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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_225177,IEDB_241118,IEDB_885823,IEDB_983931,SB_192

• Article ID: 958
  MacLean LL, Perry MB "Structural studies on the O-polysaccharide of the lipopolysaccharide produced by Citrobacter rodentium (ATCC51459)" - European Journal of Biochemistry 268(22) (2001) 5740-5746
  

  Citrobacter rodentium is the etiologic agent of transmissible murine colonic hyperplasia (TMCH) and is the only Citrobacter species known to possess virulence factors homologous to human enteropathogenic and enterohemorrhagic Escherichia coli. Members of this species are considered clonal and represent the only known attaching and effacing bacterial pathogen of mice and thus provides a useful animal model for studying the molecular basis of attaching and effacing pathology. The lipopolysaccharide (LPS) produced by C. rodentium has not been previously studied or its possible role as a virulence factor determined. The structure of the LPS has been undertaken as a first step in an investigation of its possible role in pathogenesis. The structure of C. rodentium (ATCC51459, prototype TMCH isolate, original biotype 4280, previously designated DBS 100) LPS was determined from composition and methylation analyses, mass spectrometry, and two-dimensional nuclear magnetic resonance spectroscopy. The antigenic O-polysaccharide was found to be a high molecular mass branched polymer of repeating pentasaccharide units composed of 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), d-glucose (D-Glc), and L-rhamnose (L-Rha) in the molar ratio 2 : 2 : 1 linked through phosphate, and has the structure: [structure: see text]

  Lipopolysaccharide, strain, structural, O-polysaccharide, O polysaccharide, structural studies, Citrobacter

  NCBI PubMed ID: 11722558
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: malcolm.perry@nrc.ca
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6.
  Methods: NMR-2D, methylation, NMR, MS, composition analysis
  
   
  
  Citrobacter rodentium ATCC 51459
  CSDB ID 3192 (all data & tools)
• Article ID: 1467
  Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" - Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
  

  The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.

  Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity

  NCBI PubMed ID: 12546064
  Journal NLM ID: 0114365
  Publisher: Basel, Boston: Birkhaüser
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Citrobacter rodentium ATCC 51459
  CSDB ID 31913 (all data & tools)
• Article ID: 1547
  Olsson U, Lycknert K, Stenutz R, Weintraub A, Widmalm G "Structural analysis of the O-antigen polysaccharide from Escherichia coli O152" - Carbohydrate Research 340(1) (2005) 167-171
  

  The structure of the O-antigen polysaccharide (PS) from Escherichia coli O152 has been determined. Component analysis together with (1)H, (13)C and (31)P NMR spectroscopy were used to elucidate the structure. Inter-residue correlations were determined by (1)H,(31)P COSY, (1)H,(1)H NOESY and (1)H,(13)C heteronuclear multiple-bond correlation experiments. The PS is composed of pentasaccharide repeating units with the following structure: The structure is similar to that of the O-antigen polysaccharide from E. coli O173. The cross-reactivity between E. coli O152 and E. coli O3 may be explained by structural similarities in the branching region of their O-antigen polysaccharides

  NMR, structure, chemistry, correlation, structural, polysaccharide, O-antigen, repeating unit, analysis, polysaccharides, structural analysis, O antigen, Escherichia, Escherichia coli, NMR spectroscopy, region, spectroscopy, pentasaccharide, component, similarity, cross-reactivity, crossreactivity, organic, NOESY, COSY, heteronuclear

  NCBI PubMed ID: 15620681
  Publication DOI: 10.1016/j.carres.2004.11.008
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, F-82 Karolinska University Hospital, Huddinge Stockholm, Sweden
  Methods: NMR, composition analysis
  
   
  
  Escherichia coli O152
  CSDB ID 10116 (all data & tools)
• Article ID: 3196
  Stenutz R, Weintraub A, Widmalm G "The structures of Escherichia coli O-polysaccharide antigens" - FEMS Microbiology Reviews 30(3) (2006) 382-403
  

  Escherichia coli is usually a non-pathogenic member of the human colonic flora. However, certain strains have acquired virulence factors and may cause a variety of infections in humans and in animals. There are three clinical syndromes caused by E. coli: (i) sepsis/meningitis; (ii) urinary tract infection and (iii) diarrhoea. Furthermore the E. coli causing diarrhoea is divided into different 'pathotypes' depending on the type of disease, i.e. (i) enterotoxigenic; (ii) enteropathogenic; (iii) enteroinvasive; (iv) enterohaemorrhagic; (v) enteroaggregative and (vi) diffusely adherent. The serotyping of E. coli based on the somatic (O), flagellar (H) and capsular polysaccharide antigens (K) is used in epidemiology. The different antigens may be unique for a particular serogroup or antigenic determinants may be shared, resulting in cross-reactions with other serogroups of E. coli or even with other members of the family Enterobacteriacea. To establish the uniqueness of a particular serogroup or to identify the presence of common epitopes, a database of the structures of O-antigenic polysaccharides has been created. The E. coli database (ECODAB) contains structures, nuclear magnetic resonance chemical shifts and to some extent cross-reactivity relationships. All fields are searchable. A ranking is produced based on similarity, which facilitates rapid identification of strains that are difficult to serotype (if known) based on classical agglutinating methods. In addition, results pertinent to the biosynthesis of the repeating units of O-antigens are discussed. The ECODAB is accessible to the scientific community at http://www.casper.organ.su.se/ECODAB/

  NMR, structure, serotype, O-antigen, Enterobacteriacea, database

  NCBI PubMed ID: 16594963
  Publication DOI: 10.1111/j.1574-6976.2006.00016.x
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: andrej.weintraub@ki.se
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
  
   
  
  Escherichia coli O152
  CSDB ID 20689 (all data & tools)
• Article ID: 3364
  Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" - Carbohydrate Research 342(3-4) (2007) 297-344
  

  An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).

  synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters

  NCBI PubMed ID: 17092493
  Publication DOI: 10.1016/j.carres.2006.10.006
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: a.v.nikolaev@dundee.ac.uk
  Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
  
   
  
  Escherichia coli O152, Citrobacter rodentium ATCC 51459
  CSDB ID 21771 (all data & tools)
• Article ID: 3445
  Brockhausen I, Hu B, Liu B, Lau K, Szarek WA, Wang L, Feng L "Characterization of two b-1,3-glucosyltransferases from Escherichia coli serotypes O56 and O152" - Journal of Bacteriology 190(14) (2008) 4922-4932
  

  The O antigens of outer membrane-bound lipopolysaccharides (LPS) in Gram-negative bacteria are oligosaccharides consisting of repeating units with various structures and antigenicities. The O56 and O152 antigens of Escherichia coli both contain a Glc-β 1-3-GlcNAc linkage within the repeating unit. We have cloned and identified the genes (wfaP in O56 and wfgD in O152) within the two O antigen gene clusters that encode glucosyltransferases involved in the synthesis of this linkage. A synthetic substrate analog of the natural acceptor substrate undecaprenol-pyrophosphate-lipid (GlcNAc-PP-PhU) was used as an acceptor and UDP-Glc as a donor substrate to demonstrate that both wfgD and wfaP encode glucosyltransferases. Enzyme products from both glucosyltransferases were isolated by HPLC and analyzed by NMR. The spectra showed the expected Glc-β 1-3-GlcNAc linkage in the products, confirming that both WfaP and WfgD are UDP-Glc: GlcNAc-pyrophosphate-lipid β-1,3-glucosyltransferases. Both WfaP and WfgD have a DxD sequence which is proposed to interact with phosphate groups of the nucleotide donor through the coordination of a metal cation, and a short hydrophobic sequence at the C terminus that may help to associate the enzymes with the inner membrane. We showed that the enzymes have similar properties and substrate recognition. They both require divalent cation (Mn(2+) or Mg(2+)) for activity, are deactivated by detergents, have a broad pH optimum, and require the pyrophosphate-sugar linkage in the acceptor substrate for full activity. Substrates lacking phosphate or pyrophosphate linked to GlcNAc were inactive. The length of the aliphatic chain of acceptor substrates also contributes to the activity.

  O-antigen, gene cluster, Glucosyltransferases, enzymatic syntheses, Escherichia coli O56, Escherichia coli O152

  NCBI PubMed ID: 18487334
  Publication DOI: 10.1128/JB.00160-08
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: fenglu63@nankai.edu.cn
  Institutions: Department of Medicine, Department of Biochemistry, Queen's University, Kingston Ontario K7L 3N6, Canada, TEDA School of Biological Sciences and Biotechnology, Nankai University, Hongda Street, TEDA, Tianjin 300457, P.R.China, Tianjin Key Laboratory of Microbial Functional Genomics, P. R. China, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, P. R. China, Department of Chemistry, Queen's University, Kingston Ontario K7L 3N6, Canada
  Methods: 13C NMR, 1H NMR, genetic methods, biochemical methods, HPLC
  
   
  
  Escherichia coli O152
  CSDB ID 22850 (all data & tools)
• Article ID: 3505
  Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Wang Q, Reeves P, Wang L "Structure and genetics of Shigella O antigens" - FEMS Microbiology Reviews 32(4) (2008) 627-653
  

  This review covers the O antigens of the 46 serotypes of Shigella, but those of most Shigella flexneri are variants of one basic structure, leaving 34 Shigella distinct O antigens to review, together with their gene clusters. Several of the structures and gene clusters are reported for the first time and this is the first such group for which structures and DNA sequences have been determined for all O antigens. Shigella strains are in effect Escherichia coli with a specific mode of pathogenicity, and 18 of the 34 O antigens are also found in traditional E. coli. Three are very similar to E. coli O antigens and 13 are unique to Shigella strains. The O antigen of Shigella sonnei is quite atypical for E. coli and is thought to have transferred from Plesiomonas. The other 12 O antigens unique to Shigella strains have structures that are typical of E. coli, but there are considerably more anomalies in their gene clusters, probably reflecting recent modification of the structures. Having the complete set of structures and genes opens the way for experimental studies on the role of this diversity in pathogenicity.

  structure, O antigen, Shigella, O antigen gene cluster, O antigen diversity

  NCBI PubMed ID: 18422615
  Publication DOI: 10.1111/j.1574-6976.2008.00114.x
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: wanglei@nankai.edu.cn
  Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, serological methods, genetic methods, biochemical methods
  
   
  
  Shigella dysenteriae D12, Escherichia coli O152
  CSDB ID 23078 (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
  
   
  
  Citrobacter rodentium ATCC 51459
  CSDB ID 27499 (all data & tools)
• Article ID: 5472
  Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" - FEMS Microbiology Reviews 44(6) (2020) 655-683
  

  Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.

  structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity

  NCBI PubMed ID: 31778182
  Publication DOI: 10.1093/femsre/fuz028
  Journal NLM ID: 8902526
  Publisher: Oxford University Press
  Correspondence: G. Widmalm ; Lei Wang
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
  
   
  
  Escherichia coli O152, Shigella dysenteriae 12
  CSDB ID 1893 (all data & tools)