Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, LPS
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 641
  Gaur D, Galbraith L, Wilkinson SG "Structural characterisation of a rhamnan and a fucorhamnan, both present in the lipopolysaccharide of Burkholderia vietnamiensis strain LMG 10926" - European Journal of Biochemistry 258(2) (1998) 696-701
  

  The polymeric fraction isolated after mild acid hydrolysis of the lipopolysaccharide (LPS) from Burkholderia vietnamiensis strain LMG 10926 contained L-rhamnose (Rha) and D-fucose (Fuc). From NMR studies supported by the results of methylation analysis and Smith degradation, it could be inferred that the material was probably a mixture of two glycans. One component was a linear rhamnan with a trisaccharide repeating unit (1); the other was a branched fucorhamnan with a tetrasaccharide repeating unit (2). The presence of two distinct polymeric fractions in LPS is a common feature for Burkholderia species. [structures: see text]

  Lipopolysaccharide, strain, structural, Burkholderia, Burkholderia vietnamiensis, fucorhamnan, rhamnan

  NCBI PubMed ID: 9874236
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: S.G.Wilkinson@chem.hull.ac.uk
  Institutions: Department of Chemistry, University of Hull, England.
  Methods: methylation, NMR, Smith degradation
  
   
  
  Burkholderia vietnamiensis LMG 10926
  CSDB ID 411 (all data & tools)
• 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_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Burkholderia vietnamiensis LMG 10926
  CSDB ID 27884 (all data & tools)
• Article ID: 4637
  Wang L, Vinogradov EV, Bogdanove AJ "Requirement of the lipopolysaccharide O-chain biosynthesis gene wxocB for type III secretion and virulence of Xanthomonas oryzae pv. oryzicola" - Journal of Bacteriology 195(9) (2013) 1959-1969
  

  Xanthomonas oryzae pv. oryzicola causes bacterial leaf streak of rice. A mutant disrupted in wxocB, predicted to encode an enzyme for lipopolysaccharide (LPS) synthesis, was previously shown to suffer reduced virulence. Here, we confirm a role for wxocB in virulence and demonstrate its requirement for LPS O-chain assembly. Structure analysis indicated that wildtype LPS contains a poly-rhamnose O-chain with irregular, variant residues and a core oligosaccharide identical to that of other Xanthomonas spp., and that the wxocB mutant lacks the O-chain. The mutant also showed moderate impairment in exopolysaccharide (EPS) production, but comparison with an EPS-deficient mutant demonstrated that this impairment could not account entirely for the reduced virulence. The wxocB mutant was not detectably different from wildtype in its induction of pathogenesis-related rice genes, type II secretion competence, flagellar motility, or resistance to two phytoalexins or resveratrol, and it was more, not less resistant to oxidative stress and a third phytoalexin, indicating that none of these properties is involved. The mutant was more sensitive to SDS and to Novobiocin, so increased sensitivity to some host-derived antimicrobials cannot be ruled out. However, the mutant showed a marked decrease in type III secretion into plant cells. This was not associated with any change in expression of genes for type III secretion, or the ability to attach to plant cells in suspension. Thus, virulence of the wxocB mutant is likely reduced primarily due to a direct, possibly structural, effect of the loss of the O-chain on type III delivery of effector proteins.

  Lipopolysaccharide, biosynthesis, structure, core oligosaccharide, mutant, exopolysaccharide, O-chain, motility, Oxiidative stress, Xanthomonas oryzae, wxocB

  NCBI PubMed ID: 23435979
  Publication DOI: 10.1128/JB.02299-12
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: Adam J. Bogdanove
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada, Department of Plant Pathology, Iowa State University, Ames, IA 50011
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, PCR, GC-MS, ESI-MS, mild acid hydrolysis, Smith degradation, genetic methods, binding assays
  
   
  
  Xanthomonas oryzae pv. oryzicola BLS303
  CSDB ID 29383 (all data & tools)
• Article ID: 4952
  De Felice A, Di Lorenzo F, Scherlach K, Ross C, Silipo A, Hertweck C, Molinaro A "Structural investigation of the lipopolysaccharide O-chain isolated from Burkholderia fungorum strain DSM 17061" - Carbohydrate Research 433 (2016) 31-35
  

  Gram-negative bacteria exhibit lipopolysaccharides (LPSs) on their outer membrane surface. LPS is considered one of the most potent bacterial virulence factors. Here we report the elucidation of the LPS O-chain structure isolated from Burkholderia fungorum, a bacterium isolated from the white-rot fungus Phanerochaete chrysosporium that can act as a pathogen for plants and domesticated animals. The structure was determined by the employment of detailed chemical and NMR spectroscopy analyses as the following.

  NMR spectroscopy, O-chain, outer membrane, lipopolysaccharide (LPS), Structural characterization, Burkholderia fungorum

  NCBI PubMed ID: 27434832
  Publication DOI: 10.1016/j.carres.2016.07.008
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: silipo@unina.it
  Institutions: Leibniz Institute for Natural Product Research and Infection Biology, Hans Knoll Institute (HKI), Jena, Germany, Friedrich Schiller University, Jena, Germany, Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126, Naples, Italy
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, NMR-1D, reduction with NaBD4, acetylation
  
   
  
  Burkholderia fungorum DSM 17061
  CSDB ID 11797 (all data & tools)
• Article ID: 4992
  Di Lorenzo F, Silipo A, Andersen Gersby LB, Palmigiano A, Lanzetta R, Garozzo D, Boyer C, Pruvost O, Newman MA, Molinaro A "Xanthomonas citri pv. citri Pathotypes: LPS Structure and Function as Microbe-Associated Molecular Patterns" - Chembiochem: a European Journal of Chemical Biology 18(8) (2017) 772-781
  

  Xanthomonas citri pv. citri is the pathogen responsible for Asiatic citrus canker, one of the most serious citrus diseases worldwide. The lipopolysaccharide (LPS) molecule has been demonstrated to be involved in X. citri pv. citri virulence. Despite enormous progress in investigations of the molecular mechanisms for bacterial pathogenicity, determination of the detailed LPS structure-activity relationship is limited, as the current knowledge is mainly based on structural determination of one X. citri pv. citri strain. As X. citri pv. citri strains are distinguished into three main pathogenicity groups, we characterized the full structure of the LPS from two pathotypes that differ in their host-range specificity. This revealed an intriguing difference in LPS O-chain structure. We also tested the LPSs and isolated lipid A moieties for their ability to act as microbe-associated molecular patterns in Arabidopsis thaliana. Both LPS/lipid As induced ROS accumulation, but no difference was observed between the two pathotypes.

  antigens, structure elucidation, lipopolysaccharide (LPS), innate immunity, reactive oxygen species (ROS), Xanthomonas citri pv.citri

  NCBI PubMed ID: 28186388
  Publication DOI: 10.1002/cbic.201600671
  Journal NLM ID: 100937360
  Publisher: Weinheim, Germany: Wiley Interscience
  Correspondence: silipo@unina.it
  Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126, Naples, Italy, CNR-Istituto per i Polimeri, Compositi e Biomateriali IPCB, via Gaifami 18, 95126, Catania, Italy, CIRAD, UMR Peuplements Vegetaux et Bioagresseurs en Milieu Tropical (PVBMT), Saint Pierre, La Reunion, France, Department of Plant and Environmental Sciences, University of Copenhagen, 1871, Frederiksberg, Copenhagen, Denmark
  Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, acid hydrolysis, MALDI-TOF MS, biological assays, composition analysis, methanolysis, alkaline hydrolysis, reduction with NaBD4, acetylation, gel-filtration
  
   
  
  Xanthomonas citri pv. citri NCPPB 3562
  CSDB ID 11889 (all data & tools)
• Article ID: 5143
  Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" - Natural Product Reports 35(12) (2018) 1251-1293
  

  Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.

  lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism

  Publication DOI: 10.1039/C8NP00046H
  Journal NLM ID: 8502408
  Publisher: London: Royal Society of Chemistry
  Correspondence: charles.gauthier@iaf.inrs.ca
  Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
  
   
  
  Burkholderia vietnamiensis LMG 10926
  CSDB ID 12512 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 4952
  De Felice A, Di Lorenzo F, Scherlach K, Ross C, Silipo A, Hertweck C, Molinaro A "Structural investigation of the lipopolysaccharide O-chain isolated from Burkholderia fungorum strain DSM 17061" - Carbohydrate Research 433 (2016) 31-35
  

  Gram-negative bacteria exhibit lipopolysaccharides (LPSs) on their outer membrane surface. LPS is considered one of the most potent bacterial virulence factors. Here we report the elucidation of the LPS O-chain structure isolated from Burkholderia fungorum, a bacterium isolated from the white-rot fungus Phanerochaete chrysosporium that can act as a pathogen for plants and domesticated animals. The structure was determined by the employment of detailed chemical and NMR spectroscopy analyses as the following.

  NMR spectroscopy, O-chain, outer membrane, lipopolysaccharide (LPS), Structural characterization, Burkholderia fungorum

  NCBI PubMed ID: 27434832
  Publication DOI: 10.1016/j.carres.2016.07.008
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: silipo@unina.it
  Institutions: Leibniz Institute for Natural Product Research and Infection Biology, Hans Knoll Institute (HKI), Jena, Germany, Friedrich Schiller University, Jena, Germany, Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126, Naples, Italy
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, NMR-1D, reduction with NaBD4, acetylation
  
   
  
  Burkholderia fungorum DSM 17061
  CSDB ID 11369 (all data & tools)
• Article ID: 4992
  Di Lorenzo F, Silipo A, Andersen Gersby LB, Palmigiano A, Lanzetta R, Garozzo D, Boyer C, Pruvost O, Newman MA, Molinaro A "Xanthomonas citri pv. citri Pathotypes: LPS Structure and Function as Microbe-Associated Molecular Patterns" - Chembiochem: a European Journal of Chemical Biology 18(8) (2017) 772-781
  

  Xanthomonas citri pv. citri is the pathogen responsible for Asiatic citrus canker, one of the most serious citrus diseases worldwide. The lipopolysaccharide (LPS) molecule has been demonstrated to be involved in X. citri pv. citri virulence. Despite enormous progress in investigations of the molecular mechanisms for bacterial pathogenicity, determination of the detailed LPS structure-activity relationship is limited, as the current knowledge is mainly based on structural determination of one X. citri pv. citri strain. As X. citri pv. citri strains are distinguished into three main pathogenicity groups, we characterized the full structure of the LPS from two pathotypes that differ in their host-range specificity. This revealed an intriguing difference in LPS O-chain structure. We also tested the LPSs and isolated lipid A moieties for their ability to act as microbe-associated molecular patterns in Arabidopsis thaliana. Both LPS/lipid As induced ROS accumulation, but no difference was observed between the two pathotypes.

  antigens, structure elucidation, lipopolysaccharide (LPS), innate immunity, reactive oxygen species (ROS), Xanthomonas citri pv.citri

  NCBI PubMed ID: 28186388
  Publication DOI: 10.1002/cbic.201600671
  Journal NLM ID: 100937360
  Publisher: Weinheim, Germany: Wiley Interscience
  Correspondence: silipo@unina.it
  Institutions: Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126, Naples, Italy, CNR-Istituto per i Polimeri, Compositi e Biomateriali IPCB, via Gaifami 18, 95126, Catania, Italy, CIRAD, UMR Peuplements Vegetaux et Bioagresseurs en Milieu Tropical (PVBMT), Saint Pierre, La Reunion, France, Department of Plant and Environmental Sciences, University of Copenhagen, 1871, Frederiksberg, Copenhagen, Denmark
  Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, acid hydrolysis, MALDI-TOF MS, biological assays, composition analysis, methanolysis, alkaline hydrolysis, reduction with NaBD4, acetylation, gel-filtration
  
   
  
  Xanthomonas citri pv. citri CFBP 2911
  CSDB ID 12077 (all data & tools)
• Article ID: 5143
  Cloutier M, Muru K, Ravicoularamin G, Gauthier C "Polysaccharides from Burkholderia species as targets for vaccine development, immunomodulation and chemical synthesis" - Natural Product Reports 35(12) (2018) 1251-1293
  

  Burkholderia species are a vast group of human pathogenic, phytopathogenic, and plant- or environment-associated bacteria. B. pseudomallei, B. mallei, and B. cepacia complex are the causative agents of melioidosis, glanders, and cystic fibrosis-related infections, respectively, which are fatal diseases in humans and animals. Due to their high resistance to antibiotics, high mortality rates, and increased infectivity via the respiratory tract, B. pseudomallei and B. mallei have been listed as potential bioterrorism agents by the Centers for Disease Control and Prevention. Burkholderia species are able to produce a large network of surface-exposed polysaccharides, i.e., lipopolysaccharides, capsular polysaccharides, and exopolysaccharides, which are virulence factors, immunomodulators, major biofilm components, and protective antigens, and have crucial implications in the pathogenicity of Burkholderia-associated diseases. This review provides a comprehensive and up-to-date account regarding the structural elucidation and biological activities of surface polysaccharides produced by Burkholderia species. The chemical synthesis of oligosaccharides mimicking Burkholderia polysaccharides is described in detail. Emphasis is placed on the recent research efforts toward the development of glycoconjugate vaccines against melioidosis and glanders based on synthetic or native Burkholderia oligo/polysaccharides.

  lipopolysaccharides, Burkholderia, capsular polysaccharides, Oligosaccharides, glycoconjugate vaccines, antigens, exopolysaccharides, surface polysaccharide, virulence factor, Biofilm, chemical synthesis, bioterrorism

  Publication DOI: 10.1039/C8NP00046H
  Journal NLM ID: 8502408
  Publisher: London: Royal Society of Chemistry
  Correspondence: charles.gauthier@iaf.inrs.ca
  Institutions: INRS-Institut Armand-Frappier, Universite du Quebec, 531, boul. des Prairies, Laval, Canada
  
   
  
  Burkholderia fungorum DSM 17061
  CSDB ID 12527 (all data & tools)