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Structure type: polymer chemical repeating unit
Trivial name: D-rhamnan
Compound class: CPS, O-polysaccharide
Contained glycoepitopes: IEDB_1394181,IEDB_145006,IEDB_145010

• Article ID: 72
  Fedonenko YP, Zatonsky GV, Konnova SA, Zdorovenko EL, Ignatov VV "Structure of the O-specific polysaccharide of the lipopolysaccharide of Azospirillum brasilense Sp245" - Carbohydrate Research 337(9) (2002) 869-872
  

  An O-specific polysaccharide was isolated from the lipopolysaccharide of a plant-growth-promoting bacterium Azospirillum brasilense Sp245 and studied by sugar analyses along with one- and two-dimensional 1H and 13C NMR spectroscopy, including NOESY. The polysaccharide was found to be a new rhamnan with a pentasaccharide repeating unit having the following structure: →2)-β-D-Rhap-(1→3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→2)-α-D-Rhap-(1→

  Lipopolysaccharide, O-antigen, Bacterial polysaccharide, Asymbiotic diazotroph, Azospirillum brasilense

  NCBI PubMed ID: 11996841
  Publication DOI: 10.1016/S0008-6215(02)00061-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Prospekt Entuziastov 13, 410015 Saratov, Russia, bN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Prospekt 47, Moscow, Russia
  Methods: methylation, NMR-2D, NMR, sugar analysis
  
   
  
  Azospirillum brasilense Sp245
  CSDB ID 2058 (all data & tools)
• Article ID: 1611
  Fedonenko YP, Borisov IV, Konnova ON, Zdorovenko EL, Katsy SA, Konnova SA, Ignatov VV "Determination of the structure of the repeated unit of the Azospirillum brasilense SR75 O-specific polysaccharide and homology of the lps loci in the plasmids of Azospirillum brasilense strains SR75 and Sp245" - Mikrobiologiia = Microbiology [Russian] 74(5) (2005) 626-632
  

  The structural identity of the repeated unit in O-specific polysaccharides (OPSs) present in the outer membrane of strain SR75 of the bacterium Azospirillum brasilense, isolated from wheat rhizosphere in Saratov oblast, and the OPSs of previously studied A. brasilense strain Sp245, isolated from surface-sterilized wheat roots in Brazil, has been demonstrated. Plasmid profiles, DNA restriction, and hybridization assays suggested that A. brasilense strains SR75 and Sp245 have different genomic structures. It was shown that homologous lps loci of both strains was localized in their plasmid DNA. This fact allows us to state that, despite their different origin, the development of the strains studied was convergent. Presumably, the habitation of these bacteria in similar ecological niches influenced this process in many respects

  LPS, structure, DNA, strain, structural, polysaccharide, determination, bacteria, O-specific, O-specific polysaccharide, Azospirillum brasilense, polysaccharides, plasmid, O-specific polysaccharides, homology, membrane, outer membrane, root, assay, origin, Plasmids, homologous, development, Azospirillum, P, profile, restriction, ecological, rhizosphere, wheat

  NCBI PubMed ID: 16315981
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Institutions: Institute of biochemistry and Physiology of Plants and Microorganisms RAS, Saratov
  Methods: methylation, NMR, sugar analysis
  
   
  
  Azospirillum brasilense Sp245, Azospirillum brasilense SR75
  CSDB ID 10534 (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
  
   
  
  Azospirillum brasilense SP245
  CSDB ID 24124 (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 Sp245
  CSDB ID 25187 (all data & tools)
• Article ID: 3844
  Fedonenko YP, Katsy EI, Petrova LP, Boyko AS, Zdorovenko EL, Kachala VV, Shashkov AS, Knirel YA "The structure of the O-specific polysaccharide from a mutant of nitrogen-fixing rhizobacterium Azospirillum brasilense Sp245 with an altered plasmid content" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 36(2) (2010) 219-223
  

  The rhizobacteria Azospirillum brasilense Sp245 produce immunochemically different lipopolysaccharides LPSI and LPSII, both containing identical pentasaccharides built from Drhamnose residues as the repeating units of Ospecific polysaccharides (OPS). In this study, we report the structure of the OPS from A. brasilense LPSI-LPSII- mutant Sp245.5, which spontaneously lost the p85 and p120 plasmids upon the formation of a new 300MDa megaplasmid after the longterm storage of the bacteria in a rich medium. The repeating unit of the OPS of A. brasilense Sp245.5 appeared to be a disaccharide consisting of residues of Nacetyl-D-galactosamine and Nacetyl-D-mannosaminuronic acid: (formula, see text).

  Azospirillum brasilense, O-Specific polysaccharide structure, plasmid rearrangements

  NCBI PubMed ID: 20531482
  Publication DOI: 10.1134/S1068162010020111
  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Correspondence: fedonenko@ibppm.sgu.ru
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, pr. Entuziastov 13, Saratov, 410049 Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, acid hydrolysis, composition analysis
  
   
  
  Azospirillum brasilense Sp245
  CSDB ID 25241 (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
  
   
  
  Azospirillum brasilense Sp245, Azospirillum brasilense S27, Azospirillum lipoferum RG20a
  CSDB ID 27857 (all data & tools)
• Article ID: 4724
  Sigida EN, Fedorova EE, Zdorovenko EL, Burygin GL, Konnova SA, Ignatov VV "Characterization of the lipopolysaccharides of serogroup II Azospirillum strains" - Mikrobiologiia = Microbiology [Russian] 83(4) (2014) 326-334
  

  Lipopolysaccharides of six Azospirillum brasilense strains (SR50, SR80, SR88, SR109, SR111, SR115) and A. lipoferum SR 42 isolated from the rhizosphere of cereal plants of Saratov oblast, Russia and referred to serogroup II by serological analysis were studied. In the lipid A fatty acid composition, the lipopolysaccharides under study were similar to those of other Azospirillum strains and were characterized by a predominance of 3-hydroxytetradecanoic, 3-hydroxyhexadecanoic, and octadecenoic acids. Monosaccharide analysis of the O-specific polysaccharides (including determination of the absolute configurations, methylation analysis, and one- and two-dimensional NMR spectroscopy) revealed the presence of two types of repeating units in varying ratios. A high degree of serological similarity between the strains under study was shown to result from the presence of repeating units with identical structure of their O antigens.

  lipopolysaccharides, Azospirillum, structure of the Ospecific polysaccharide, serological investigation

  Publication DOI: 10.1134/S0026261714040158
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: Sigida EN
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Saratov, Russia, Chernyshevsky Saratov State University, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, ELISA, GLC, mild acid hydrolysis, Western blotting, serological methods, GPC
  
   
  
  Azospirillum brasilense Sp245
  CSDB ID 30464 (all data & tools)
• Article ID: 4844
  Fedonenko YP, Sigida EN, Konnova SA, Ignatov VV "Structure and serology of O-antigens of nitrogen-fixing rhizobacteria of the genus Azospirillum" - Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 64(5) (2015) 1024-1031
  

  The review presents a discussion of the published data of 2002 to 2014 dealing with structural studies of O-specific polysaccharides, representatives of the Azospirillum diazotrophic rhizobacteria, summarizing the results of a series of authors? studies. Some general structures incorporated in O-specific polysaccharides responsible for classification of bacterial cultures into serogroups on the basis of immunochemical studies were characterized. The structures of O-specific polysaccharides of seven azospirillum strains identical to those of previously studied strains are presented in this review for the first time.

  lipopolysaccharides, O-specific polysaccharides, Structures, Azospirillum, O-antigenic determinants

  Publication DOI: 10.1007/s11172-015-0971-x
  Journal NLM ID: 100912060
  Publisher: New York: Consultants Bureau
  Correspondence: si_elena@mail.ru
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms Russian Academy of Sciences, 13 prosp. Entuziastov, 410049 Saratov, Russian Federation
  
   
  
  Azospirillum brasilense Sp245, Azospirillum brasilense SR75, Azospirillum brasilense S27, Azospirillum brasilense Sp107, Azospirillum lipoferum RG20a
  CSDB ID 11020 (all data & tools)
• Article ID: 5430
  Evstigneeva SS, Sigida EN, Fedonenko YP, Konnova SA, Ignatov VV "Structural Properties of Capsular and O-Specific Polysaccharides of Azospirillum brasilense SP245 under Varying Cultivation Conditions" - Mikrobiologiia = Microbiology [Russian] 85(6) (2016) 664-671
  

  Effect of the carbon source in the culture medium and of the growth phase on the composition and structure of the capsular polysaccharides (CPSs) and lipopolysaccharides (LPSs) of the bacterium Azospirillum brasilense Sp245 was studied. Growth with fructose resulted in an increased carbohydrate content in the CPSs, while long-term cultivation resulted in an increased content of phosphorus in both CPSs and LPSs. The LPSs produced on the medium with fructose (regardless of the cultivation duration) and the LPSs of the bacteria grown with sodium malate until the stationary phase were characterized by higher levels of unsaturated fatty acids than the LPSs of the bacteria grown with sodium malate to the late exponential phase. The structures of the polysaccharides from the isolated glycopolymers were established using monosaccharide analysis, including determination of the absolute configurations and 1D and 2D NMR spectroscopy. This study is the first to report that the CPS of A. brasilense Sp245 grown with sodium malate to the end of the exponential phase is structurally identical to the O-polysaccharide from the LPS of this bacterium and that the LPS and CPS of A. brasilense Sp245 grown with fructose contain an additional homoglucan of the following structure: [→3)-α-D-Glcp-(1→]n.

  Lipopolysaccharide, capsular polysaccharide, Azospirillum brasilense, Azospirillum, cultivation conditions

  Publication DOI: 10.1134/S0026261716060096
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: Stels20295@yandex.ru
  Institutions: Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russia, Chernyshevskii National Research Saratov State University, Saratov, Russia
  Methods: 13C NMR, 1H NMR, GLC-MS, gel filtration, NMR-2D, SDS-PAGE, GLC, composition analysis
  
   
  
  Azospirillum brasilense SP245
  CSDB ID 1006 (all data & tools)
• 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/B978-0-12-819475-1.00005-5
  Publisher: 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
  
   
  
  Azospirillum brasilense SP245
  CSDB ID 6979 (all data & tools)