.) per repeating unit revealed the good convergence of prediction with independently obtained structural data.
NMR, structural, analysis, structural analysis, 13C NMR, calculation, computer, glycopolymer, regular
NCBI PubMed ID: 11567641Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tou@cacr.ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation.
Methods: NMR simulation
- Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis 52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
Lipopolysaccharide, structure, characterization, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens, serological, O-serogroups, Ne-[(R)-1-carboxyethyl]-L-lysine
NCBI PubMed ID: 15053232Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: rozala@biol.uni.lodz.pl
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
- Article ID: 890
Kondakova AN, Toukach FV, Senchenkova SN, Arbatsky NP, Shashkov AS, Knirel YA, Zych K, Torzewska A, Kolodziejska K, Rozalski A, Sidorczyk Z "New structures of the O-specific polysaccharides of Proteus. Part 2. O-Acetylated polysaccharides" -
Biochemistry (Moscow) 67(2) (2002) 201-211
Structures of five new O-specific polysaccharides of Proteus bacteria were established. Four of them, Proteus penneri 4 (O72), Proteus vulgaris 63/57 (O37), Proteus mirabilis TG 277 (O69), and Proteus penneri 20 (O17), contain O-acetyl groups in non-stoichiometric quantities, and the polysaccharide of P. penneri 1 is structurally related to that of P. penneri 4. The structures were elucidated using NMR spectroscopy, including one dimensional 1H- and 13C-NMR spectroscopy, two-dimensional 1H, 1H correlation (COSY, TOCSY), H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY or ROESY), along with chemical methods. The structural data obtained are useful as the chemical basis for the creation of the classification scheme for Proteus strains.
structure, Bacterial, polysaccharide, O-antigen, O-specific, O-specific polysaccharide, Proteus, polysaccharides, O-specific polysaccharides, O-acetyl
Publication DOI: 10.1023/A:1014414030784Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR, de-O-acetylation
- Article ID: 1238
Sidorczyk Z, Toukach FV, Zych K, Drzewiecka D, Arbatsky NP, Shashkov AS, Knirel YA "Structural and serological relatedness of the O-antigens of Proteus penneri 1 and 4 from a novel Proteus serogroup O72" -
European Journal of Biochemistry 269(1) (2002) 358-363
O-specific polysaccharides (O-antigens) of the lipopolysaccharides (LPS) of Proteus penneri strains 1 and 4 were studied using sugar analysis, (1)H and (13)C NMR spectroscopy, including 2D COSY, H-detected (1)H,(13)C HMQC, and rotating-frame NOE spectroscopy (ROESY). The following structures of the tetrasaccharide (strain 1) and pentasaccharide (strain 4) repeating units of the polysaccharides were established: [reaction: see text]. In the polysaccharide of P. penneri strain 4, glycosylation with the lateral Glc residue (75%) and O-acetylation of the lateral GalNAc residue (55%) are nonstoichiometric. This polysaccharide contains also other, minor O-acetyl groups, whose positions were not determined. The structural similarity of the O-specific polysaccharides was consistent with the close serological relatedness of the LPS, which was demonstrated by immunochemical studies with O-antisera against P. penneri 1 and 4. Based on these data, it was proposed to classify P. penneri strains 1 and 4 into a new Proteus serogroup, O72, as two subgroups, O72a and O72a,b, respectively. Serological cross-reactivity of P. penneri 1 O-antiserum with the LPS of P. penneri 40 and 41 was substantiated by the presence of an epitope(s) on the LPS core region shared by all P. penneri strains studied.
Lipopolysaccharide, O-antigen, O-specific polysaccharide, Proteus penneri, O-serogroup
NCBI PubMed ID: 11784330Publication DOI: 10.1046/j.0014-2956.2001.02660.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: zsidor@biol.uni.lodz.pl
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology and Immunology, University of Łodź, Łodź, Poland
Methods: NMR
- Article ID: 3357
Perepelov AV, Liu B, Senchenkova SN, Shevelev SD, Wang W, Shashkov AS, Feng L, Wang L, Knirel YA "The structure of the glycerol phosphate-containing O-specific polysaccharide from Escherichia coli O130" -
Russian Journal of Bioorganic Chemistry 33(1) (2007) 64-68
A phosphorylated O-specific polysaccharide was obtained by mild acidic degradation of the lipopolysaccharide from the enteric bacterium Escherichia coli O130 and characterized by the methods of chemical analysis, including dephosphorylation and 1H and 13C NMR spectroscopy. The polysaccharide was shown to be composed of branched tetrasaccharide repeating units containing two N-acetyl-D-galactosamine residues,D-galactose, D-glucose,and glycerophosphate residues (one of each). The polysaccharide has the following structure, which is unique among the known bacterial polysaccharides:
Escherichia coli, O-specific polysaccharide, teichoic acid, glycerophosphate, structure; NMR spectroscopy
Publication DOI: 10.1134/S1068162007010062Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Correspondence: knirel@ioc.ac.ru
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia,TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, China Tyan-jin Key Laboratory for Microbial Functional Genomics, TEDA College, Nankai University, TEDA, Tyan-jin, China
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, GLC, mild acid hydrolysis, NMR-1D
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9. Compound ID: 555
|
R-CetEtN-(1--P--6)--+
|
-4)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_144988,IEDB_144989,IEDB_144990,IEDB_151528,IEDB_167071,IEDB_190606,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 114
Toukach FV, Shashkov AS "Computer-assisted structural analysis of regular glycopolymers on the basis of 13C NMR data" -
Carbohydrate Research 335(2) (2001) 101-104
A computer-assisted approach to the prediction of the primary structures of regular glycopolymers is described. The analysis is based on comparing the calculated 13C NMR spectra of all the possible structures of the repeating unit (for the given monomeric composition) to an experimental 13C NMR spectrum. The spectra generation is based on the spectral database containing information on the 13C chemical shifts of monomers, di- and trimeric fragments. If the required data are missing from this database, the special database for average glycosylation effects is used. The analysis reveals those structures with the calculated 13C NMR spectrum most close to observed. The structures of repeating units of any topology containing up to six residues linked by glycosidic, amidic or phospho-diester bridges can be predicted. Unambiguous selection of the proper structure from the output list of possible structures may require additional experimental data. Testing the created program and databases on bacterial polysaccharides and their derivatives containing up to three non-sugar residues (alditols, amino acids, phosphate groups etc.) per repeating unit revealed the good convergence of prediction with independently obtained structural data.
NMR, structural, analysis, structural analysis, 13C NMR, calculation, computer, glycopolymer, regular
NCBI PubMed ID: 11567641Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: tou@cacr.ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation.
Methods: NMR simulation
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10. Compound ID: 729
|
R-3HOBut-(1-3)-b-D-Fucp3N-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-+
|
-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-6)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_147450,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_742248,IEDB_885822,SB_163,SB_165,SB_166,SB_187,SB_195,SB_21,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 194
Vinogradov EV, Pantophlet R, Dijkshoorn L, Brade L, Holst O, Brade H "Structural and serological characterisation of two O-specific polysaccharides of Acinetobacter" -
European Journal of Biochemistry 239 (1996) 602-610
Extraction of dry bacteria of Acinetobacter strain 34 (DNA group 2) or Acinetobacter strain 108 (DNA group 13) by phenol/water yielded a polymer that was identified by means of serological studies and fatty acid analysis as S-form lipopolysaccharide. Degradation of the lipopolysaccharides of strains 34 and 108 in 1% acetic acid and 5% acetic acid, respectively, and gel-permeation chromatography gave the respective O-antigenic polysaccharides, the structures of which were determined, by compositional analysis and NMR spectroscopy of the polysaccharide, as [Sequence: see text] for strain 108, where D-Fucp3NBuOH represents 3-[(R)-3-hydroxybutyramido] -3,6-dideoxy-D-galactose and D-GalpANAc represents 2-acetamido-2-deoxy-D-galacturonic acid. Both structures were specifically recognised in Western blots by polyclonal rabbit antisera and there was no cross-reaction between these two structures.
Lipopolysaccharide, NMR, Acinetobacter, serology, Western blot
NCBI PubMed ID: 8774703Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Department of Medical Microbiology, Leiden University Hospital, Leiden, The Netherlands
Methods: NMR-2D, NMR, composition analysis
- Article ID: 681
Haseley SR, Wilkinson SG "Structural studies of the putative O-specific polysaccharide of Acinetobacter baumannii O2 containing 3,6-dideoxy-3-N-(D-3-hydroxybutyryl)amino-D-galactose" -
European Journal of Biochemistry 233 (1995) 899-906
A polysaccharide containing D-galactose, 2-deoxy-2-N-acetylamino-D-galactose and 3,6-dideoxy-3-N-(D-3-hydroxybutyryl)amino-D-galactose, probably corresponding to the lipopolysaccharide side chain, was obtained from an aqueous phenol extract of isolated cell walls from Acinetobacter baumannii strain O2. By means of NMR studies and chemical degradations, the repeating unit of the polymer was identified as a branched hexasaccharide of the structure shown, where Fuc3N represents 3-amino-3,6-dideoxygalactose and R represents D-3-hydroxybutyryl. Serological tests indicated that the polymer corresponded to the O2 antigen.
Lipopolysaccharide, Acinetobacter, Acinetobacter baumannii, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-amino-3, 3-hydroxybutyric acid
NCBI PubMed ID: 8521857Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: School of Chemistry, University of Hull, England.
Methods: methylation, NMR-2D, partial acid hydrolysis, NMR, Smith degradation
- Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4534
Hu D, Liu B, Dijkshoorn L, Wang L, Reeves PR "Diversity in the major polysaccharide antigen of Acinetobacter baumannii assessed by DNA sequencing, and development of a molecular serotyping scheme" -
PLoS One 8(7) (2013) e70329
We have sequenced the gene clusters for type strains of the Acinetobacter baumannii serotyping scheme developed in the 1990s, and used the sequences to better understand diversity in surface polysaccharides of the genus. We obtained genome sequences for 27 available serovar type strains, and identified 25 polysaccharide gene cluster sequences. There are structures for 12 of these polysaccharides, and in general the genes present are appropriate to the structure where known. This greatly facilitates interpretation. We also find 53 different glycosyltransferase genes, and for 7 strains can provisionally allocate specific genes to all linkages. We identified primers that will distinguish the 25 sequence forms by PCR or microarray, or alternatively the genes can be used to determine serotype by 'molecular serology'. We applied the latter to 190 Acinetobacter genome-derived gene-clusters, and found 76 that have one of the 25 gene-cluster forms. We also found novel gene clusters and added 52 new gene-cluster sequence forms with different wzy genes and different gene contents. Altogether, the strains that have one of the original 25 sequence forms include 98 A. baumannii (24 from our strains) and 5 A. nosocomialis (3 from our strains), whereas 32 genomes from 12 species other than A. baumannii or A. nosocomialis, all have new sequence forms. One of the 25 serovar type sequences is found to be in European clone I (EC I), 2 are in EC II but none in EC III. The public genome strains add an additional 52 new sequence forms, and also bring the number found in EC I to 5, in EC II to 9 and in EC III to 2.
antigen, structure, Acinetobacter baumannii, gene cluster, glycosyltransferase, serotyping, genome, surface polysaccharide, polysaccharide antigen
NCBI PubMed ID: 23922982Publication DOI: 10.1371/journal.pone.0070329Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Peter R. Reeves
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China, Department of Infectious Diseases, Leiden University Medical Center, Leiden, The Netherlands, School of Molecular Bioscience, University of Sydney, Sydney, Australia
Methods: PCR, DNA sequencing, DNA techniques, genetic methods
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
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11. Compound ID: 731
|
R-3HOBut-(1-3)-b-D-Fucp3N-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-+
|
-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-3)-D-Gro-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_885822,SB_21,SB_25,SB_7
The structure is contained in the following publication(s):
- Article ID: 194
Vinogradov EV, Pantophlet R, Dijkshoorn L, Brade L, Holst O, Brade H "Structural and serological characterisation of two O-specific polysaccharides of Acinetobacter" -
European Journal of Biochemistry 239 (1996) 602-610
Extraction of dry bacteria of Acinetobacter strain 34 (DNA group 2) or Acinetobacter strain 108 (DNA group 13) by phenol/water yielded a polymer that was identified by means of serological studies and fatty acid analysis as S-form lipopolysaccharide. Degradation of the lipopolysaccharides of strains 34 and 108 in 1% acetic acid and 5% acetic acid, respectively, and gel-permeation chromatography gave the respective O-antigenic polysaccharides, the structures of which were determined, by compositional analysis and NMR spectroscopy of the polysaccharide, as [Sequence: see text] for strain 108, where D-Fucp3NBuOH represents 3-[(R)-3-hydroxybutyramido] -3,6-dideoxy-D-galactose and D-GalpANAc represents 2-acetamido-2-deoxy-D-galacturonic acid. Both structures were specifically recognised in Western blots by polyclonal rabbit antisera and there was no cross-reaction between these two structures.
Lipopolysaccharide, NMR, Acinetobacter, serology, Western blot
NCBI PubMed ID: 8774703Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Department of Medical Microbiology, Leiden University Hospital, Leiden, The Netherlands
Methods: NMR-2D, NMR, composition analysis
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12. Compound ID: 871
|
a-Neup5Ac-(2-3)-+
|
b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_39,SB_68,SB_7,SB_8,SB_84,SB_88,SB_96
The structure is contained in the following publication(s):
- Article ID: 243
Goodyear CS, O'Hanlon GM, Plomp JJ, Wagner ER, Morrison I, Veitch J, Cochrane L, Bullens RWM, Molenaar PC, Conner J, Willison HJ "Monoclonal antibodies raised against Guillain-Barre syndrome- associated Campylobacter jejuni lipopolysaccharides react with neuronal gangliosides and paralyze muscle-nerve preparations" -
Journal of Clinical Investigation 104(6) (1999) 697-708
Guillain-Barre syndrome and its variant, Miller-Fisher syndrome, are acute, postinfectious, autoimmune neuropathies that frequently follow Campylobacter jejuni enteritis. The pathogenesis is believed to involve molecular mimicry between sialylated epitopes on C. jejuni LPSs and neural gangliosides. More than 90% of Miller-Fisher syndrome cases have serum anti-GQ1b and anti-GT1a ganglioside antibodies that may also react with other disialylated gangliosides including GD3 and GD1b. Structural studies on LPS from neuropathy-associated C. jejuni strains have revealed GT1a-like and GD3-like core oligosaccharides. To determine whether this structural mimicry results in pathogenic autoantibodies, we immunized mice with GT1a/GD3-like C. jejuni LPS and then cloned mAb's that reacted with both the immunizing LPS and GQ1b/GT1a/GD3 gangliosides. Immunohistology demonstrated antibody binding to ganglioside-rich sites including motor nerve terminals. In ex vivo electrophysiological studies of nerve terminal function, application of antibodies either ex vivo or in vivo via passive immunization induced massive quantal release of acetylcholine, followed by neurotransmission block. This effect was complement-dependent and associated with extensive deposits of IgM and C3c at nerve terminals. These data provide strong support for the molecular mimicry hypothesis as a mechanism for the induction of cross-reactive pathogenic anti-ganglioside/LPS antibodies in postinfectious neuropathies
Lipopolysaccharide, lipopolysaccharides, antibodies, antibody, monoclonal, monoclonal antibodies, monoclonal antibody, Campylobacter, Campylobacter jejuni, ganglioside, gangliosides, syndrome, preparation, neuronal
NCBI PubMed ID: 10491405Journal NLM ID: 7802877Publisher: Ann Arbor, MI: American Society for Clinical Investigation
Correspondence: gora13@udcf.gla.ac.uk
Institutions: University Department of Neurology, Southern General Hospital, Glasgow G51 4TF, Scotland, Department of Biological Sciences, Glasgow Caledonian University, Glasgow G4 OBA, Scotland, Department of Neurology, Department of Physiology, Leiden University Medical Centre, 2300 RC Leiden, the Netherlands
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13. Compound ID: 873
|
a-Neup5Ac-(2-3)-+
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a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_35,SB_39,SB_42,SB_68,SB_7,SB_70,SB_8,SB_84,SB_88,SB_96,SB_97
The structure is contained in the following publication(s):
- Article ID: 243
Goodyear CS, O'Hanlon GM, Plomp JJ, Wagner ER, Morrison I, Veitch J, Cochrane L, Bullens RWM, Molenaar PC, Conner J, Willison HJ "Monoclonal antibodies raised against Guillain-Barre syndrome- associated Campylobacter jejuni lipopolysaccharides react with neuronal gangliosides and paralyze muscle-nerve preparations" -
Journal of Clinical Investigation 104(6) (1999) 697-708
Guillain-Barre syndrome and its variant, Miller-Fisher syndrome, are acute, postinfectious, autoimmune neuropathies that frequently follow Campylobacter jejuni enteritis. The pathogenesis is believed to involve molecular mimicry between sialylated epitopes on C. jejuni LPSs and neural gangliosides. More than 90% of Miller-Fisher syndrome cases have serum anti-GQ1b and anti-GT1a ganglioside antibodies that may also react with other disialylated gangliosides including GD3 and GD1b. Structural studies on LPS from neuropathy-associated C. jejuni strains have revealed GT1a-like and GD3-like core oligosaccharides. To determine whether this structural mimicry results in pathogenic autoantibodies, we immunized mice with GT1a/GD3-like C. jejuni LPS and then cloned mAb's that reacted with both the immunizing LPS and GQ1b/GT1a/GD3 gangliosides. Immunohistology demonstrated antibody binding to ganglioside-rich sites including motor nerve terminals. In ex vivo electrophysiological studies of nerve terminal function, application of antibodies either ex vivo or in vivo via passive immunization induced massive quantal release of acetylcholine, followed by neurotransmission block. This effect was complement-dependent and associated with extensive deposits of IgM and C3c at nerve terminals. These data provide strong support for the molecular mimicry hypothesis as a mechanism for the induction of cross-reactive pathogenic anti-ganglioside/LPS antibodies in postinfectious neuropathies
Lipopolysaccharide, lipopolysaccharides, antibodies, antibody, monoclonal, monoclonal antibodies, monoclonal antibody, Campylobacter, Campylobacter jejuni, ganglioside, gangliosides, syndrome, preparation, neuronal
NCBI PubMed ID: 10491405Journal NLM ID: 7802877Publisher: Ann Arbor, MI: American Society for Clinical Investigation
Correspondence: gora13@udcf.gla.ac.uk
Institutions: University Department of Neurology, Southern General Hospital, Glasgow G51 4TF, Scotland, Department of Biological Sciences, Glasgow Caledonian University, Glasgow G4 OBA, Scotland, Department of Neurology, Department of Physiology, Leiden University Medical Centre, 2300 RC Leiden, the Netherlands
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14. Compound ID: 881
|
b-D-Glcp-(1-2)-+
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a-D-Galp-(1-2)-+ |
| |
a-Neup5Ac-(2-3)-+ | | EtN-(1--P--6)--+
| | | |
b-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
|
b-D-Glcp-(1-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: LOS, LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_167072,IEDB_190606,IEDB_2189047,IEDB_742245,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_25,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 248
Guerry P, Ewing CP, Hickey TE, Prendergast MM, Moran AP "Sialylation of lipooligosaccharide cores affects immunogenicity and serum resistance of Campylobacter jejuni" -
Infection and Immunity 68(12) (2000) 6656-6662
Three genes involved in biosynthesis of the lipooligosaccharide (LOS) core of Campylobacter jejuni MSC57360, the type strain of the HS:1 serotype, whose structure mimics GM(2) ganglioside, have been cloned and characterized. Mutation of genes encoding proteins with homology to a sialyl transferase (cstII) and a putative N-acetylmannosamine synthetase (neuC1), part of the biosynthetic pathway of N-acetylneuraminic acid (NeuNAc), have identical phenotypes. The LOS cores of these mutants display identical changes in electrophoretic mobility, loss of reactivity with cholera toxin (CT), and enhanced immunoreactivity with a hyperimmune polyclonal antiserum generated against whole cells of C. jejuni MSC57360. Loss of sialic acid in the core of the neuC1 mutant was confirmed by fast atom bombardment mass spectrometry. Mutation of a gene encoding a putative β-1,4-N-acetylgalactosaminyltransferase (Cgt) resulted in LOS cores intermediate in electrophoretic mobility between that of wild type and the mutants lacking NeuNAc, loss of reactivity with CT, and a reduced immunoreactivity with hyperimmune antiserum. Chemical analyses confirmed the loss of N-acetylgalactosamine (GalNAc) and the presence of NeuNAc in the cgt mutant. These data suggest that the Cgt enzyme is capable of transferring GalNAc to an acceptor with or without NeuNAc and that the Cst enzyme is capable of transferring NeuNAc to an acceptor with or without GalNAc. A mutant with a nonsialylated LOS core is more sensitive to the bactericidal effects of human sera than the wild type or the mutant lacking GalNAc
core, Lipooligosaccharide, Campylobacter, Campylobacter jejuni, immunogenicity, resistance, serum, serum resistance, sialylation
NCBI PubMed ID: 11083778Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: guerryp@nmrc.navy.mil
Institutions: Enteric Diseases Department, Naval Medical Research Center, Silver Spring, Maryland 20910, USA, Department of Microbiology, National University of Ireland, Galway, Ireland
- Article ID: 2442
Aspinall GO, McDonald AG, Raju TS, Pang H, Moran AP, Penner JL "Chemical structures of the core regions of Campylobacter jejuni serotypes O:1, O:4, O:23, and O:36 lipopolysaccharides" -
European Journal of Biochemistry 213 (1993) 1017-1027
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
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15. Compound ID: 884
|
b-D-Galp-(1-2)-+
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a-D-Galp-(1-2)-+ | EtN-(1--P--6)--+
| | |
b-D-GalpNAc-(1-4)-b-D-Galp-(1-3)-b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
|
b-D-Glcp-(1-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_167072,IEDB_190606,IEDB_2189047,IEDB_742245,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_25,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 248
Guerry P, Ewing CP, Hickey TE, Prendergast MM, Moran AP "Sialylation of lipooligosaccharide cores affects immunogenicity and serum resistance of Campylobacter jejuni" -
Infection and Immunity 68(12) (2000) 6656-6662
Three genes involved in biosynthesis of the lipooligosaccharide (LOS) core of Campylobacter jejuni MSC57360, the type strain of the HS:1 serotype, whose structure mimics GM(2) ganglioside, have been cloned and characterized. Mutation of genes encoding proteins with homology to a sialyl transferase (cstII) and a putative N-acetylmannosamine synthetase (neuC1), part of the biosynthetic pathway of N-acetylneuraminic acid (NeuNAc), have identical phenotypes. The LOS cores of these mutants display identical changes in electrophoretic mobility, loss of reactivity with cholera toxin (CT), and enhanced immunoreactivity with a hyperimmune polyclonal antiserum generated against whole cells of C. jejuni MSC57360. Loss of sialic acid in the core of the neuC1 mutant was confirmed by fast atom bombardment mass spectrometry. Mutation of a gene encoding a putative β-1,4-N-acetylgalactosaminyltransferase (Cgt) resulted in LOS cores intermediate in electrophoretic mobility between that of wild type and the mutants lacking NeuNAc, loss of reactivity with CT, and a reduced immunoreactivity with hyperimmune antiserum. Chemical analyses confirmed the loss of N-acetylgalactosamine (GalNAc) and the presence of NeuNAc in the cgt mutant. These data suggest that the Cgt enzyme is capable of transferring GalNAc to an acceptor with or without NeuNAc and that the Cst enzyme is capable of transferring NeuNAc to an acceptor with or without GalNAc. A mutant with a nonsialylated LOS core is more sensitive to the bactericidal effects of human sera than the wild type or the mutant lacking GalNAc
core, Lipooligosaccharide, Campylobacter, Campylobacter jejuni, immunogenicity, resistance, serum, serum resistance, sialylation
NCBI PubMed ID: 11083778Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: guerryp@nmrc.navy.mil
Institutions: Enteric Diseases Department, Naval Medical Research Center, Silver Spring, Maryland 20910, USA, Department of Microbiology, National University of Ireland, Galway, Ireland
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