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Structure type: homopolymer
Compound class: O-polysaccharide, O-antigen

• Article ID: 175
  Vinogradov E, Peppler MS, Perry MB "The structure of the nonreducing terminal groups in the O-specific polysaccharides from two strains of Bordetella bronchiseptica" - European Journal of Biochemistry 267(24) (2000) 7230-7236
  

  The structures of the polysaccharide chains of the LPS from Bordetella bronchiseptica strains 110H and Bp512 were analysed by NMR spectroscopy and mass spectrometry. The polysaccharides consist of α-(1-4)-linked 2,3-diacetamido-2,3-dideoxy-L-galacturonic acid repeating units. Polysaccharides from both strains have 2,3,4-triamino-2,3,4-trideoxy-α-galacturonamide derivatives at their nonreducing ends, a monosaccharide identified for the first time in nature. The polymers from the two strains differ in the nature of the acylation of the amino groups of this monosaccharide. In the strain 110H, the residue is formylated at positions 3 and 4, and has N-formyl-L-alanyl or L-alanyl substituents at N-2. In the strain Bp512, the amino group at position 2 is acetylated, at position 3 it is formylated, and the amino group at position 4 bears a 2-methoxypropionyl substituent. The distribution of the acyl groups was determined from long range 1H-13C correlation (HMBC) NMR spectra. Measurement of the spectra under different pH conditions showed that carboxyl groups of the inner uronic acid residues of the polymeric chain are free, and that carboxyl groups of the terminal residues are amidated. These conclusions were confirmed by the results of mass spectrometric analysis.

  LPS, structure, strain, terminal, polysaccharide, O-antigen, group, O-specific, O-specific polysaccharide, Bordetella, polysaccharides, Bordetella bronchiseptica, nonreducing, O-specific polysaccharides

  NCBI PubMed ID: 11106436
  Publication DOI: 10.1046/j.1432-1327.2000.01835.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: evguenii.vinogradov@nrc.ca
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Medical Microbiology and Immunology, University of Alberta, Edmonton, AB, Canada
  Methods: NMR-2D, NMR, chemical methods, MS
  
   
  
  Bordetella bronchiseptica Bp512, Bordetella bronchiseptica 110H
  CSDB ID 5779 (all data & tools)
• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Bordetella bronchiseptica, Bordetella parapertussis
  CSDB ID 108417 (all data & tools)
• Article ID: 3269
  Preston A, Petersen BO, Duus JO, Kuebler-Kielb J, Ben Menachem G, Li J, Vinogradov E "Complete structure of Bordetella bronchiseptica and Bordetella parapertussis lipopolysaccharides" - Journal of Biological Chemistry 281(26) (2006) 18135-18144
  

  The structure of the carbohydrate part of the LPS from several strains of Bordetella bronchiseptica and Bordetella parapertussis was analyzed using different chemical degradations, NMR spectroscopy and mass spectrometry. It was found that, in addition to previously known structures of the core and O-chain, all studied LPSs contain a specific pentasaccharide fragment linking these two structural regions. This fragment is attached to 'band A' trisaccharide in B. bronchiseptica LPS and to the core GlcN in B. parapertussis LPS. LPSs from different strains contain variable amount of amidated diaminouronic acids in the polysaccharide chain. Together with previously known structural details these new data present a complete structure of the LPS carbohydrate backbone for both bordetellae species. Two types of O-chain terminal monosaccharide have been found in all analyzed strains of B. bronchiseptica, and only one of them in B. parapertussis LPS

  Lipopolysaccharide, NMR spectroscopy, mass spectrometry, Bordetella bronchiseptica, Bordetella parapertussis

  NCBI PubMed ID: 16632471
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: evguenii.vinogradov@nrc-cnrc.gc.ca
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A OR6, Canada, Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Carlsberg Laboratory, DK 2500 Valby Copenhagen, Denmark, NICHD, National Institutes of Health, Bethesda, MD, USA
  Methods: NMR, HF solvolysis, sugar analysis, MS, deamination
  
   
  
  Bordetella bronchiseptica, Bordetella parapertussis
  CSDB ID 20412 (all data & tools)
• Article ID: 3498
  Kubler-Kielb J, Vinogradov E, Ben Menachem G, Pozsgay V, Robbins JB, Schneerson R "Saccharide/protein conjugate vaccines for Bordetella species: Preparation of saccharide, development of new conjugation procedures, and physico-chemical and immunological characterization of the conjugates" - Vaccine 26(29-30) (2008) 3587-3593
  

  Bordetellae are Gram-negative bacilli causing respiratory tract infections of mammals and birds. Clinically important are B. pertussis, B. parapertussis and B. bronchiseptica. B. pertussis vaccines have been successful in preventing pertussis in infants and children. Veterinary vaccines against B. bronchiseptica are available, but their efficacy and mode of action are not established. There is no vaccine against B. parapertussis. Based on the concept that immunity to non-capsulated Gram-negative bacteria may be conferred by serum IgG anti-LPS we studied chemical, serological and immunological properties of the O-specific polysaccharides (O-SP) of B. bronchiseptica and B. parapertussis obtained by different degradation procedures. One type of the B. parapertussis and two types of B. bronchiseptica O-SP were recognized based on the structure of their non-reducing end saccharide; no cross-reaction between the two B. bronchiseptica types was observed. Competitive inhibition assays showed the immunodominance of the non-reducing end of these O-SP. Conjugates of B. bronchiseptica and B. parapertussis O-SP were prepared by two methods: using the anhydro-Kdo residue exposed by mild acid hydrolysis of the LPS or the 2,5-anhydromannose residue exposed by deamination of the core glucosamine of the LPS, for binding to an aminooxylated protein. Both coupling methods were carried out at a neutral pH, room temperature, and in a short time. All conjugates, injected as saline solutions at a fraction of an estimated human dose, induced antibodies in mice to the homologous O-SP. These methodologies can be applied to prepare O-SP-based vaccines against other Gram-negative bacteria

  LPS, Bordetella, O-specific polysaccharides, vaccine, conjugate

  NCBI PubMed ID: 18539367
  Publication DOI: 10.1016/j.vaccine.2008.04.079
  Journal NLM ID: 8406899
  Publisher: Elsevier
  Correspondence: J. Kubler-Kielb
  Institutions: National Institute of Child Health and Human Development, National Institutes of Health, 9000 Rockville Pike, Bethesda, MD, USA
  Methods: HF solvolysis, SDS-PAGE, acid hydrolysis, MALDI-TOF MS, serological methods
  
   
  
  Bordetella bronchiseptica 10580
  CSDB ID 22679 (all data & tools)
• 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: 20618127
  Publication DOI: 10.1134/S0006297910040012
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: kabanovd1@rambler.ru
  Institutions: Institute of Basic Biological Problems, Russian Academy of Sciences, Pushchino, Russia
  
   
  
  Bordetella bronchiseptica 110H, Bordetella bronchiseptica Bp5132
  CSDB ID 25690 (all data & tools)
• Article ID: 3960
  Vinogradov E, King JD, Pathak AK, Harvill ET, Preston A "Antigenic Variation among Bordetella: Bordetella bronchiseptica strain MO149 expresses a novel O chain that is poorly immunogenic" - Journal of Biological Chemistry 285(35) (2010) 26869-26877
  

  The O chain polysaccharide (O PS) of Bordetella bronchiseptica and Bordetella parapertussis lipopolysaccharide is a homopolymer of 2,3-diacetamido-2,3-dideoxygalacturonic acid (GalNAc3NAcA) in which some of the sugars are present as uronamides. The terminal residue contains several unusual modifications. To date, two types of modification have been characterized, and a survey of numerous strains demonstrated that each contained one of these two modification types. Host antibody responses against the O PS are directed against the terminal residue modifications, and there is little cross-reactivity between the two types. This suggests that Bordetella O PS modifications represent a means of antigenic variation. Here we report the characterization of the O PS of B. bronchiseptica strain MO149. It consists of a novel two-sugar repeating unit and a novel terminal residue modification, with the structure Me-4-α-L-GalNAc3NAcA-(4-β-D-GlcNAc3NAcA-4-α-L-GalNAc3NAcA-)(5-6)-, which we propose be defined as the B. bronchiseptica O3 PS. We show that the O3 PS is very poorly immunogenic and that the MO149 strain contains a novel wbm (O PS biosynthesis) locus. Thus, there is greater diversity among Bordetella O PSs than previously recognized, which is likely to be a result of selection pressure from host immunity. We also determine experimentally, for the first time, the absolute configuration of the diacetimido-uronic acid sugars in Bordetella O PS.

  O polysaccharide, bacteria, Bordetella, immunity, lipopolysaccharide (LPS), evolution, Bacterial Genetics, Humoral Response

  NCBI PubMed ID: 20592026
  Publication DOI: 10.1074/jbc.M110.115121
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: a.preston@bristol.ac.uk
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A 0R6, Canada
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, HF solvolysis, sugar analysis, ESI-MS, mild acid hydrolysis, Western blotting, serological methods, genetic methods
  
   
  
  Bordetella bronchiseptica O1, Bordetella bronchiseptica O2
  CSDB ID 25877 (all data & tools)
• Article ID: 4307
  Greenfield LK, Whitfield C "Synthesis of lipopolysaccharide O-antigens by ABC transporter-dependent pathways" - Carbohydrate Research 356 (2012) 12-24
  

  The O-polysaccharide (O-PS; O-antigen) of bacterial lipopolysaccharides is made up of repeating units of one or more sugar residues and displays remarkable structural diversity. Despite the structural variations, there are only three strategies for O-PS assembly. The ATP-binding cassette (ABC)-transporter-dependent mechanism of O-PS biosynthesis is widespread. The Escherichia coli O9a and Klebsiella pneumoniae O2a antigens provide prototypes, which are distinguished by the fine details that link glycan polymerization and chain termination at the cytoplasmic face of the inner membrane to its export via the ABC transporter. Here, we describe the current understanding of these processes. Since glycoconjugate assembly complexes that utilize an ABC transporter-dependent pathway are widespread among the bacterial kingdom, the models described here are expected to extend beyond O-PS biosynthesis systems

  Lipopolysaccharide, O-polysaccharide, ATP-binding cassette transporter, Escherichia coli O9a, Klebsiella pneumoniae O2a

  NCBI PubMed ID: 22475157
  Publication DOI: 10.1016/j.carres.2012.02.027
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: C. Whitfield
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1
  
   
  
  Bordetella bronchiseptica RB50, Bordetella parapertussis BAA-587 ATCC 12822
  CSDB ID 28356 (all data & tools)

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Structure type: monomer
Aglycon: core
Trivial name: non reducing end-group of O-polysaccharide
Compound class: O-polysaccharide

• Article ID: 3498
  Kubler-Kielb J, Vinogradov E, Ben Menachem G, Pozsgay V, Robbins JB, Schneerson R "Saccharide/protein conjugate vaccines for Bordetella species: Preparation of saccharide, development of new conjugation procedures, and physico-chemical and immunological characterization of the conjugates" - Vaccine 26(29-30) (2008) 3587-3593
  

  Bordetellae are Gram-negative bacilli causing respiratory tract infections of mammals and birds. Clinically important are B. pertussis, B. parapertussis and B. bronchiseptica. B. pertussis vaccines have been successful in preventing pertussis in infants and children. Veterinary vaccines against B. bronchiseptica are available, but their efficacy and mode of action are not established. There is no vaccine against B. parapertussis. Based on the concept that immunity to non-capsulated Gram-negative bacteria may be conferred by serum IgG anti-LPS we studied chemical, serological and immunological properties of the O-specific polysaccharides (O-SP) of B. bronchiseptica and B. parapertussis obtained by different degradation procedures. One type of the B. parapertussis and two types of B. bronchiseptica O-SP were recognized based on the structure of their non-reducing end saccharide; no cross-reaction between the two B. bronchiseptica types was observed. Competitive inhibition assays showed the immunodominance of the non-reducing end of these O-SP. Conjugates of B. bronchiseptica and B. parapertussis O-SP were prepared by two methods: using the anhydro-Kdo residue exposed by mild acid hydrolysis of the LPS or the 2,5-anhydromannose residue exposed by deamination of the core glucosamine of the LPS, for binding to an aminooxylated protein. Both coupling methods were carried out at a neutral pH, room temperature, and in a short time. All conjugates, injected as saline solutions at a fraction of an estimated human dose, induced antibodies in mice to the homologous O-SP. These methodologies can be applied to prepare O-SP-based vaccines against other Gram-negative bacteria

  LPS, Bordetella, O-specific polysaccharides, vaccine, conjugate

  NCBI PubMed ID: 18539367
  Publication DOI: 10.1016/j.vaccine.2008.04.079
  Journal NLM ID: 8406899
  Publisher: Elsevier
  Correspondence: J. Kubler-Kielb
  Institutions: National Institute of Child Health and Human Development, National Institutes of Health, 9000 Rockville Pike, Bethesda, MD, USA
  Methods: HF solvolysis, SDS-PAGE, acid hydrolysis, MALDI-TOF MS, serological methods
  
   
  
  Bordetella bronchiseptica 10580
  CSDB ID 23030 (all data & tools)