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Structure type: polymer chemical repeating unit
Trivial name: teichoic acid, anionic polysaccharide, glycosyl 1-phosphate polymer (GPP)
Compound class: CPS, K-antigen, cell wall polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_241118,IEDB_885822,IEDB_983931,SB_192

• Article ID: 1717
  Altman E, Brisson JR, Perry MB "Structural studies of the capsular polysaccharide from Actinobacillus (Haemophilus) pleuropneumoniae serotype 4" - Biochemistry and Cell Biology 66 (1988) 998-1004
  

  The capsular polysaccharide of Actinobacillus (Haemophilus pleuropneumoniae serotype 4 (ATCC 33378) is composed of D-glucose (one part), 2-acetamido-2-deoxy-D-galactose (one part), and phosphate (one part). From hydrolysis, dephosphorylation, methylation, and 1H and 13C nuclear magnetic resonance studies, the polysaccharide was found to be a high molecular weight polymer of a repeating disaccharide unit, joined through monophosphate diester linkages and having the following structure: [formula: see text].

  Publication DOI: 10.1139/o88-114
  Journal NLM ID: 8606068
  Publisher: Ottawa: National Research Council of Canada
  Institutions: Division of Biological Sciences, National Research Council, Ottawa, Ont., Canada
  Methods: 13C NMR, 1H NMR
  
   
  
  Actinobacillus pleuropneumoniae 4
  CSDB ID 105799 (all data & tools)
• Article ID: 3365
  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.
  
   
  
  Actinobacillus pleuropneumoniae 4
  CSDB ID 21763 (all data & tools)
• Article ID: 3779
  Shashkov AS, Potekhina NV, Senchenkova SN, Kudryashova EB "Anionic polymers of the cell wall of Bacillus subtilis subsp. subtilis VKM B-501(T)" - Biochemistry 74(5) (2009) 543-548
  

  Teichoic acid and disaccharide-1-phosphate polymer were identified in the cell walls of Bacillus subtilis subsp. subtilis VKM B-501(T). The teichoic acid represents 1,3-poly(glycerol phosphate) 80% substituted by α-D-glucopyranose residues at O-2 of glycerol. The linear repeating unit of disaccharide-1-phosphate polymer contains the residues of β-D-glucopyranose, N-acetyl-α-D-galactosamine, and phosphate and has the following structure: -6)-β-D-Glcp-(1→3)-α-D-GalpNAc-(1-P-. The structures of two anionic polymers were determined by chemical and NMR-spectroscopic methods. The 1H- and 13C-NMR spectral data on disaccharide-1-phosphate polymer are presented for the first time.

  NMR spectroscopy, cell wall, teichoic acid, Bacillus subtilis, anionic polysaccharides, disaccharide-1-phosphate polymer

  NCBI PubMed ID: 19538128
  Publication DOI: 10.1134/s0006297909050095
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: potekhina@hotbox.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, enzymatic hydrolysis, 31P NMR, acid hydrolysis, paper chromatography, electrophoresis
  
   
  
  Bacillus subtilis VKM B-501
  CSDB ID 24232 (all data & tools)
• Article ID: 4099
  Potekhina NV, Streshinskaia GM, Tul'skaya EM, Kozlova YI, Senchenkova SN, Shashkov AS "Phosphate-containing polymers of cell wall of bacilli" - Biochemistry (Moscow) 76(7) (2011) 745-754
  

  Anionic phosphate-containing cell wall polymers of bacilli are represented by teichoic acids and poly(glycosyl 1-phosphates). Different locations of phosphodiester bonds in the main chain of teichoic acids as well as the nature and combination of the constituent structural elements underlie their structural diversity. Currently, the structures of teichoic acids of bacilli can be classified into three types, viz. poly(polyol phosphates) with glycerol or ribitol as the polyol; poly(glycosylpolyol phosphates), mainly glycerol-containing polymers; and poly(acylglycosylglycerol phosphate), in which the components are covalently linked through glycosidic, phosphodiester, and amide bonds. In addition to teichoic acids, poly(glycosyl 1-phosphates) with mono- and disaccharide residues in the repeating units have been detected in cell walls of several Bacillus subtilis and Bacillus pumilus strains. The known structures of teichoic acids and poly(glycosyl 1-phosphates) of B. subtilis, B. atrophaeus, B. licheniformis, B. pumilus, B. stearothermophilus, B. coagulans, B. cereus as well as oligomers that link the polymers to peptidoglycan are surveyed. The reported data on the structures of phosphate-containing polymers of different strains of B. subtilis suggest heterogeneity of the species and may be of interest for the taxonomy of bacilli to allow differentiation of closely related organisms according to the 'structures and composition of cell wall polymers' criterion.

  cell wall, teichoic acids, Bacillus, poly(glycosyl 1-phosphates)

  NCBI PubMed ID: 21999535
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: potekchina@hotbox.ru
  Institutions: Lomonosov Moscow State University, Russia
  
   
  
  Bacillus subtilis 168, Bacillus subtilis ssp. subtilis VKM B-501T
  CSDB ID 26938 (all data & tools)
• Article ID: 4115
  Streshinskaya GM, Shashkov AS, Potekhina NV, Kozlova YI, Tul'skaya EM, Senchenkova SN, Kudryashova EB, Anan'ina LN "Carbohydrate-containing cell wall polymers of some strains of the Bacillus subtilis group" - Mikrobiologiia = Microbiology [Russian] 80(1) (2011) 21-29
  

  A comparative study of the structures of carbohydrate-containing cell wall polymers isolated from the strains of the Bacillus subtilis group was performed by means of chemical and NMR spectroscopic meth ods. Polymers of different structure were revealed, namely, 1,3-poly(glycerol phosphates) with β-glucopyranose in Bacillus subtilis strains VKM B-520, VKM B-723, and VKM B-763 (= VKM B-911); 1,5-poly(ribitol phosphate) with α-glucopyranose in B. subtilis strains VKM B-722 and VKM B-922 (the structure is reported for the first time); and simultaneously two polymers in B. subtilis VKM B-761, 1,5-poly(ribitol phosphate) with β-glucopyranose and the disaccharide 1-phosphate polymer with the following repeating unit: -6)-α-D-Galp-(1-P-4)-gB-D-GlcpNAc-(1-, in which the hydroxyls at C3 and C6 of glucosamine residues are partially O-acetylated (the structure is reported for the first time). Heterogeneity of the B. subtilis group is con firmed by variations in the structure and composition of the cell wall polymers. The cell surface polymers are useful for discrimination of closely related bacilli strains and are cell wall marker components that may be an indispensable element of the Bacillus subtilis group taxonomy along with the genomosystematic methods.

  NMR spectroscopy, cell wall, teichoic acid, Bacillus subtilis, taxonomy, disaccharide 1-phosphate polymer

  Publication DOI: 10.1134/S0026261711010164
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: streshinskaya@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, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Institute of Ecology and Genetics of Microorganisms, Ural Division Russian Academy of Sciences Perm Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, paper chromatography, NMR-1D, electrophoresis, RNA sequencing
  
   
  
  Bacillus subtilis ssp. subtilis VKM B-501T
  CSDB ID 26487 (all data & tools)
• Article ID: 4398
  Streshinskaya GM, Shashkov AS, Kozlova YI, Tul'skaya EM, Kudryashova EB, Senchenkova SN, Ariskina EV, Evtushenko LI, Potekhina NV "Cell wall teichoic acids of Bacillus licheniformis VKM B-511T, Bacillus pumilus VKM B-508T, and other strains previously assigned to Bacillus pumilus" - Mikrobiologiia = Microbiology [Russian] 81(4) (2012) 425-434
  

  The teichoic acids (TAs) of type strains, viz. Bacillus licheniformis VKM B-511T and Bacillus pumilus VKM B-508T, as well as phylogenetically close bacteria VKM B-424, VKM B-1554, and VKM B-711 previously assigned to Bacillus pumilus on the basis of morphological, physiological, and biochemical properties, were investigated. Three polymers were found in the cell wall of each of the 5 strains under study. Strains VKM B-508T, VKM B-424, and VKM B-1554 contained polymers of the same core: unsubstituted 1,3-poly(glycerol phosphate) (TA I) and 1,3-poly(glycerol phosphate) with O-D-Ala and N-acetyl-a-D-glucosamine substituents (TA II and TA III', respectively). The cell walls of two remaining strains contained TA I, TA II, and a poly(glycosylpolyol phosphate) with the following structure of repeating units: -6)-a-D-GlcpNAc(1-1)-snGro-(3-P-(TA III'') in 'Bacillus pumilus' VKM B-711 (100% 16S rRNA gene similarity with the type strain of Bacillus safensis) and -6)-a-D-Galp-(1-2)-snGro-(3-P-(TA III''') in Bacillus licheniformis VKM B-511T. The simultaneous presence of three different TAs in the cell walls was confirmed by the NMR spectroscopic DOSY methods. The structure of the polymers and localization of O-D-Ala residues were investigated by the chemical and NMR spectroscopic methods.

  NMR spectroscopy, teichoic acid, Bacillus licheniformis, taxonomy, Bacillus pumilus

  Publication DOI: 10.1134/S0026261712030125
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: streshinskaya@mail.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, paper chromatography, composition analysis, genetic methods, paper electrophoresis
  
   
  
  Bacillus subtilis ssp. subtilis VKM B-501
  CSDB ID 28641 (all data & tools)
• Article ID: 4434
  Perry MB, Altman E, Brisson JR "Structural caharacteristics of the antigenic capsular polysaccharides and lipopolysaccharides involved in the serological classification of Actinobacillus (Haemophilus) pleuropneumoniae strains" - Serodiagnosis and Immunotherapy in Infectious Disease 4 (1990) 299-308
  

  The detailed structures of the specific capsular polysaccharides and cellular lipopolysaccharides of the 12 known serotypes of Actinobacillus (Haemophilus) pleuropneumoniae are presented and their serological relationships are discussed together with their significance in the control of swine pleuropneumonia.

  lipopolysaccharides, polysaccharides, capsules, Actinobacillus (Haemophilus) pleuropneumoniae

  Publication DOI: 10.1016/0888-0786(90)90018-J
  Journal NLM ID: 8707525
  Publisher: London; Orlando: Academic Press
  Institutions: Institute for Biological Sciences, National Research Council Canada, Ottawa, Ont., Canada K1A 0R6
  Methods: serological methods
  
   
  
  Actinobacillus pleuropneumoniae 4
  CSDB ID 28800 (all data & tools)
• Article ID: 4605
  Potekhina NV, Shashkov AS, Streshinskaia GM, Tul'skaya EM, Senchenkova SN, Kudryashova EB, Dmitrenok AS "Disaccharide 1-phosphate polymers of some representatives of the Bacillus subtilis group" - Biochemistry (Moscow) 78(10) (2013) 1146-1154
  

  Disaccharide 1-phosphate polymers as well as teichoic acids of various structures have been found in the cell walls of the representatives of the Bacillus subtilis group, namely Bacillus subtilis subsp. spizizenii VKM B-720 and VKM B-916, B. subtilis VKM B-517, and Bacillus vallismortis VKM B-2653(T). Disaccharide 1-phosphate polymers are composed of repeating units of the following structure: -P-4)-β-D-GlcpNAc-(1→6)-α-D-Galp-(1-, the N-acetylglucosamine residues are partially acetylated at positions O3 and O6 (VKM B-720 and VKM B-916); -P-4)-β-D-Glcp-(1→6)-α-D-GlcpNAc-(1-, the glucopyranose residues are partially acetylated at positions O2 or O3 (VKM B-517); -P-6)-α-D-GlcpNH3(+)/α-D-GlcpNAc-(1→2)-α-D-Glcp-(1-, the N-acetylglucosamine residues are partially deacetylated (VKM B-2653(T)). The structures of the two last disaccharide 1-phosphate polymers have not been reported so far for Gram-positive bacteria. The teichoic acids in the studied strains are O-D-alanyl-1,5-poly(ribitol phosphates) substituted with β-D-glucopyranose (VKM B-517, VKM B-720, VKM B-916) or 2-acetamido-2-deoxy-β-D-glucopyranose (VKM B-2653(T)). The structures of the phosphate-containing polymers have been studied by chemical methods and by NMR spectroscopy.

  NMR spectroscopy, teichoic acids, Bacillus subtilis, glycosyl 1-phosphate polymers, Bacillus subtilis subsp. spizizenii, Bacillus vallismortis

  NCBI PubMed ID: 24237149
  Publication DOI: 10.1134/S000629791310009X
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: potekhina56@mail.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia, All-Russian Collection of Microorganisms, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, pr. Nauki 5, 142290, Pushchino, Moscow Region, Russia, fax: (495) 9394309
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, acid hydrolysis, paper chromatography, NMR-1D, paper electrophoresis
  
   
  
  Bacillus subtilis VKM B-501T
  CSDB ID 29738 (all data & tools)