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1. Compound ID: 727
R-3HOBut-(1-3)-b-D-Fucp3N-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-+
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-3)-b-D-GalpNAc-(1-4)-a-D-Galp-(1-6)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, CPS
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: 193
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: 680
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: NMR-2D, methylation, partial acid hydrolysis, NMR, Smith degradation
- Article ID: 4328
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: 4533
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 metods
- 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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2. Compound ID: 729
R-3HOBut-(1-3)-b-D-Fucp3N-(1-3)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-+
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-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: 193
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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3. Compound ID: 1460
L-gro-a-D-manHepp-(1-2)-+
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EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+
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b-D-Glcp-(1-4)-+ |
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a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdo
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a-D-Glcp-(1-6)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 464
St-Michael F, Vinogradov E, Li J, Cox AD "Structural analysis of the lipopolysaccharide from Pasteurella multocida genome strain Pm70 and identification of the putative lipopolysaccharide glycosyltransferases" -
Glycobiology 15(4) (2005) 323-333
Pasteurella multocida is an important multi-species veterinary pathogen. The cell surface lipopolysaccharide (LPS) is an important virulence factor and forms the basis of the serotyping scheme, although little structural information about the LPS is known. The structure of the LPS from the Pasteurella multocida genome strain Pm70 was elucidated in this study. The LPS was subjected to a variety of degradative procedures. The structures of the purified products were established by monosaccharide and methylation analyses, NMR spectroscopy and mass spectrometry. The following structure for the core oligosaccharide was determined on the basis of the combined data from these experiments, where based on the NMR data all sugars were found in pyranose ring forms. Glucose, galactose and N-acetyl-galactosamine residues were all present as D-isomers. Kdo is 2-keto-3-deoxy-octulosonic acid, L-α-D-Hep is L-glycero-D-manno-heptose, and PEtn is phosphoethanolamine. Identification of the core oligosaccharide structure enabled a search for glycosyltransferase homologues in the Pm70 genome, and revealed a clustering of the genes putatively responsible for outer core oligosaccharide biosynthesis.
Lipopolysaccharide, NMR, core oligosaccharide, mass spectrometry, nuclear magnetic resonance, Pasteurella multocida
NCBI PubMed ID: 15537789Publication DOI: 10.1093/glycob/cwi015Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: andrew.cox@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, K1A 0R6, Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, K1A 0R6
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, 31P NMR, ESI-MS, GLC, CE-MS
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4. Compound ID: 7590
?%EtN-(1---P---P---4)-+
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L-gro-a-D-manHepp-(1-2)-+ |
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EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+ |
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b-D-Glcp-(1-4)-+ | |
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a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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a-D-Glcp-(1-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: inner core glycoform A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3398
Harper M, Cox A, St-Michael F, Parnas H, Wilkie I, Blackall PJ, Adler B, Boyce JD "Decoration of Pasteurella multocida LPS with phosphocholine is important for virulence" -
Journal of Bacteriology 189(20) (2007) 7384-7391
Phosphocholine (PCho) is an important substituent of surface structures expressed by a number of bacterial pathogens. Its role in virulence has been investigated in several species, in which it has been shown to play a role in bacterial adhesion to mucosal surfaces, resistance to antimicrobial peptides or sensitivity to complement-mediated killing. The lipopolysaccharide (LPS) structure of the Pasteurella multocida strain Pm70, whose genome sequence is known, has recently been determined and does not contain PCho. However, the LPS structures from the closely related, virulent P. multocida strains VP161 and X-73 were shown to contain PCho on their terminal galactose sugar residues. To determine if PCho was involved in virulence in P. multocida, we used subtractive hybridisation of the VP161 genome against the Pm70 genome to identify a four-gene locus (designated pcgDABC) which we show is required for addition of the PCho residues to LPS. The proteins predicted to be encoded by pcgABC showed identity to proteins involved in choline uptake, phosphorylation and nucleotide sugar activation of PCho. We constructed a mutant in the P. multocida VP161 pcgC gene and demonstrated that this strain produces LPS that lacks PCho on the terminal galactose residues. This pcgC mutant displayed reduced in vivo growth in a chicken infection model and was more sensitive to the chicken antimicrobial peptide fowlicidin-1 than wild-type P. multocida
Lipopolysaccharide, Phosphocholine, phosphorylation, Pasteurella multocida
NCBI PubMed ID: 17704225Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: harvil@psu.edu
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada K1A OR6, Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Department of Microbiology, Monash University, Melbourne, Australia, Veterinary Pathology and Anatomy, University of Queensland, Brisbane, Queensland 4072, Australia, Department of Primary Industries and Fisheries (Queensland) Animal Research Institute, Yeerongpilly, Queensland 4105, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, GLC, composition analysis, NMR-1D, serological methods, genetic methods, immunoblotting, CE-ESI-MS, acid degradation
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5. Compound ID: 7591
L-gro-a-D-manHepp-(1-2)-+
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EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+
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b-D-Glcp-(1-4)-+ | a-Kdop-(2-4)-+
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a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-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
Trivial name: inner core glycoform B
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3398
Harper M, Cox A, St-Michael F, Parnas H, Wilkie I, Blackall PJ, Adler B, Boyce JD "Decoration of Pasteurella multocida LPS with phosphocholine is important for virulence" -
Journal of Bacteriology 189(20) (2007) 7384-7391
Phosphocholine (PCho) is an important substituent of surface structures expressed by a number of bacterial pathogens. Its role in virulence has been investigated in several species, in which it has been shown to play a role in bacterial adhesion to mucosal surfaces, resistance to antimicrobial peptides or sensitivity to complement-mediated killing. The lipopolysaccharide (LPS) structure of the Pasteurella multocida strain Pm70, whose genome sequence is known, has recently been determined and does not contain PCho. However, the LPS structures from the closely related, virulent P. multocida strains VP161 and X-73 were shown to contain PCho on their terminal galactose sugar residues. To determine if PCho was involved in virulence in P. multocida, we used subtractive hybridisation of the VP161 genome against the Pm70 genome to identify a four-gene locus (designated pcgDABC) which we show is required for addition of the PCho residues to LPS. The proteins predicted to be encoded by pcgABC showed identity to proteins involved in choline uptake, phosphorylation and nucleotide sugar activation of PCho. We constructed a mutant in the P. multocida VP161 pcgC gene and demonstrated that this strain produces LPS that lacks PCho on the terminal galactose residues. This pcgC mutant displayed reduced in vivo growth in a chicken infection model and was more sensitive to the chicken antimicrobial peptide fowlicidin-1 than wild-type P. multocida
Lipopolysaccharide, Phosphocholine, phosphorylation, Pasteurella multocida
NCBI PubMed ID: 17704225Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: harvil@psu.edu
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada K1A OR6, Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Department of Microbiology, Monash University, Melbourne, Australia, Veterinary Pathology and Anatomy, University of Queensland, Brisbane, Queensland 4072, Australia, Department of Primary Industries and Fisheries (Queensland) Animal Research Institute, Yeerongpilly, Queensland 4105, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, GLC, composition analysis, NMR-1D, serological methods, genetic methods, immunoblotting, CE-ESI-MS, acid degradation
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6. Compound ID: 7657
b-D-Glcp-(1-3)-+
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-3)-a-D-Galp-(1-6)-a-D-Galp-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_144989,IEDB_146664,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_885822,IEDB_983931,SB_163,SB_192,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 3429
Ali T, Weintraub A, Widmalm G "Structural determination of the O-antigenic polysaccharide from Escherichia coli O166" -
Carbohydrate Research 342(2) (2007) 274-278
The O-antigen of the lipopolysaccharide from Escherichia coli O166 has been determined by component analysis together with 1D and 2D NMR spectroscopy techniques. The polysaccharide has pentasaccharide repeating units consisting of d-glucose (1), d-galactose (2) and N-acetyl-d-galactosamine (2) with the following structure: In the (1)H NMR, spectrum resonances of low intensity were observed. Further analysis of these showed that they originate from the terminal part of the polysaccharide, thereby revealing that the repeating unit has a 3-substituted N-acetyl-d-galactosamine residue at its reducing end
Lipopolysaccharide, NMR, Escherichia coli, biological repeating unit
NCBI PubMed ID: 17182015Publication DOI: 10.1016/j.carres.2006.11.023Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, Karolinska University Hospital, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, NMR-1D, serological methods
- Article ID: 3890
Liu B, Perepelov AV, Li D, Senchenkova SN, Han Y, Shashkov AS, Feng L, Knirel YA, Wang L "Structure of the O-antigen of Salmonella O66 and the genetic basis for similarity and differences between the closely related O-antigens of Escherichia coli O166 and Salmonella O66" -
Microbiology (2010) 1642-1649
O-antigen is a component of the outer membrane of Gram-negative bacteria and is one of the most variable cell surface constituents, leading to major antigenic variability. The O-antigen forms the basis for bacterial serotyping. In this study, the O-antigen structure of Salmonella O66 was established, which differs from the known O-antigen structure of Escherichia coli O166 only in one linkage (most likely the linkage between the O-units) and O-acetylation. The O-antigen gene clusters of Salmonella O66 and E. coli O166 were found to have similar organizations, the only exception being that in Salmonella O66, the wzy gene is replaced by a non-coding region. The function of the wzy gene in E. coli O166 was confirmed by the construction and analysis of deletion and trans-complementation mutants. It is proposed that a functional wzy gene located outside the O-antigen gene cluster is involved in Salmonella O66 O-antigen biosynthesis, as has been reported previously in Salmonella serogroups A, B and D1. The sequence identity for the corresponding genes between the O-antigen gene clusters of Salmonella O66 and E. coli O166 ranges from 64 to 70 %, indicating that they may originate from a common ancestor. It is likely that after the species divergence, Salmonella O66 got its specific O-antigen form by inactivation of the wzy gene located in the O-antigen gene cluster and acquisition of two new genes (a wzy gene and a prophage gene for O-acetyl modification) both residing outside the O-antigen gene cluster.
structure, O-antigen, Escherichia, O-acetylation, Salmonella enterica, Escherichia coli O166, Salmonella O66, O-antigen gene clusters
NCBI PubMed ID: 20185508Publication DOI: 10.1111/j.1574-695X.2010.00738.xJournal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: wanglei@nankai.edu.cn
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 HongDa Street, TEDA, Tianjin, China, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, Tianjin Research Center for Functional Genomics and Biochip, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, PR China
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, GLC, de-O-acetylation, NMR-1D, genetic methods
- Article ID: 5472
Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" -
FEMS Microbiology Reviews 44(6) (2020) 655-683
Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.
structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity
NCBI PubMed ID: 31778182Publication DOI: 10.1093/femsre/fuz028Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: G. Widmalm
; Lei Wang
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
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7. Compound ID: 8421
L-gro-a-D-manHepp-(1-2)-+
|
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+
|
b-D-Glcp-(1-4)-+ | EtN-(1---P---P---4)-+
| | |
a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-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_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3667
Boyce JD, Harper M, St-Michael F, John M, Aubry A, Parnas H, Logan SM, Wilkie IW, Ford M, Cox AD, Adler B "Identification of novel glycosyltransferases required for assembly of the Pasteurella multocida A:1 lipopolysaccharide and their involvement in virulence" -
Infection and Immunity 77(4) (2009) 1532-1542
We previously determined the structure of the Pasteurella multocida Heddleston type 1 lipopolysaccharide (LPS) molecule and characterized some of the transferases essential for LPS biosynthesis. We also showed that P. multocida strains expressing truncated LPS display reduced virulence. Here, we have identified all of the remaining glycosyltransferases required for synthesis of the oligosaccharide extension of the P. multocida Heddleston type 1 LPS, including a novel α-1,6 glucosyltransferase, a β-1,4 glucosyltransferase, a putative bifunctional galactosyltransferase, and two heptosyltransferases. In addition, we identified a novel oligosaccharide extension expressed only in a heptosyltransferase (hptE) mutant background. All of the analyzed mutants expressing LPS with a truncated main oligosaccharide extension displayed reduced virulence, but those expressing LPS with an intact heptose side chain were able to persist for long periods in muscle tissue. The hptC mutant, which expressed LPS with the shortest oligosaccharide extension and no heptose side chain, was unable to persist on the muscle or cause any disease. Furthermore, all of the mutants displayed increased sensitivity to the chicken antimicrobial peptide fowlicidin 1, with mutants expressing highly truncated LPS being the most sensitive
Lipopolysaccharide, biosynthesis, virulence, glycosyltransferases, Pasteurella multocida, chickens
NCBI PubMed ID: 19168738Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: Ben.Adler@med.monash.edu.au
Institutions: Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Monash University, Melbourne, Australia
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, ESI-MS, composition analysis, genetic methods, CE-MS, mild hydrazinolysis
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8. Compound ID: 9502
Structure type: oligomer
Trivial name: Forssman antigen
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_144987,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_742247,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_21,SB_31,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4032
Harper M, Cox AD, Adler B, Boyce JD "Pasteurella multocida lipopolysaccharide: The long and the short of it" -
Veterinary Microbiology 153(1-2) (2011) 109-115
Pasteurella multocida is a capsulated, Gram-negative cocco-bacillus that can cause serious disease in a wide range of mammals and birds. P. multocida strains are classified into 16 serovars based on lipopolysaccharide (LPS) antigens. LPS is an essential virulence factor of P. multocida; mutants expressing severely truncated LPS are completely attenuated in chickens. LPS is also a major immunogen of P. multocida and protection against infections caused by P. multocida is generally considered to be serovar specific. In this review we summarize current knowledge of the structure and genetics of LPS assembly of P. multocida strains belonging to five different serovars. These include strains belonging to serovars 1 and 3, the most common serovars found in the poultry industry, and strains belonging serovars 2 and 5, the serovars associated with bovine haemorrhagic septicaemia outbreaks. A number of the serovars are genetically related; serovars 1 and 14 share the same LPS outer core biosynthesis locus, but due to a mutation within the phosphocholine biosynthesis gene, pcgA, the serovar 14 strain produces a truncated LPS structure. Similarly serovars 2 and 5 share an identical LPS outer core locus and express near-identical LPS structures. However, due to a single point mutation in the phosphoethanolamine (PEtn) transferase gene, lpt_3, the serovar 2 strain does not elaborate a PEtn residue on heptose II. Knowledge of the genetic basis for the LPS structures expressed by P. multocida will facilitate the development of rapid molecular methods for typing and diagnosis and will be essential for a rational approach to vaccine formulation.
Lipopolysaccharide, virulence, glycosyltransferase, Pasteurella multocida
NCBI PubMed ID: 21664074Publication DOI: 10.1016/j.vetmic.2011.05.022Journal NLM ID: 7705469Publisher: Amsterdam; Elsevier
Correspondence: B. Adler
Institutions: Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Monash University, Melbourne, Australia
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9. Compound ID: 11212
EtN-(1-0)-?%P---P--4)-+
|
L-gro-a-D-manHepp-(1-2)-+ |
| |
EtN-(1-0)-?%P-3)-L-gro-a-D-manHepp-(1-3)-+ |
| |
b-D-Glcp-(1-4)-+ | |
| | |
a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-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: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4529
Harper M, St Michael F, John M, Vinogradov E, van Dorsten L, Steen JA, Turni C, Blackall PJ, Adler B, Cox AD, Boyce JD "Pasteurella multocida Heddleston serovar 3 and 4 strains share a common lipopolysaccharide biosynthesis locus but display both inter- and intra-strain lipopolysaccharide heterogeneity" -
Journal of Bacteriology 195(21) (2013) 4854-4864
Pasteurella multocida is a Gram-negative multi-species pathogen and the causative agent of fowl cholera, a serious disease of poultry which can present in both acute and chronic forms. The major outer membrane component lipopolysaccharide (LPS) is both an important virulence factor and a major immunogen. Our previous studies have determined the LPS structures expressed by different P. multocida strains and revealed that a number of strains belonging to different serovars contain the same LPS biosynthesis locus but express different LPS structures due to mutations within glycosyltransferase genes. In this study we report the full LPS structure of the serovar 4 type strain, P1662, and reveal that it shares the same LPS outer core biosynthesis locus, L3, with the serovar 3 strains, P1059 and Pm70. Using directed mutagenesis, the role of each glycosyltransferase gene in LPS outer core assembly has been determined. LPS structural analysis of 23 Australian field isolates that contain the L3 locus reveal that at least six different LPS outer core structures can be produced as a result of mutations within the LPS glycosyltransferase genes. Moreover, some field isolates produce multiple but related LPS glycoforms simultaneously and three LPS outer core structures are remarkably similar to the globo series of vertebrate glycosphingolipids. Our in-depth analysis showing the genetics and full range of P. multocida lipopolysaccharide structures will facilitate the improvement of typing systems and the prediction of the protective efficacy of vaccines.
Lipopolysaccharide, biosynthesis, genetics, virulence factor, Pasteurella multocida, typing
NCBI PubMed ID: 23974032Publication DOI: 10.1128/JB.00779-13Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: john.boyce@monash.edu
Institutions: Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Department of Microbiology, Monash University, Melbourne, Australia
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, de-O-acylation, SDS-PAGE, DNA techniques, 31P NMR, ESI-MS, CE-MS, sugar analyis
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10. Compound ID: 11215
b-D-Glcp-(1-4)-+
|
a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-gro-a-D-manHepp-(1--/inner core/ |
Show graphically |
Structure type: oligomer
Aglycon: inner core
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4529
Harper M, St Michael F, John M, Vinogradov E, van Dorsten L, Steen JA, Turni C, Blackall PJ, Adler B, Cox AD, Boyce JD "Pasteurella multocida Heddleston serovar 3 and 4 strains share a common lipopolysaccharide biosynthesis locus but display both inter- and intra-strain lipopolysaccharide heterogeneity" -
Journal of Bacteriology 195(21) (2013) 4854-4864
Pasteurella multocida is a Gram-negative multi-species pathogen and the causative agent of fowl cholera, a serious disease of poultry which can present in both acute and chronic forms. The major outer membrane component lipopolysaccharide (LPS) is both an important virulence factor and a major immunogen. Our previous studies have determined the LPS structures expressed by different P. multocida strains and revealed that a number of strains belonging to different serovars contain the same LPS biosynthesis locus but express different LPS structures due to mutations within glycosyltransferase genes. In this study we report the full LPS structure of the serovar 4 type strain, P1662, and reveal that it shares the same LPS outer core biosynthesis locus, L3, with the serovar 3 strains, P1059 and Pm70. Using directed mutagenesis, the role of each glycosyltransferase gene in LPS outer core assembly has been determined. LPS structural analysis of 23 Australian field isolates that contain the L3 locus reveal that at least six different LPS outer core structures can be produced as a result of mutations within the LPS glycosyltransferase genes. Moreover, some field isolates produce multiple but related LPS glycoforms simultaneously and three LPS outer core structures are remarkably similar to the globo series of vertebrate glycosphingolipids. Our in-depth analysis showing the genetics and full range of P. multocida lipopolysaccharide structures will facilitate the improvement of typing systems and the prediction of the protective efficacy of vaccines.
Lipopolysaccharide, biosynthesis, genetics, virulence factor, Pasteurella multocida, typing
NCBI PubMed ID: 23974032Publication DOI: 10.1128/JB.00779-13Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: john.boyce@monash.edu
Institutions: Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Department of Microbiology, Monash University, Melbourne, Australia
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, de-O-acylation, SDS-PAGE, DNA techniques, 31P NMR, ESI-MS, CE-MS, sugar analyis
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11. Compound ID: 11593
EtN-(1-0)-?%P---P--4)-+
|
L-gro-a-D-manHepp-(1-2)-+ |
| |
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+ |
| |
b-D-Glcp-(1-4)-+ | |
| | |
a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-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_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4680
Harper M, St Michael F, John M, Steen J, van Dorsten L, Parnas H, Vinogradov E, Adler B, Cox AD, Boyce JD "Structural analysis of lipopolysaccharide produced by Heddleston serovars 10, 11, 12 and 15 and the identification of a new Pasteurella multocida LPS outer core biosynthesis locus, L6" -
Glycobiology 24(7) (2014) 649-659
Pasteurella multocida is a Gram-negative bacterial pathogen classified into 16 serovars based on lipopolysaccharide (LPS) antigens. Previously, we have characterised the LPS outer core biosynthesis loci L1, L2, L3, L5 and L7, and have elucidated the full range of LPS structures associated with each. In this study, we have determined the LPS structures produced by the type strains representing the serovars 10, 11, 12 and 15 and characterized a new LPS outer core biosynthesis locus, L6, common to all. The L6 outer core biosynthesis locus shares significant synteny with the L3 locus but due to nucleotide divergence, gene duplication, and gene redundancy, the L6 and L3 LPS outer cores are structurally distinct. Using LPS structural and genetic differences identified in each L6 strain we have predicted a role for most of the L6 glycosyltransferases in LPS assembly. Importantly, we have identified two glycosyltransferases, GctD and GatB, that differ by one amino acid, A162T, but use different donor sugars (UDP-Glc and UDP-Gal respectively). The longest outer core oligosaccharide, produced by the serovar 12 type strain, contained a terminal region consisting of β-Gal-(1,4)-β-GlcNAc-(1,3)-β-Gal-(1,4)-β-Glc that was identical in structure to the vertebrate glycosphingolipid, paragloboside. Mimicry of host glycosphingolipids has been observed previously in P. multocida strains belonging to L3 LPS genotype, which produce LPS similar in structure to the globo-series of glycosphingolipids. The expression of a paragloboside-like oligosaccharide on the LPS produced by the serovar 12 type strain indicates that strains belonging to the L6 LPS genotype may also engage in molecular mimicry.
LPS, structure, gene, genetics, core oligosaccharide, glycosyltransferases, glycosyltransferase, Pasteurella multocida, glycosphingolipid
NCBI PubMed ID: 24740556Publication DOI: 10.1093/glycob/cwu030Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: marina.harper@monash.edu
Institutions: Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Monash University, Melbourne, Australia
Methods: 13C NMR, 1H NMR, PCR, GLC-MS, de-O-acylation, sugar analysis, DNA techniques, genetic methods, biochemical methods, CE-ESI-MS, bioinformatic analysis
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12. Compound ID: 11704
b-D-Glcp-(1-3)-+
|
-3)-a-D-Galp-(1-6)-a-D-Galp-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_144989,IEDB_146664,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_885822,IEDB_983931,SB_163,SB_192,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 4696
Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Reeves P, Wang L "Structural diversity in Salmonella O antigens and its genetic basis" -
FEMS Microbiology Reviews 38(1) (2014) 56-89
This review covers the structures and genetics of the 46 O antigens of Salmonella, a major pathogen of humans and domestic animals. The variation in structures underpins the serological specificity of the 46 recognized serogroups. The O antigen is important for the full function and virulence of many bacteria, and the considerable diversity of O antigens can confer selective advantage. Salmonella O antigens can be divided into two major groups: those which have N-acetylglucosamine (GlcNAc) or N-acetylgalactosamine (GalNAc) and those which have galactose (Gal) as the first sugar in the O unit. In recent years, we have determined 21 chemical structures and sequenced 28 gene clusters for GlcNAc-/GalNAc-initiated O antigens, thus completing the structure and DNA sequence data for the 46 Salmonella O antigens. The structures and gene clusters of the GlcNAc-/GalNAc-initiated O antigens were found to be highly diverse, and 24 of them were found to be identical or closely related to Escherichia coli O antigens. Sequence comparisons indicate that all or most of the shared gene clusters were probably present in the common ancestor, although alternative explanations are also possible. In contrast, the better-known eight Gal-initiated O antigens are closely related both in structures and gene cluster sequences.
polysaccharide, glycosyltransferase, pathogen, serotyping, evolution, polymorphism
NCBI PubMed ID: 23848592Publication DOI: 10.1111/1574-6976.12034Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: wanglei@nankai.edu.cn
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, Tianjin Research Center for Functional Genomics and Biochip, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia
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13. Compound ID: 11912
EtN-(1-0)-?%P---P--4)-+
|
L-gro-a-D-manHepp-(1-2)-+ |
| |
?%EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-+ |
| |
b-D-Glcp-(1-4)-+ | |
| | |
a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-L-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_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4756
Harper M, St Michael F, Steen JA, John M, Wright A, van Dorsten L, Vinogradov E, Adler B, Cox AD, Boyce JD "Characterization of the lipopolysaccharide produced by Pasteurella multocida serovars 6, 7 and 16: Identification of lipopolysaccharide genotypes L4 and L8" -
Glycobiology 25(3) (2015) 294-302
Pasteurella multocida is an important veterinary pathogen that produces a wide range of lipopolysaccharide (LPS) structures, many of which mimic host glycoproteins. In this study, we complete our analysis of the LPS produced by the P. multocida Heddleston serovars by reporting the LPS structure and the LPS outer core biosynthesis loci of the type strains representing Heddleston serovars 6, 7 and 16. Genetic analysis revealed that the type strains representing serovars 6 and 7 share the same LPS outer core biosynthesis locus which we have designated LPS genotype L4. Comparative bioinformatic analysis revealed that although the serovar 16 type strain contained a different LPS locus, L8, there was a significant degree of nucleotide identity between the L4 and L8 loci. Structural analysis revealed that the LPS glycoforms produced by the L4 and L8 strains all contained the highly conserved inner core produced by all other P. multocida strains examined to date. The residues within the LPS outer core produced by the L4 and L8 strains were either Gal or derivatives of Gal; unlike all other P. multocida Heddleston type strains examined there are no heptosyltransferases encoded in the L4 and L8 outer core biosynthesis loci. The structure of the L4 LPS outer core produced by the serovar 6 type strain consisted of β-Gal-(1-3)-β-N-acetylgalactosamine (GalNAc)-(1-4)-β-GalNAc3OAc-(1-4)-α-GalNAc3OAc-(1-3)-β-Gal, whereas the serovar 7 type strain produced a highly truncated LPS outer core containing only a single β-Gal residue. The structure of the L8 LPS outer core produced by the serovar 16 type strain consisted of β-Gal-(1-3)-β-GalNAc-(1-4)-(α-GalNAc-(1-3)-)-α-GalNAc.
LPS, structure, genetics, core oligosaccharide, Pasteurella multocida
NCBI PubMed ID: 25298538Publication DOI: 10.1093/glycob/cwu110Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: marina.harper@monash.edu
Institutions: Department of Microbiology, Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON, Canada K1A 0R6, Department of Microbiology, Monash University, Building 76, Melbourne, Australia
Methods: 13C NMR, 1H NMR, methylation, PCR, DNA sequencing, GLC-MS, de-O-acylation, sugar analysis, 31P NMR, GLC, MS/MS, CE-ESI-MS, bioinformatic analysis
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14. Compound ID: 12253
b-D-Glcp-(1-3)-+
|
-3)-a-D-Galp-(1-6)-a-D-Galp-(1-4)-a-D-GalpNAc-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_144989,IEDB_146664,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_885822,IEDB_983931,SB_163,SB_192,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 4876
Wittmann A, Lamprinaki D, Bowels KM, Katzenellenbogen E, Knirel YA, Nishimura K, Matsumoto N, Yamamoto K, Iwakura Y, Saijo S, Kawasaki N "Dectin-2 recognises an O-antigen polysaccharide from a human opportunistic pathogen and augments LPS activation of myeloid cells" -
Journal of Biological Chemistry 291(34) (2016) 17629-17638
LPS consists of a relatively conserved region of lipid A and core oligosaccharide and a highly variable region of O-antigen polysaccharide. Whereas lipid A is known to bind to the Toll-like receptor 4 (TLR4)-myeloid differentiation factor 2 (MD2) complex, the role of the O-antigen remains unclear. Here we report a novel molecular interaction between dendritic cell-associated C-type lectin-2 (Dectin-2) and mannosylated O-antigen found in a human opportunistic pathogen, Hafnia alvei PCM 1223, which has a repeating unit of [-Man-?1,3-Man-?1,2-Man-?1,2-Man-?1,2-Man-?1,3-]. H. alvei LPS induced higher levels of TNF? and IL-10 from mouse bone marrow-derived dendritic cells (BM-DCs), when compared with Salmonella enterica O66 LPS, which has a repeat of [-Gal-?1,6-Gal-?1,4-[Glc-?1,3]GalNAc-?1,3-GalNAc-?1,3-]. In a cell-based reporter assay, Dectin-2 was shown to recognize H. alvei LPS. This binding was inhibited by mannosidase treatment of H. alvei LPS and by mutations in the carbohydrate-binding domain of Dectin-2, demonstrating that H. alvei LPS is a novel glycan ligand of Dectin-2. The enhanced cytokine production by H. alvei LPS was Dectin-2-dependent, because Dectin-2 knock-out BM-DCs failed to do so. This receptor cross-talk between Dectin-2 and TLR4 involved events including spleen tyrosine kinase (Syk) activation and receptor juxtaposition. Furthermore, another mannosylated LPS from Escherichia coli O9a also bound to Dectin-2 and augmented TLR4 activation of BM-DCs. Taken together, these data indicate that mannosylated O-antigens from several Gram-negative bacteria augment TLR4 responses through interaction with Dectin-2.
polysaccharide, immunology, lectin, lipopolysaccharide (LPS), Toll-like receptor 4 (TLR4)
NCBI PubMed ID: 27358401Publication DOI: 10.1074/jbc.M116.741256Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: norihito.kawasaki@ifr.ac.uk
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Norwich Medical School, University of East Anglia, Norwich NR4 7TJ, United Kingdom, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw 53-114, Poland, Center for Animal Disease Models, Research Institute for Biomedical Sciences, Tokyo University of Science, Chiba 278-0022, Japan, Department of Molecular Immunology, Medical Mycology Research Center, Chiba University, Chiba 260-8673, Japan, Food and Health Institute Strategic Programme, Institute of Food Research, Norwich NR4 7UA, United Kingdom, Department of Integrated Biosciences, Graduate School of Frontier Sciences, University of Tokyo, Chiba 277-8562, Japan
Methods: ELISA, Western blotting, biological assays, binding assays, Dectin-2 reporter assay
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