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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_1394181

• Article ID: 3452
  Cimmino A, Marchi G, Surico G, Hanuszkiewicz A, Evidente A, Holst O "The structure of the O-specific polysaccharide of the lipopolysaccharide from Pantoea agglomerans strain FL1" - Carbohydrate Research 343(2) (2008) 392-396
  

  A neutral O-specific polysaccharide consisting of d-rhamnose was obtained by mild acid hydrolysis of the lipopolysaccharide of the plant pathogenic bacterium Pantoea agglomerans strain FL1, a common epiphyte of many plant species, and associated with Pseudomonas savastanoi pv. savastanoi in young and apparently intact olive knots. By means of compositional and methylation analyses, and NMR spectroscopy, the chemical repeating unit of the polymer was identified as a linear tetrasaccharide of the structure: [structure: see text].

  Lipopolysaccharide, NMR spectroscopy, O-specific polysaccharide, Pantoea agglomerans, Olive knot

  NCBI PubMed ID: 18039532
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: oholst@fz-borstel.de
  Institutions: Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, D-23845 Borstel, Germany, Dipartimento di Scienze del Suolo, della Pianta, dell' Ambiente e delle Produzioni Animali, Universita Degli Studi di Napoli Federico II, I-80055 Portici (NA), Italy
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, GLC, mild acid hydrolysis, composition analysis, NMR-1D
  
   
  
  Pantoea agglomerans FL1
  CSDB ID 22625 (all data & tools)
• Article ID: 3744
  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
  
   
  
  Pantoea agglomerans FL1
  CSDB ID 24121 (all data & tools)
• Article ID: 3822
  Boiko AS, Smol'kina ON, Fedonenko YP, Zdorovenko EL, Kachala VV, Konnova SA, Ignatov VV "O-polysaccharide structure in serogroup I Azospirilla" - Mikrobiologiia = Microbiology [Russian] 79(2) (2010) 197-205
  

  Lipopolysaccharides (LPS) and O-specific polysaccharides (OPS) were obtained from the outermembrane of four Azospirillum strains previously assigned to serogroup I based on the serological affinityrevealed by the antibodies (AB) to the LPS of A. brasilense Sp245. Investigation, including determination ofmonosaccharide composition, methylation analysis, and one- and two-dimensional NMR spectroscopy, wascarried out to determine the OPS structure. The OPSs of A. brasilense Sp107 and S27 and of A. lipoferumRG20a were found to have an identical structure of repeating units represented by a linear penta-D-rhamnan,as was previously described for the OPSs of A. brasilense Sp245 and SR75. The OPS of A. brasilense SR15was found to consist of tetrasaccharide repeating units of the following structure: frame0 2)--D-Rhap-(1 frame1 2)--D-Rhap-(1 frame2 3)--D-Rhap-(1 frame3 2)--D-Rhap-(1 frame4. An opine compound, N-(1-carboxyethyl)-orni-thine, closely associated with the LPS of A. brasilense SR15, was identified in azospirilla for the first time. Thepresence of a 6-deoxisugar (D-rhamnose) in the OPS structure was shown to be the chemical basis of the sero-logical similarity and the reason for classification of these strains within the serogroup I.

  Lipopolysaccharide, serological characterization, Azospirillum, structure of O-specific polysaccharides

  Publication DOI: 10.1134/S0026261710020116
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: alevtinab10@mail.ru
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Saratov, Russia
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, SDS-PAGE, EIA, Smith degradation, composition analysis, NMR-1D, serological methods
  
   
  
  Azospirillum brasilense I SR15
  CSDB ID 25542 (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
  
   
  
  Pantoea agglomerans FL1, Azospirillum brasilense SR15
  CSDB ID 27577 (all data & tools)
• Article ID: 4999
  Hashimoto M, Satou R, Ozono M, Inagawa H, Soma GI "Characterization of the O-antigen polysaccharide derived from Pantoea agglomerans IG1 lipopolysaccharide" - Carbohydrate Research 449 (2017) 32-36
  

  A polysaccharide fraction was isolated from the Pantoea agglomerans IG1 lipopolysaccharide (IP-PA1), and its O-antigenic polysaccharide was characterized by chemical analyses and 1D and 2D 1H and 13C NMR spectroscopy. The polysaccharide is composed of linear tetrasaccharide repeating units, consisting of glucose and rhamnose, where 40% of one of the rhamnose residues is substituted with glucose: →2)-α-l-Rhap-(1→6)-α-d-Glcp-(1→2)-[β-d-Glcp-(1→3)]0.4-α-l-Rhap-(1→2)-α-l-Rhap-(1→.

  Lipopolysaccharide, O-antigenic polysaccharide, NMR spectroscopy, Pantoea agglomerans, Wheat symbiotic bacteria

  NCBI PubMed ID: 28686930
  Publication DOI: 10.1016/j.carres.2017.06.017
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: hassy@eng.kagoshima-u.ac.jp
  Institutions: Department of Chemistry, Biotechnology, and Chemical Engineering, Kagoshima University, Kagoshima, Japan, Faculty of Medicine, Kagawa University, Miki-cho, Kita-gun, Kagawa, Japan, Research Institute for Healthy Living, Niigata University of Pharmacy and Applied Life Sciences, Akiba-ku, Niigata, Japan, Control of Innate Immunity TRA, Bio-Lab, Kagawa, Japan
  Methods: 13C NMR, 1H NMR, methylation, gel filtration, GC-MS, sugar analysis, dephosphorylation, 31P NMR, acid hydrolysis
  
   
  
  Pantoea agglomerans FL1
  CSDB ID 12104 (all data & tools)
• Article ID: 5059
  Zdorovenko EL, Kadykova AA, Shashkov AS, Varbanets LD, Bulyhina TV, Knirel YA "Lipopolysaccharide of Pantoea agglomerans 7969: Chemical identification, function and biological activity" - Carbohydrate Polymers 165 (2017) 351-358
  

  Lipopolysaccharide (LPS) of Pantoea agglomerans 7969 isolated from apple tree was purified and characterized chemically by sugar and fatty acid analysis. Lipid A was analysed by negative-ion mode ESI MS and found to consist mainly of hexa- and tetra-acyl species typical of E. coli lipid A. The O-specific polysaccharide of the LPS was studied by sugar analysis, Smith degradation, and one- and two-dimensional 1H and 13C NMR spectroscopy. The polysaccharide is built up of linear tetrasaccharide repeating units, and about ∼25% repeats contain glycerol 1-phosphate on the GlcNAc residue: →3)-α-l-Rhap-(1→6)-α-d-Manp-(1→3)-α-d-Fucp-(1→3)-β-d-GlcpNAc-(1→ ~25% Gro-1-P-(O→6). The LPS showed low levels of toxic and pyrogenic activities and reduced the average adhesion and the index of adhesiveness.

  lipid A, O-specific polysaccharide, Pantoea agglomerans, toxicity, O-Polysaccharide structure, glycerol phosphate, Adhesiveness, Pyrogenicity

  NCBI PubMed ID: 28363559
  Publication DOI: 10.1016/j.carbpol.2017.02.053
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Correspondence: zdorovenko@mail.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, D.K. Zabolotny Insitute of Microbiology and Virology of the National Academy of Sciences, 154 Zabolotnoho Str., 03143 Kiev, Ukraine
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, dephosphorylation, 31P NMR, ESI-MS, GLC, Smith degradation, serological methods, GPC, acetylation, mild acid degradation, toxicity assays, pyrogenicity assays
  
   
  
  Pantoea agglomerans FL1
  CSDB ID 12330 (all data & tools)
• Article ID: 6139
  Shashkov AS, Tul'skaya EM, Potekhina NV, Dmitrenok AS, Senchenkova SN, Zaychikov VA, Dorofeeva LV, Evtushenko LI "D-Rhamnan and Pyruvate-Containing Teichuronic Acid from the Cell Wall of Rathayibacter sp. VKM Ac-2759" - Biochemistry (Moscow) 86(4) (2021) 506-516
  

  Rathayibacter sp. VKM Ac-2759 (family Microbacteriaceae, class Actinobacteria) contains two glycopolymers in the cell wall. The main chain of rhamnan, glycopolymer 1, is built from the repeating tetrasaccharide units carrying terminal arabinofuranose residues at the non-reducing end, →3)-α-[α-D-Araf-(1→2)]-D-Rhap-(1→2)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→. Similar to other described Rathayibacter species, rhamnose in the neutral glycopolymer of the VKM Ac-2759 strain is present in the D-configuration. Acetalated with pyruvic acid teichuronic acid, glycopolymer 2, is composed of the repeating tetrasaccharide units, →4)-β-D-GlcpA-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→3)-β-[4,6-S-Pyr]-D-Manp-(1→. Glycopolymers 1 and 2 were identified in prokaryotic microorganisms for the first time and their structures were established by chemical analysis and NMR spectroscopy. The obtained data can be used in taxonomic research, as well as for elucidating the mechanisms of plant colonization and infection by bacteria of the Rathayibacter genus.

  cell wall, pyruvate, teichuronic acid, d-Rhamnan, glycopolymers, Rathayibacter

  NCBI PubMed ID: 33941071
  Publication DOI: 10.1134/S0006297921040118
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: em_tulskaya@mail.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia, All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Pushchino Scientific Center for Biological Research, Russian Academy of Sciences, Pushchino, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, anion-exchange chromatography, extraction, depyruvylation
  
   
  
  Pantoea agglomerans
  CSDB ID 9766 (all data & tools)