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Structure type: polymer chemical repeating unit
Trivial name: specific polysaccharide antigen (SPA), a-specific polysaccharide antigen
Compound class: O-polysaccharide

• Article ID: 1101
  Perry MB, Maclean LM, Brisson JR, Wilson ME "Structures of the antigenic O-polysaccharides of lipopolysaccharides produced by Actinobacillus actinomycetemcomitans serotypes a, c, d and e" - European Journal of Biochemistry 242(3) (1996) 682-688
  

  Actinobacillus actinomycetemcomitans is a gram-negative capnophilic coccobacillus that has been implicated in the etiology of certain forms of early-onset periodontitis as well as non-oral infections, mostly bacterial endocarditis. Five distinct serotypes of A. actinomycetemcomitans have been described. Although the O-polysaccharide (O-PS) of lipopolysaccharide (LPS) has been shown to define the serologic specificity for this species, only the structure of the O-PS of serotype b has been characterized. The focus of the current study was to define the structures of the O-PS of A. actinomycetemcomitans serotypes a, c, d and e. Structure determination was accomplished through the use of methylation, periodate oxidation, and one-dimensional and two-dimensional NMR methods. The O-PS of A. actinomycetemcomitans (OMZ-542) serotype d had [α]D +15 degrees and was composed of D-glucose, D-mannose and L-rhamnose (L-Rha) in a molar ratio of 1:2:1. Methylation, periodate oxidation, and two-dimensional 1H NMR and 13C NMR studies showed that the antigenic O-PS was a high-molecular-mass polymer composed of repeating tetrasaccharide units with the structure: [formula: see text] The O-PS of the LPS produced by A. actinomycetemcomitans (ATCC29523) serotype a had [α]D +150 degrees and was found to contain 6-deoxy-D-talose (6dTalp) and O-acetyl (2:1) and was a high-molecular-mass polymer composed of O-acetyl-substituted repeating disaccharide units with the structure: [formula: see text] The O-PS of the LPS of A. actinomycetemcomitans (SUNY 67) serotype c had [α]D -170 degrees and was composed of 6-deoxy-L-talose and O-acetyl (2:1). Structural analysis showed that the O-PS was a high-molecular-mass polymer of repeating disaccharide units with the structure: [formula: see text] The O-PS of the LPS of A. actinomycetemcomitans (OMZ 534) serotype e had [α]D +57 degrees and was composed of 2-acetamido-2-deoxy-D-glucose and L-rhamnose (1:1) and by chemical and NMR analysis was found to be a polymer of repeating disaccharide units with the structure: →4)-α-D-GlcpNAc-(1→3)-α-L-Rhap-(1→.

  Lipopolysaccharide, lipopolysaccharides, LPS, structure, serotype, O-polysaccharide, O polysaccharide, antigenic, Serotypes, Actinobacillus, Actinobacillus actinomycetemcomitans

  NCBI PubMed ID: 9022697
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Oral Biology, School of Dental Medicine, State University of New York at Buffalo, USA
  Methods: NMR-2D, NMR, paper chromatography
  
   
  
  Actinobacillus actinomycetemcomitans a (ATCC 29523)
  CSDB ID 4139 (all data & tools)
• Article ID: 1274
  Suzuki N, Nakano Y, Yoshida Y, Nezu T, Terada Y, Yamashita Y, Koga T "Guanosine diphosphate-4-keto-6-deoxy-d-mannose reductase in the pathway for the synthesis of GDP-6-deoxy-D-talose in Actinobacillus actinomycetemcomitans" - European Journal of Biochemistry 269(23) (2002) 5963-5971
  

  The serotype a-specific polysaccharide antigen of Actinobacillus actinomycetemcomitans is an unusual sugar, 6-deoxy-d-talose. Guanosine diphosphate (GDP)-6-deoxy-d-talose is the activated sugar nucleotide form of 6-deoxy-d-talose, which has been identified as a constituent of only a few microbial polysaccharides. In this paper, we identify two genes encoding GDP-6-deoxy-d-talose synthetic enzymes, GDP-α-D-mannose 4,6-dehydratase and GDP-4-keto-6-deoxy-d-mannose reductase, in the gene cluster required for the biosynthesis of serotype a-specific polysaccharide antigen from A. actinomycetemcomitans SUNYaB 75. Both gene products were produced and purified from Escherichia coli transformed with plasmids containing these genes. Their enzymatic reactants were analysed by reversed-phase HPLC (RP-HPLC). The sugar nucleotide produced from GDP-α-D-mannose by these enzymes was purified by RP-HPLC and identified by electrospray ionization-MS, 1H nuclear magnetic resonance, and GC/MS. The results indicated that GDP-6- deoxy-d-talose is produced from GDP-α-D-mannose. This paper is the first report on the GDP-6-deoxy-d-talose biosynthetic pathway and the role of GDP-4-keto-6-deoxy-d-mannose reductase in the synthesis of GDP- 6-deoxy-d-talose

  NMR, biosynthesis, synthesis, antigen, biosynthetic, gene, role, polysaccharide, serotype, form, Escherichia, Escherichia coli, cluster, gene cluster, electrospray, sugar, polysaccharides, enzymatic, nuclear, nuclear magnetic resonance, plasmid, resonance, enzyme, purified, Enzymes, pathway, Japan, Synthetic, Mannose, Actinobacillus, Actinobacillus actinomycetemcomitans, polysaccharide antigen, activated, 6-deoxy-D-talose, HPLC, Plasmids, oral, sugar nucleotide, 6-deoxytalose, microbial polysaccharides, serotype-specific antigen

  NCBI PubMed ID: 12444986
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: yosh+AEA-dent.kyushu-u.ac.jp
  Institutions: Department of Preventive Dentistry and Department of Prosthetic Dentistry I, Kyushu University Faculty of Dental Science, Fukuoka, Japan, Department of Oral Health, Nihon University School of Dentistry, Tokyo, Japan
  Methods: 1H NMR, ESI-MS
  
   
  
  Actinobacillus actinomycetemcomitans a (SUNYaB75)
  CSDB ID 4976 (all data & tools)
• Article ID: 2725
  Kawasaki M, Takamatsu N, Ansai T, Yamashita Y, Takehara T, Koga T "An enzyme-linked immunosorbent assay for measuring antibodies to serotype-specific polysaccharide antigens of Actinobacillus actinomycetemcomitans" - Journal of Microbiological Methods 21 (1995) 181-192
  

  An enzyme-linked immunosorbent assay utilizing avidin-biotin binding has been developed for measuring antibodies to serotype-specific polysaccharide antigens of Actinobacillus actinomycetemcomitans. The serotype a, b and c polysaccharide antigens were coupled with biotin via an adipic acid hydrazide functional group. The biotinylated antigens immobilized on the avidin-precoated wells reacted specifically with rabbit antisera to whole cells of the corresponding serotype of A. actinomycetemcomitans. Antibodies to the antigens in 1:6,400 to 1:12,800 dilutions of human sera from subjects with periodontitis could be detected by using the assay.

  Publication DOI: 10.1016/0167-7012(95)91417-D
  Journal NLM ID: 8306883
  WWW link: http://www.sciencedirect.com/science/article/pii/016770129591417D
  Institutions: Department of Preventive Dentistry, Kyushu University Faculty of Dentistry, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812, Japan
  
   
  
  Actinobacillus actinomycetemcomitans a (ATCC 29523)
  CSDB ID 140608 (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
  
   
  
  Aggregatibacter actinomycetemcomitans a
  CSDB ID 27705 (all data & tools)
• Article ID: 4433
  Shibuya N, Amano K, Azuma J, Nishihara T, Kitamura Y, Noguchi T, Koga T "6-Deoxy-D-talan and 6-deoxy-L-talan. Novel serotype-specific polysaccharide antigens from Actinobacillus actinomycetemcomitans" - Journal of Biological Chemistry 266(25) (1991) 16318-16323
  

  Serotype-specific polysaccharide antigens from Actinobacillus actinomycetemcomitans ATCC 29523 (serotype a) and NCTC 9710 (serotype c) were extracted from whole cells by autoclaving and purified by ion-exchange chromatography and gel filtration. Analysis of component sugars by gas-liquid chromatography-mass spectrometry, high performance liquid chromatography, and NMR together with optical rotation data showed that the serotype a antigen was composed solely of 6-deoxy-D-talose, whereas the serotype c antigen consisted of 6-deoxy-L-talose. Structural analysis indicated that both of these antigens were composed of closely related repeating units, -3)-6-deoxy-α-D-Talp-(1-2)-6-deoxy-α-D-Talp-(1-(sero type a) and -3)-6-deoxy-α-L-Talp-(1-2)-6-deoxy-α-L-Talp-(1-(sero type c). 1H and 13C NMR analysis showed that both of these serotype antigens contained one acetyl group/2 sugar residues. These acetyl groups localized at the O-2 position of 3-linked 6-deoxy-D-talose (serotype a) or O-4 position of 3-linked 6-deoxy-L-talose residues (serotype c), respectively. These results coupled with our previous findings on the serotype b antigen (Amano, K., Nishihara, T., Shibuya, N., Noguchi, T., and Koga, T. (1989) Infect. Immun. 57, 2942-2946) showed that the serotype antigens from A. actinomycetemcomitans are a group of novel polysaccharides with structural features closely related biosynthetically.

  6-deoxy-L-talose, Actinobacillus actinomycetemcomitans, polysaccharide antigen, 6-deoxy-D-talose, serotype-specific

  NCBI PubMed ID: 1885566
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: National Food Research Institute, Ministry of Agriculture, Forestry and Fisheries, Tsukuba, Japan
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, GLC, HPLC
  
   
  
  Actinobacillus actinomycetemcomitans a (ATCC 29523)
  CSDB ID 27380 (all data & tools)

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

• Article ID: 4307
  Greenfield LK, Whitfield C "Synthesis of lipopolysaccharide O-antigens by ABC transporter-dependent pathways" - Carbohydrate Research 356 (2012) 12-24
  

  The O-polysaccharide (O-PS; O-antigen) of bacterial lipopolysaccharides is made up of repeating units of one or more sugar residues and displays remarkable structural diversity. Despite the structural variations, there are only three strategies for O-PS assembly. The ATP-binding cassette (ABC)-transporter-dependent mechanism of O-PS biosynthesis is widespread. The Escherichia coli O9a and Klebsiella pneumoniae O2a antigens provide prototypes, which are distinguished by the fine details that link glycan polymerization and chain termination at the cytoplasmic face of the inner membrane to its export via the ABC transporter. Here, we describe the current understanding of these processes. Since glycoconjugate assembly complexes that utilize an ABC transporter-dependent pathway are widespread among the bacterial kingdom, the models described here are expected to extend beyond O-PS biosynthesis systems

  Lipopolysaccharide, O-polysaccharide, ATP-binding cassette transporter, Escherichia coli O9a, Klebsiella pneumoniae O2a

  NCBI PubMed ID: 22475157
  Publication DOI: 10.1016/j.carres.2012.02.027
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: C. Whitfield
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1
  
   
  
  Aggregatibacter actinomycetemcomitans a
  CSDB ID 28371 (all data & tools)