Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: O-antigen A-band
Compound class: O-polysaccharide, K-antigen, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823

• Article ID: 1314
  Zdorovenko EL, Zatonsky GV, Zdorovenko GM, Pasichnik LA, Shashkov AS, Knirel YA "Structural heterogeneity in the lipopolysaccharides of Pseudomonas syringae with O-polysaccharide chains having different repeating units" - Carbohydrate Research 336(4) (2001) 329-336
  

  Studies by sugar and methylation analyses, Smith degradation, and 1H and 13C NMR spectroscopy revealed a structural heterogeneity in the O-polysaccharides of Pseudomonas syringae pvs. coronafaciens IMV 9030 and atrofaciens IMV 8281 owing to the presence of different types of repeating units. In strain IMV 9030, the major repeating units are a linear α-L-rhamnose trisaccharide and a tetrasaccharide (A, n=0 or 1). A minor repeating unit is a branched pentasaccharide with an α-L-rhamnose main chain and a lateral 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc) residue (B, X=2, n=1). In strain IMV 8281, all repeating units are branched and differ in size and position of substitution of one of the α-L-rhamnose residues (tetrasaccharide, B, X=3, n=0; pentasaccharides, B, X=2 or 3, n=1). [structure--see text] Reinvestigation of the structure of the branched O-polysaccharide of P. syringae pv. tomato IPGR 140 showed that, together with the major tetrasaccharide repeating unit (B, X=3, n=0) [Knirel, Y. A., et al. Carbohydr. Res. 1993, 243, 199-204], it has a minor pentasaccharide repeating unit (B, X=3, n=1)

  Lipopolysaccharide, O-antigen, Bacterial polysaccharide, Pseudomonas syringae, phytopathogen, structural heterogeneity

  NCBI PubMed ID: 11728403
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, Moscow, Russia, Zablotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukra, Zablotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine
  Methods: NMR-2D, methylation, NMR, Smith degradation
  
   
  
  Pseudomonas syringae pv. coronafaciens IMV9030
  CSDB ID 5955 (all data & tools)
• Article ID: 1339
  Zubkov VA, Nazarenko EL, Ivanova EP, Gorshkova NM, Gorshkova RP "Structure of the repeating unit of the O-specific polysaccharide of Marinomonas communis strain ATCC27118(T)" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 25(4) (1999) 290-292
  

  O-specific polysaccharide was isolated from the bacteria Marinomonas communis strain ATCC27118(T) and studied by NMR spectroscopy and chemical methods. As a result following structure of the repeating unit was determined [see text]

  structure, strain, polysaccharide, repeating unit, O-specific, O-specific polysaccharide, Marinomonas

  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Correspondence: elnaz@piboc.marine.su
  Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok
  Methods: NMR-2D, methylation, NMR
  
   
  
  Marinomonas communis ATCC 27118 (T)
  CSDB ID 5993 (all data & tools)
• Article ID: 1642
  Reuhs BL, Relic B, Forsberg LS, Marie C, Ojanen-Reuhs T, Stephens SB, Wong CH, Jabbouri S, Broughtjn WL "Structural characterization of a flavonoid-inducible Pseudomonas aeruginosa A-band-like O antigen of Rhizobium sp. strain NGR234, required for the formation of nitrogen-fixing nodules" - Journal of Bacteriology 187(18) (2005) 6479-6487
  

  Rhizobium (Sinorhizobium) sp. strain NGR234 contains three replicons, the smallest of which (pNGR234a) carries most symbiotic genes, including those required for nodulation and lipo-chito-oligosaccharide (Nod factor) biosynthesis. Activation of nod gene expression depends on plant-derived flavonoids, NodD transcriptional activators, and nod box promoter elements. Nod boxes NB6 and NB7 delimit six different types of genes, one of which (fixF) is essential for the formation of effective nodules on Vigna unguiculata. In vegetative culture, wild-type NGR234 produces a distinct, flavonoid-inducible lipopolysaccharide (LPS) that is not produced by the mutant (NGRomegafixF); this LPS is also found in nitrogen-fixing bacteroids isolated from V. unguiculata infected with NGR234. Electron microscopy showed that peribacteroid membrane formation is perturbed in nodule cells infected by the fixF mutant. LPSs were purified from free-living NGR234 cultured in the presence of apigenin. Structural analyses showed that the polysaccharide portions of these LPSs are specialized, rhamnose-containing O antigens attached to a modified core-lipid A carrier. The primary sequence of the O antigen is [-3)-α-L-Rhap-(1,3)-α-L-Rhap-(1,2)-α-L-Rhap-(1-]n, and the LPS core region lacks the acidic sugars commonly associated with the antigenic outer core of LPS from noninduced cells. This rhamnan O antigen, which is absent from noninduced cells, has the same primary sequence as the A-band O antigen of Pseudomonas aeruginosa, except that it is composed of L-rhamnose rather than the D-rhamnose characteristic of the latter. It is noteworthy that A-band LPS is selectively maintained on the P. aeruginosa cell surface during chronic cystic fibrosis lung infection, where it is associated with an increased duration of infection.

  antigen, strain, structural, characterization, O-antigen, O antigen, Pseudomonas, Pseudomonas aeruginosa, Rhizobia, Rhizobium, formation, nitrogen fixing, nodule

  NCBI PubMed ID: 16159781
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: william.broughton@bioveg.unige.ch
  Institutions: Whistler Center for Carbohydrate Research, Department of Food Science, Purdue University, 1160 Food Science Building, West Lafayette, Indiana 47907-11601, LBMPS, Universite de Geneve, 30 quai Ernest-Ansermet, 1211 Geneve 4, Switzerland, Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Rd., Athens, GA, USA3, Pusat Penyelidikan Sains Kajihayat, Universiti Sains Malaysia, Pulau Pinang, Malaysia
  Methods: NMR
  
   
  
  Rhizobium sp. NGR234
  CSDB ID 10609 (all data & tools)
• Article ID: 2108
  Dengler T, Himmelspach K, Jann B, Jann K "Structure of the capsular K3 antigen of Escherichia coli O4:K3:H4, a polysaccharide containing a 4-deoxy-2-hexulosonic acid" - Carbohydrate Research 178 (1988) 191-201
  
  Journal NLM ID: 0043535
  Publisher: Elsevier
  
   
  
  Escherichia coli K3
  CSDB ID 115395 (all data & tools)
• Article ID: 3743
  Molinaro A, Newman M, Lanzetta R, Parrilli M "The structures of lipopolysaccharides from plant-associated Gram-negative bacteria" - European Journal of Organic Chemistry 2009(34) (2009) 5887-5896
  

  Gram-negative bacterial lipopolysaccharides (LPSs) have multiple roles in plant-microbe interactions. LPSs contribute to the low permeabilities of bacterial outer membranes, which act as barriers to protect bacteria from plant-derived antimicrobial substances. Conversely, perception of LPSs by plant cells can lead to the triggering of defence responses or to the priming of the plant to respond more rapidly and/or to a greater degree to subsequent pathogen challenge. LPSs are thus key molecules in the interactions between bacteria and plants, either in symbiosis or pathogenesis. Since LPSs are glycoconjugates genetically and chemically consisting of three different molecular regions, their detailed structure elucidation is a very topical and major scientific task for chemists, and is achieved by a combination of state-of-art chemical and spectroscopic techniques. Knowledge of LPSs' chemical structures is an important prerequisite for any further understanding of the biological processes in plant-microbe interactions. Moreover, the LPSs from Gram-negative bacteria - especially those originating from plant-associated bacteria - are a great source of novel monosaccharides with unusual and occasionally astounding chemical structures, never found in the eukaryotic world. This review presents the structures of LPSs from plant-associated bacteria isolated and identified from 2001 onwards.

  lipopolysaccharides, structure elucidation, glycolipids, innate immunity, immunochemistry, plant-associated bacteria

  Publication DOI: 10.1002/ejoc.200900682
  Journal NLM ID: 9805750
  Publisher: Wiley-VCH
  Correspondence: molinaro@unina.it
  Institutions: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, via Cinthia 4, 80126 Napoli, Italy, Fax: +39-081-674393, Faculty of Life Sciences, Department of Plant Biology & Biotechnology, University of Copenhagen, 1871 Frederiksberg, Denmark
  
   
  
  Pseudomonas syringae pv. coronafaciens IMV 9030
  CSDB ID 24108 (all data & tools)
• Article ID: 3968
  Zdorovenko GM, Zdorovenko EL "Pseudomonas syringae lipopolysaccharides: Immunochemical characteristics and structure as a basis for strain classification" - Mikrobiologiia = Microbiology [Russian] 79(1) (2010) 47-57
  

  Lipopolysaccharide (LPS) preparations of 34 Pseudomonas syringae strains of 19 pathovars were prepared by saline extraction from wet cells and purified by repeated ultracentrifugation. The preparations reacted with homologous O-antisera, obtained by rabbit immunization with heat-killed bacterial cells. Through inhibition of homologous reactions between LPS preparations of heterologous strains (enzyme immunoassay, EIA), it was established for the first time that high serological affinity between strains is observed only if their LPS contains O-specific polysaccharide chains (OPS) comprised of completely identical rather than partially similar units. The central linear part of the OPS was found to be serologically inert when shielded with side groups. Data on immunochemical characteristics of the LPS and OPS structure are analyzed in relation to the design of P. syringae classification scheme.

  Lipopolysaccharide, structure, O-specific polysaccharide, Pseudomonas syringae, classification, immunochemistry

  NCBI PubMed ID: 20411661
  Publication DOI: 10.1134/S0026261710010078
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: evelina@ioc.ac.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kyiv, 03143 Ukraine
  Methods: partial acid hydrolysis, EIA, serological methods, de-N-acetylation/deamination
  
   
  
  Pseudomonas syringae pv. coronafaciens IMV 9030
  CSDB ID 25898 (all data & tools)
• 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_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
  
   
  
  Marinomonas communis
  CSDB ID 27833 (all data & tools)
• Article ID: 4441
  Bedini E, Carabellese A, Comegna D, De Castro C, Parrilli M "Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria" - Tetrahedron 62(36) (2006) 8474-8483
  

  The synthesis of the tetrasaccharide rhamnanic motif a-l-Rha-(1-3)-a-l-Rha-(1-2)-a-l-Rha-(1-2)-a-l-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl trifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups.

  Lipopolysaccharide, oligosaccharide, rhamnose, glycosylation, Phytopathogenic bacteria

  Publication DOI: 10.1016/j.tet.2006.06.084
  Journal NLM ID: 2984170R
  Publisher: Pergamon Press
  Correspondence: ebedini@unina.it
  Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli 'Federico II', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical methods
  
   
  
  Pseudomonas
  CSDB ID 29000 (all data & tools)
• Article ID: 5177
  Laguri C, Silipo A, Martorana AM, Schanda P, Marchetti R, Polissi A, Molinaro A, Simorre JP "Solid State NMR Studies of Intact Lipopolysaccharide Endotoxin" - ACS Chemical Biology 13(8) (2018) 2106-2113
  

  Lipopolysaccharides (LPS) are complex glycolipids forming the outside layer of Gram-negative bacteria. Their hydrophobic and heterogeneous nature greatly hampers their structural study in an environment similar to the bacterial surface. We have studied LPS purified from E. coli and pathogenic P. aeruginosa with long O-antigen polysaccharides assembled in solution as vesicles or elongated micelles. Solid-state NMR with magic-angle spinning permitted the identification of NMR signals arising from regions with different flexibilities in the LPS, from the lipid components to the O-antigen polysaccharides. Atomic scale data on the LPS enabled the study of the interaction of gentamicin antibiotic bound to P. aeruginosa LPS, for which we could confirm that a specific oligosaccharide is involved in the antibiotic binding. The possibility to study LPS alone and bound to a ligand when it is assembled in membrane-like structures opens great prospects for the investigation of proteins and antibiotics that specifically target such an important molecule at the surface of Gram-negative bacteria.

  NMR, LPS, O-antigen, identification, solid state, endotoxin, structural studies, glycolipid

  NCBI PubMed ID: 29965728
  Publication DOI: 10.1021/acschembio.8b00271
  Journal NLM ID: 101282906
  Publisher: Washington, DC: American Chemical Society
  Correspondence: molinaro@unina.it; jean-pierre.simorre@ibs.fr
  Institutions: Universite Grenoble Alpes, CNRS, CEA, IBS, F-38000 Grenoble, France, University of Naples Federico II, Department of Chemical Sciences, via cintia 4, Napoli, Italy, University of Milano, Department of Pharmacological and Biomolecular Sciences, Via Balzaretti 9, Milano, Italy
  Methods: STD NMR, MAS STD NMR
  
   
  
  Pseudomonas aeruginosa PAO1
  CSDB ID 12650 (all data & tools)