Show legend Show as text

Structure type: polymer chemical repeating unit ; 7600
Compound class: teichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_141807,IEDB_151531,IEDB_1597446

• Article ID: 130
  Tul'skaya EM, Shashkov AS, Evtushenko LI, Taran VV, Naumova IB "Novel cell-wall teichoic acid from Nocardiopsis albus subsp. albus as a species-specific marker" - Microbiology 141 (1995) 1851-1856
  

  Cell walls of the three Nocardiopsis albus subsp. albus strains, DSM 43377T, 43378 and 43120 contain structurally identical teichoic acids. The cell wall of each strain has three distinct types of teichoic acids: (1) unsubstituted 3,5-poly(ribitol phosphate), (2) 1,3-poly(glycerol phosphate) partially substituted at C-2 with a-N-acetylglucosamine residues, and (3) 1,5-poly(ribitol phosphate) with each ribitol unit carrying a 2,4-pyruvate ketal group. Types 1 and 3 are reported in prokaryotes for the first time. The structure of the teichoic acids was elucidated by chemical analysis and NMR-spectroscopic methods. Structural identity of the teichoic acids from the three strains belonging to the same species may demonstrate the species-specificity of these polymers.

  NMR spectroscopy, Nocardiopsis, cell walls, teichoic acids, 3, 5-poly(ribitol phosphate), pyruvic acid

  Publication DOI: 10.1099/13500872-141-8-1851
  Journal NLM ID: 0376646
  Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Biology, Moscow State University, Moscow, Russia, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, Russia
  Methods: NMR-2D, NMR, electrophoresis
  
   
  
  Nocardiopsis albus ssp. albus DSM 43377T
  CSDB ID 5336 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit ; ~7600
Compound class: teichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_141807,IEDB_151531,IEDB_1597446

• Article ID: 131
  Tul'skaya EM, Shashkov AS, Evtushenko LI, Taran VV, Naumova IB "Teichoic acid from the cell wall of Nocardia albus ssp. albus DSM 43120" - Biochemistry (Moscow) 60 (1995) 125-130
  

  The cell walls of Nocardiopsis albus subsp. albus DSM 43120 contains three structurally distinct teichoic acids: unsubstituted 3,5-poly(ribitol phosphate) (I), 1,3-poly(glycerol phosphate) partially substituted with a-N-acetylglucosamine (II), and 1,5-poly(ribitol phosphate) with each unit carrying a 2,4-pyruvate ketal group (III). Teichoic acids of types I and II are here reported in prokaryotes for the first time. The structure of the teichoic acids was established by chemical methods and NMR spectroscopy.

  NMR spectroscopy, Nocardiopsis, cell walls, teichoic acids, 3, 5-poly(ribitol phosphate), pyruvic acid

  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, Russia, School of Biology, Lomonosov Moscow State University, Moscow, Russia, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, Russia.
  Methods: NMR-2D, NMR, paper chromatography, electrophoresis
  
   
  
  Nocardiopsis albus ssp. albus DSM 43120
  CSDB ID 5498 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: teichoic acid
Contained glycoepitopes: IEDB_130648,IEDB_130695,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_1597446,IEDB_885822

• Article ID: 352
  Potekhina NV, Shashkov AS, Evtushenko LI, Naumova IB "Teichoic acids in the cell walls of Microbispora mesophila Ac-1953T and Thermobifida fusca Ac-1952T" - Mikrobiologiia = Microbiology [Russian] 72(2) (2003) 189-193
  

  The cell walls of Microbispora mesophila strain Ac-1953T (the family Streptosporangiaceae) and Thermobifida fusca Ac-1952T (the family Nocardiopsiceae) were found to contain teichoic acids of a poly(glycerol phosphate) nature. The teichoic acid of M. mesophila (formerly Thermomonospora mesophila) represents a poly(glycerol phosphate) containing 5% of substituent 2-acetamido-2-deoxy-α-galactosaminyl residues. The teichoic acid of such kind was found in actinomycetes for the first time. The cell wall of T. fusca (formerly Thermonospora fusca) contains two teichoic acids, namely, unsubstituted 1,3-poly(glycerol phosphate) and β-glucosylated 1,3-poly(glycerol phosphate).

  structure, Bacterial, repeating unit, polysaccharides, chain, phosphate, cluster, teichoic acids, cell wall polysaccharides, mannan, taxonomic, teichuronic acid

  NCBI PubMed ID: 12751242
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: naumova@microbiol.bio.msu.su
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Faculty of Biology, Moscow State University, Morob'evy fory, Moscow, 119899 Russia, Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia
  Methods: NMR, chemical methods
  
   
  
  Microbispora mesophila Ac-1953T, Microbispora mesophila Ac-1952T
  CSDB ID 8028 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_1597446,IEDB_190606,SB_7

• Article ID: 475
  MacLean LL, Perry MB, Vinogradov E "Characterization of the antigenic lipopolysaccharide O chain and the capsular polysaccharide produced by Actinobacillus pleuropneumoniae serotype 13" - Infection and Immunity 72(10) (2004) 5925-5930
  

  Serotyping of Actinobacillus pleuropneumoniae, the etiologic agent of porcine pleuropneumonia, is important for epidemiological studies and for the development of homologous vaccine cell preparations. The serology is based on the specific chemical structures of capsular polysaccharides (CPSs) and lipopolysaccharide (LPS) antigenic O-polysaccharide moieties (O-PSs), and knowledge of these structures is required for a molecular-level understanding of their serological specificities. The structures of A. pleuropneumoniae serotype 1 to 12 CPSs and O-PSs have been elucidated; however, the structures associated with three newly proposed serotypes (serotypes 13, 14, and 15) have not been reported. Herein we described the structures of the antigenic O-PS and CPS of A. pleuropneumoniae serotype 13. The O-PS of the A. pleuropneumoniae serotype 13 LPS is a polymer of branched tetrasaccharide repeating units composed of l-rhamnose, 2-acetamido-2-deoxy-d-galactose, and d-galactose residues (1:1:2). By use of hydrolysis, methylation, and periodate oxidation chemical methods together with the application of one- and two-dimensional 1H and 13C nuclear magnetic resonance spectroscopy and mass spectrometry, the structures of the O chain and CPS were determined. The CPS of A. pleuropneumoniae serotype 13 was characterized as a teichoic-acid type polymer. The LPS O antigen was identical to the O-PS produced by A. pleuropneumoniae serotype 7. The CPS has the unique structure of a 1,3-poly(glycerol phosphate) teichoic acid type I polymer and constitutes the macromolecule defining the A. pleuropneumoniae serotype 13 antigenic specificity.

  capsular polysaccharide, serotyping, vaccine, 2-acetamido-2-deoxy-D-galactose, Actinobacillus pleuropneumoniae, Bacterial Capsules

  NCBI PubMed ID: 15385495
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: malcolm.perry@nrc-cnrc.gc.ca
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
  Methods: NMR-2D, methylation, NMR, dephosphorylation, Smith degradation, de-O-acetylation
  
   
  
  Actinobacillus pleuropneumoniae 13
  CSDB ID 9043 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_1597446,IEDB_190606,SB_7

• Article ID: 475
  MacLean LL, Perry MB, Vinogradov E "Characterization of the antigenic lipopolysaccharide O chain and the capsular polysaccharide produced by Actinobacillus pleuropneumoniae serotype 13" - Infection and Immunity 72(10) (2004) 5925-5930
  

  Serotyping of Actinobacillus pleuropneumoniae, the etiologic agent of porcine pleuropneumonia, is important for epidemiological studies and for the development of homologous vaccine cell preparations. The serology is based on the specific chemical structures of capsular polysaccharides (CPSs) and lipopolysaccharide (LPS) antigenic O-polysaccharide moieties (O-PSs), and knowledge of these structures is required for a molecular-level understanding of their serological specificities. The structures of A. pleuropneumoniae serotype 1 to 12 CPSs and O-PSs have been elucidated; however, the structures associated with three newly proposed serotypes (serotypes 13, 14, and 15) have not been reported. Herein we described the structures of the antigenic O-PS and CPS of A. pleuropneumoniae serotype 13. The O-PS of the A. pleuropneumoniae serotype 13 LPS is a polymer of branched tetrasaccharide repeating units composed of l-rhamnose, 2-acetamido-2-deoxy-d-galactose, and d-galactose residues (1:1:2). By use of hydrolysis, methylation, and periodate oxidation chemical methods together with the application of one- and two-dimensional 1H and 13C nuclear magnetic resonance spectroscopy and mass spectrometry, the structures of the O chain and CPS were determined. The CPS of A. pleuropneumoniae serotype 13 was characterized as a teichoic-acid type polymer. The LPS O antigen was identical to the O-PS produced by A. pleuropneumoniae serotype 7. The CPS has the unique structure of a 1,3-poly(glycerol phosphate) teichoic acid type I polymer and constitutes the macromolecule defining the A. pleuropneumoniae serotype 13 antigenic specificity.

  capsular polysaccharide, serotyping, vaccine, 2-acetamido-2-deoxy-D-galactose, Actinobacillus pleuropneumoniae, Bacterial Capsules

  NCBI PubMed ID: 15385495
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Correspondence: malcolm.perry@nrc-cnrc.gc.ca
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada
  Methods: NMR-2D, methylation, NMR, dephosphorylation, Smith degradation, de-O-acetylation
  
   
  
  Actinobacillus pleuropneumoniae 13
  CSDB ID 9097 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: CWP
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130695,IEDB_141807,IEDB_151531,IEDB_1597446

• Article ID: 487
  Kuebler-Kielb J, Coxon B, Schneerson R "Chemical structure, conjugation, and cross-reactivity of Bacillus pumilus Sh18 cell wall polysaccharide" - Journal of Bacteriology 186(20) (2004) 6891-6901
  

  Bacillus pumilus strain Sh18 cell wall polysaccharide (CWP), cross-reactive with the capsular polysaccharide of Haemophilus influenzae type b, was purified and its chemical structure was elucidated using fast atom bombardment mass spectrometry, nuclear magnetic resonance techniques, and sugar-specific degradation procedures. Two major structures, 1,5-poly(ribitol phosphate) and 1,3-poly(glycerol phosphate), with the latter partially substituted by 2-acetamido-2-deoxy-α-galactopyranose (13%) and 2-acetamido-2-deoxy-α-glucopyranose (6%) on position O-2, were found. A minor component was established to be a polymer of →3-O-(2-acetamido-2-deoxy-β-glucopyranosyl)-1→4-ribitol-1-OPO3→. The ratios of the three components were 56, 34, and 10 mol%, respectively. The Sh18 CWP was covalently bound to carrier proteins, and the immunogenicity of the resulting conjugates was evaluated in mice. Two methods of conjugation were compared: (i) binding of 1-cyano-4-dimethylaminopyridinium tetrafluoroborate-activated hydroxyl groups of the CWP to adipic acid dihydrazide (ADH)-derivatized protein, and (ii) binding of the carbodiimide-activated terminal phosphate group of the CWP to ADH-derivatized protein. The conjugate-induced antibodies reacted in an enzyme-linked immunosorbent assay with the homologous polysaccharide and with a number of other bacterial polysaccharides containing ribitol and glycerol phosphates, including H. influenzae types a and b and strains of Staphylococcus aureus and Staphylococcus epidermidis.

  Haemophilus influenzae, structure, capsular polysaccharide, polysaccharides, antibodies, spectrometry, cell wall, Staphylococcus, conjugate, Bacillus, cross-reactivity, Bacterial Vaccines

  NCBI PubMed ID: 15466043
  Publication DOI: 10.1128/JB.186.20.6891-6901.2004
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: kielbj@mail.nih.gov
  Institutions: Laboratory of Developmental and Molecular Immunity, NIH/NICHD,9000 Rockville Pike, Bldg. 6, Rm. 1A05, Bethesda, MD, USA
  Methods: NMR-2D, FAB-MS, NMR, HF solvolysis, mild acid hydrolysis, Smith degradation
  
   
  
  Bacillus pumilus Sh18
  CSDB ID 9060 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: CWP
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130695,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_1597446,IEDB_885822

• Article ID: 487
  Kuebler-Kielb J, Coxon B, Schneerson R "Chemical structure, conjugation, and cross-reactivity of Bacillus pumilus Sh18 cell wall polysaccharide" - Journal of Bacteriology 186(20) (2004) 6891-6901
  

  Bacillus pumilus strain Sh18 cell wall polysaccharide (CWP), cross-reactive with the capsular polysaccharide of Haemophilus influenzae type b, was purified and its chemical structure was elucidated using fast atom bombardment mass spectrometry, nuclear magnetic resonance techniques, and sugar-specific degradation procedures. Two major structures, 1,5-poly(ribitol phosphate) and 1,3-poly(glycerol phosphate), with the latter partially substituted by 2-acetamido-2-deoxy-α-galactopyranose (13%) and 2-acetamido-2-deoxy-α-glucopyranose (6%) on position O-2, were found. A minor component was established to be a polymer of →3-O-(2-acetamido-2-deoxy-β-glucopyranosyl)-1→4-ribitol-1-OPO3→. The ratios of the three components were 56, 34, and 10 mol%, respectively. The Sh18 CWP was covalently bound to carrier proteins, and the immunogenicity of the resulting conjugates was evaluated in mice. Two methods of conjugation were compared: (i) binding of 1-cyano-4-dimethylaminopyridinium tetrafluoroborate-activated hydroxyl groups of the CWP to adipic acid dihydrazide (ADH)-derivatized protein, and (ii) binding of the carbodiimide-activated terminal phosphate group of the CWP to ADH-derivatized protein. The conjugate-induced antibodies reacted in an enzyme-linked immunosorbent assay with the homologous polysaccharide and with a number of other bacterial polysaccharides containing ribitol and glycerol phosphates, including H. influenzae types a and b and strains of Staphylococcus aureus and Staphylococcus epidermidis.

  Haemophilus influenzae, structure, capsular polysaccharide, polysaccharides, antibodies, spectrometry, cell wall, Staphylococcus, conjugate, Bacillus, cross-reactivity, Bacterial Vaccines

  NCBI PubMed ID: 15466043
  Publication DOI: 10.1128/JB.186.20.6891-6901.2004
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: kielbj@mail.nih.gov
  Institutions: Laboratory of Developmental and Molecular Immunity, NIH/NICHD,9000 Rockville Pike, Bldg. 6, Rm. 1A05, Bethesda, MD, USA
  Methods: NMR-2D, FAB-MS, NMR, HF solvolysis, mild acid hydrolysis, Smith degradation
  
   
  
  Bacillus pumilus Sh18
  CSDB ID 9061 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: CWP
Compound class: O-polysaccharide, cell wall polysaccharide, teichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_1597446

• Article ID: 487
  Kuebler-Kielb J, Coxon B, Schneerson R "Chemical structure, conjugation, and cross-reactivity of Bacillus pumilus Sh18 cell wall polysaccharide" - Journal of Bacteriology 186(20) (2004) 6891-6901
  

  Bacillus pumilus strain Sh18 cell wall polysaccharide (CWP), cross-reactive with the capsular polysaccharide of Haemophilus influenzae type b, was purified and its chemical structure was elucidated using fast atom bombardment mass spectrometry, nuclear magnetic resonance techniques, and sugar-specific degradation procedures. Two major structures, 1,5-poly(ribitol phosphate) and 1,3-poly(glycerol phosphate), with the latter partially substituted by 2-acetamido-2-deoxy-α-galactopyranose (13%) and 2-acetamido-2-deoxy-α-glucopyranose (6%) on position O-2, were found. A minor component was established to be a polymer of →3-O-(2-acetamido-2-deoxy-β-glucopyranosyl)-1→4-ribitol-1-OPO3→. The ratios of the three components were 56, 34, and 10 mol%, respectively. The Sh18 CWP was covalently bound to carrier proteins, and the immunogenicity of the resulting conjugates was evaluated in mice. Two methods of conjugation were compared: (i) binding of 1-cyano-4-dimethylaminopyridinium tetrafluoroborate-activated hydroxyl groups of the CWP to adipic acid dihydrazide (ADH)-derivatized protein, and (ii) binding of the carbodiimide-activated terminal phosphate group of the CWP to ADH-derivatized protein. The conjugate-induced antibodies reacted in an enzyme-linked immunosorbent assay with the homologous polysaccharide and with a number of other bacterial polysaccharides containing ribitol and glycerol phosphates, including H. influenzae types a and b and strains of Staphylococcus aureus and Staphylococcus epidermidis.

  Haemophilus influenzae, structure, capsular polysaccharide, polysaccharides, antibodies, spectrometry, cell wall, Staphylococcus, conjugate, Bacillus, cross-reactivity, Bacterial Vaccines

  NCBI PubMed ID: 15466043
  Publication DOI: 10.1128/JB.186.20.6891-6901.2004
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: kielbj@mail.nih.gov
  Institutions: Laboratory of Developmental and Molecular Immunity, NIH/NICHD,9000 Rockville Pike, Bldg. 6, Rm. 1A05, Bethesda, MD, USA
  Methods: NMR-2D, FAB-MS, NMR, HF solvolysis, mild acid hydrolysis, Smith degradation
  
   
  
  Bacillus pumilus Sh18, Bacillus pumilus Sh17
  CSDB ID 9062 (all data & tools)
• Article ID: 5225
  Velichko NS, Surkina AK, Fedonenko YP, Zdorovenko EL, Konnova SA "Structural peculiarities and biological properties of the lipopolysaccharide from Herbaspirillum seropedicae Z78" - Mikrobiologiia = Microbiology [Russian] 87(5) (2018) 635-641
  

  Lipopolysaccharide was isolated by phenol extraction from the surface membrane of the nitrogen-fixing endophytic rhizobacterium Herbaspirillum seropedicae, strain Z78. The lipopolysaccharide's lipid A contained 3-hydroxydecanoic, 3-hydroxydodecanoic, dodecanoic, tetradecanoic, and hexadecanoic acids. The 3-hydroxydodecanoic acid was amide-linked to the sugar backbone of the lipid A. The structure of the O-polysaccharide from H. seropedicae Z78 was established for the first time. It is characterized by heterogeneity and by the presence of glycerol, a component rarely found in gram-negative bacteria. The O polysaccharide of H. seropedicae Z78 was found to consist of two types of repeating units: one represented by glycerol-1-phosphate and the other by the glycerol-1-phosphate of the backbone, which is substituted at the 2-position by N-acetyl-D-glucosamine. The lipopolysaccharide of the H. seropedicae Z78 was weakly toxic to warm-blooded animals and moderately and dose-dependently induced interleukin synthesis by human whole blood cells and NO synthesis by mouse splenocytes. This may indicate that the H. seropedicae lipopolysaccharide is a promising antagonist of classical endotoxins.

  Lipopolysaccharide, structure, O-polysaccharide, Herbaspirillum seropedicae

  Publication DOI: 10.1134/S002626171805017
  Journal NLM ID: 0376652
  Publisher: Moskva: Izdatelstvo Nauka
  Correspondence: velichko-n@ibppm.ru
  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 Saratov Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, 31P NMR, GLC, composition analysis, HF treatment, mild acid degradation, cytokine production
  
   
  
  Herbaspirillum seropedicae Z78 (IBPPM217)
  CSDB ID 12809 (all data & tools)
• Article ID: 5226
  Vinogradov E, Sadovskaya I, Courtin P, Kulakauskas S, Grard T, Mahony J, van Sinderen D, Chapot-Chartier MP "Determination of the cell wall polysaccharide and teichoic acid structures from Lactococcus lactis IL1403" - Carbohydrate Research 462 (2018) 39-44
  

  In the lactic acid bacterium Lactococcus lactis, a cell wall polysaccharide (CWPS) is the bacterial receptor of the majority of infecting bacteriophages. The diversity of CWPS structures between strains explains, at least partially, the narrow host range of lactococcal phages. In the present work, we studied the polysaccharide components of the cell wall of the prototype L. lactis subsp. lactis strain IL1403. We identified a rhamnose-rich complex polysaccharide, carrying a glycerophosphate substitution, as the major component. Its structure was analyzed by 2D NMR spectroscopy, methylation analysis and MALDI-TOF MS and shown to be distinctly different from currently known lactococcal CWPS structures. It contains a linear backbone of repeated α-l-Rha disaccharide subunits, which is irregularly substituted with a trisaccharide occasionally bearing a glycerophosphate group. A poly (glycerol phosphate) teichoic acid, another important carbohydrate component of the IL1403 cell wall, was also isolated and structurally characterized.

  structure, NMR spectroscopy, Lactococcus lactis, rhamnose, Cell-wall polysaccharide

  NCBI PubMed ID: 29674103
  Publication DOI: 10.1016/j.carres.2018.04.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: M.-P. Chapot-Chartier
  Institutions: School of Microbiology, University College Cork, Cork, Ireland, APC Microbiome Institute, University College Cork, Cork, Ireland, National Research Council, 100 Sussex Dr, Ottawa, K1A0R6, Canada, Micalis Institute, INRA, AgroParisTech, Universite Paris-Saclay, 78350, Jouy-en-Josas, France University of Littoral Cote d'Opale, convention ANSES, ICV Charles Violette, University of Lille, University of Artois, INRA, ISA, EA 7394, F-62321, Boulogne-sur-mer, France
  Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, 31P NMR, acid hydrolysis, MALDI-TOF MS, ion-exchange chromatography, HF treatment
  
   
  
  Lactococcus lactis ssp. lactis IL1403
  CSDB ID 12812 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: CWP, lipoteichoic acid
Compound class: EPS, cell wall polysaccharide, teichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_1597446,IEDB_983931,SB_192

• Article ID: 487
  Kuebler-Kielb J, Coxon B, Schneerson R "Chemical structure, conjugation, and cross-reactivity of Bacillus pumilus Sh18 cell wall polysaccharide" - Journal of Bacteriology 186(20) (2004) 6891-6901
  

  Bacillus pumilus strain Sh18 cell wall polysaccharide (CWP), cross-reactive with the capsular polysaccharide of Haemophilus influenzae type b, was purified and its chemical structure was elucidated using fast atom bombardment mass spectrometry, nuclear magnetic resonance techniques, and sugar-specific degradation procedures. Two major structures, 1,5-poly(ribitol phosphate) and 1,3-poly(glycerol phosphate), with the latter partially substituted by 2-acetamido-2-deoxy-α-galactopyranose (13%) and 2-acetamido-2-deoxy-α-glucopyranose (6%) on position O-2, were found. A minor component was established to be a polymer of →3-O-(2-acetamido-2-deoxy-β-glucopyranosyl)-1→4-ribitol-1-OPO3→. The ratios of the three components were 56, 34, and 10 mol%, respectively. The Sh18 CWP was covalently bound to carrier proteins, and the immunogenicity of the resulting conjugates was evaluated in mice. Two methods of conjugation were compared: (i) binding of 1-cyano-4-dimethylaminopyridinium tetrafluoroborate-activated hydroxyl groups of the CWP to adipic acid dihydrazide (ADH)-derivatized protein, and (ii) binding of the carbodiimide-activated terminal phosphate group of the CWP to ADH-derivatized protein. The conjugate-induced antibodies reacted in an enzyme-linked immunosorbent assay with the homologous polysaccharide and with a number of other bacterial polysaccharides containing ribitol and glycerol phosphates, including H. influenzae types a and b and strains of Staphylococcus aureus and Staphylococcus epidermidis.

  Haemophilus influenzae, structure, capsular polysaccharide, polysaccharides, antibodies, spectrometry, cell wall, Staphylococcus, conjugate, Bacillus, cross-reactivity, Bacterial Vaccines

  NCBI PubMed ID: 15466043
  Publication DOI: 10.1128/JB.186.20.6891-6901.2004
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: kielbj@mail.nih.gov
  Institutions: Laboratory of Developmental and Molecular Immunity, NIH/NICHD,9000 Rockville Pike, Bldg. 6, Rm. 1A05, Bethesda, MD, USA
  Methods: NMR-2D, FAB-MS, NMR, HF solvolysis, mild acid hydrolysis, Smith degradation
  
   
  
  Streptococcus epidermidis
  CSDB ID 9065 (all data & tools)
• Article ID: 4628
  Valueva OA, Shashkov AS, Zdorovenko EL, Chizhov AO, Kiseleva E, Novik G, Knirel YA "Structures of cell-wall phosphate-containing glycopolymers of Bifidobacterium longum BIM B-476-D" - Carbohydrate Research 373 (2013) 22-27
  

  Glycopolymers with oligosaccharyl phosphate repeats of two types and ribitol and glycerol teichoic acids were isolated from cell wall of Bifidobacterium longum BIM B-476-D by stepwise extraction with 10% CCl3CO2H. The following structures of the glycopolymers were established by sugar analysis, selective cleavage with aq 2% HOAc, dephosphorylation with 48% HF, 2D NMR spectroscopy, and high-resolution ESI MS: [structure: see text]. The ribitol teichoic acid also contains minor D-alanine, whose position was not determined.

  structure, teichoic acid, Bifidobacterium longum, glycopolymers

  NCBI PubMed ID: 23571164
  Publication DOI: 10.1016/j.carres.2013.03.006
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E.L. Zdorovenko
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Belarus, Institute of Microbiology, National Academy of Sciences of Belarus, 220141 Minsk, Belarus
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, NMR-1D
  
   
  
  Bifidobacterium longum BIM B-476-D
  CSDB ID 29779 (all data & tools)
• Article ID: 4819
  Kodali S, Vinogradov E, Lin F, Khoury N, Hao L, Pavliak V, Jones CH, Laverde D, Huebner J, Jansen KU, Anderson AS, Donald RG "A Vaccine Approach for the Prevention of Infections by Multidrug-resistant Enterococcus faecium" - Journal of Biological Chemistry 290(32) (2015) 19512-19526
  

  The incidence of multidrug-resistant Enterococcus faecium hospital infections has been steadily increasing. With the goal of discovering new vaccine antigens, we systematically fractionated and purified four distinct surface carbohydrates from E. faecium endocarditis isolate Tx16, shown previously to be resistant to phagocytosis in the presence of human serum. The two most abundant polysaccharides consist of novel branched heteroglycan repeating units that include signature sugars altruronic acid and legionaminic acid, respectively. A minor high molecular weight polysaccharide component was recognized as the fructose homopolymer levan, and a glucosylated lipoteichoic acid (LTA) was identified in a micellar fraction. The polysaccharides were conjugated to the CRM197 carrier protein, and the resulting glycoconjugates were used to immunize rabbits. Rabbit immune sera were evaluated for their ability to kill Tx16 in opsonophagocytic assays and in a mouse passive protection infection model. Although antibodies raised against levan failed to mediate opsonophagocytic killing, the other glycoconjugates induced effective opsonic antibodies, with the altruronic acid-containing polysaccharide antisera showing the greatest opsonophagocytic assay activity. Antibodies directed against either novel heteroglycan or the LTA reduced bacterial load in mouse liver or kidney tissue. To assess antigen prevalence, we screened a diverse collection of blood isolates (n = 101) with antibodies to the polysaccharides. LTA was detected on the surface of 80% of the strains, and antigens recognized by antibodies to the two major heteroglycans were co-expressed on 63% of these clinical isolates. Collectively, these results represent the first steps toward identifying components of a glycoconjugate vaccine to prevent E. faecium infection.

  antigen, teichoic acid, vaccine, uronic acids, carbohydrate structure, glycoconjugate vaccine, Enterococcus faecium, sialic acids

  NCBI PubMed ID: 26109072
  Publication DOI: 10.1074/jbc.M115.655852
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: robert.donald@pfizer.com
  Institutions: the National Research Council, Ottawa, Ontario K1A 0R6, Canada, the Division of Infectious Diseases, Department of Medicine, University Hospital, Hugstetter Strasse 55, 79106 Freiburg, Germany, and the Department of Pediatrics, Dr. von Hauner Children's Hospital, Ludwig-Maximilians-University, Lindwurmstrasse 4, 80338 Munich, Germany, From Pfizer Vaccine Research and Early Development, Pearl River, New York 10654
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, partial acid hydrolysis, GC-MS, SDS-PAGE, sugar analysis, ELISA, ESI-MS, GC, biological assays, serological methods, UV, HPAEC-PAD, bioinformatic analysis, SEC, conjugatation, SEC-MALLS
  
   
  
  Enterococcus faecium Tx16
  CSDB ID 30963 (all data & tools)
• Article ID: 5832
  Pyclik M, Srutkova D, Schwarzer M, Gorska S "Bifidobacteria cell wall-derived exo-polysaccharides, lipoteichoic acids, peptidoglycans, polar lipids and proteins - their chemical structure and biological attributes" - International Journal of Biological Macromolecules 147 (2020) 333-349
  

  A variety of health benefits has been documented to be associated with the consumption of probiotic bacteria, namely bifidobacteria and lactobacilli. Thanks to the scientific advances in recent years we are beginning to understand the molecular mechanisms by which bacteria in general and probiotic bacteria in particular act as host physiology and immune system modulators. More recently, the focus has shifted from live bacteria towards bacteria-derived defined molecules, so called postbiotics. These molecules may represent safer alternative compared to the live bacteria while retaining the desired effects on the host. The excellent source of effector macromolecules is the bacterial envelope. It contains compounds that are pivotal in the adhesion phenomenon, provide direct bacteria-to-host signaling capacity and the associated physiological impact and immunomodulatory properties of bacteria. Here we comprehensively review the structure and biological role of Bifidobacterium surface and cell wall molecules: exopolysaccharides, cell wall polysaccharides, lipoteichoic acids, polar lipids, peptidoglycans and proteins. We discuss their involvement in direct signaling to the host cells and their described immunomodulatory effects.

  exopolysaccharide, Bacterial antigens, Bifidobacterium, peptidoglycan, lipoteichoic acid, probiotics

  NCBI PubMed ID: 31899242
  Publication DOI: 10.1016/j.ijbiomac.2019.12.227
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: schwarzer@biomed.cas.cz; sabina.gorska@hirszfeld.pl
  Institutions: Laboratory of Microbiome Immunobiology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Laboratory of Gnotobiology, Institute of Microbiology of the Czech Academy of Sciences, Novy Hradek, Czech Republic
  
   
  
  Bifidobacterium longum BIM B-476-D
  CSDB ID 6463 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Compound class: teichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_1597446,IEDB_983931,SB_192

• Article ID: 526
  Sadovskaya I, Vinogradov E, Li J, Jabbouri S "Structural elucidation of the extracellular and cell-wall teichoic acids of Staphylococcus epidermidis RP62A, a reference biofilm-positive strain" - Carbohydrate Research 339(8) (2004) 1467-1473
  

  The ability to adhere to artificial surfaces and form biofilms is considered as a virulence factor of Staphylococcus epidermidis, one of the major causes of nocosomial infections, especially those related to implanted medical devices. Cell-wall teichoic acid is known to play an important role in biofilm formation of staphylococci. The structure of the cell wall and extracellular teichoic acids of S. epidermidis RP62A, a reference biofilm-positive strain, was studied by NMR spectroscopy and capillary electrophoresis-mass spectrometry. Their structures were found to be a (1→3)-linked poly(glycerol phosphate), substituted at the 2-position of glycerol residues with α-Glc, α-GlcNAc, d-Ala and α-Glc6Ala. d-Alanyl acylation of a sugar hydroxyl group seems to be a novel structural feature of teichoic acids from staphylococci

  teichoic acid, Staphylococcus epidermidis, Alanine, Biofilm

  NCBI PubMed ID: 15178389
  Publication DOI: 10.1016/j.carres.2004.03.017
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: jabbouri@univ-littoral.fr
  Institutions: Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Laboratoire de Recherche sur les Biomateriaux et les Biotechnologies, Universite du Littoral-Cote d'Opale, Boulogne-sur-mer, France
  Methods: NMR-2D, NMR, TLC, GLC, MS, GPC
  
   
  
  Staphylococcus epidermidis RP62A
  CSDB ID 9259 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit ; n=45-50
Aglycon: gentiobiosyl-diglyceride
Compound class: lipoteichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_1597446

• Article ID: 1009
  Morath S, Geyer A, Hartung T "Structure-function relationship of cytokine induction by lipoteichoic acid from Staphylococcus aureus" - Journal of Experimental Medicine 193(3) (2001) 393-397
  

  Lipoteichoic acids (LTAs) have been proposed as putative Gram-positive immunostimulatory counterparts to Gram-negative lipopolysaccharides. However, LTA from Staphylococcus aureus, the clinically most frequent Gram-positive pathogen, was inactive after purification. Here, a novel isolation procedure to prepare pure (>99%) biologically active LTA, allowing the first structural analysis by nuclear magnetic resonance and mass spectrometry, is described. A comparison with LTA purified by standard techniques revealed that alanine substituents are lost during standard purification, resulting in attenuated cytokine induction activity. In line with this finding, hydrolysis of alanine substituents of active LTA decimated cytokine induction. LTA represents a major immunostimulatory component of S. aureus.

  Magnetic Resonance Spectroscopy, immunity, Staphylococcus aureus, natural, lipoteichoic acid, tumor necrosis factor, gram-positive bacteria, isolation and purification

  NCBI PubMed ID: 11157059
  Publication DOI: 10.1084/jem.193.3.393
  Journal NLM ID: 2985109R
  Publisher: Rockefeller University Press
  Correspondence: Thomas.Hartung@unikonstanz.de
  Institutions: University of Konstanz, Biochemical Pharmacology, Konstanz, Germany
  Methods: NMR
  
   
  
  Staphylococcus aureus DSM 20233
  CSDB ID 3498 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit ; n=45-50
Aglycon: gentiobiosyl-diglyceride
Compound class: lipoteichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_141807,IEDB_151531,IEDB_1597446

• Article ID: 1009
  Morath S, Geyer A, Hartung T "Structure-function relationship of cytokine induction by lipoteichoic acid from Staphylococcus aureus" - Journal of Experimental Medicine 193(3) (2001) 393-397
  

  Lipoteichoic acids (LTAs) have been proposed as putative Gram-positive immunostimulatory counterparts to Gram-negative lipopolysaccharides. However, LTA from Staphylococcus aureus, the clinically most frequent Gram-positive pathogen, was inactive after purification. Here, a novel isolation procedure to prepare pure (>99%) biologically active LTA, allowing the first structural analysis by nuclear magnetic resonance and mass spectrometry, is described. A comparison with LTA purified by standard techniques revealed that alanine substituents are lost during standard purification, resulting in attenuated cytokine induction activity. In line with this finding, hydrolysis of alanine substituents of active LTA decimated cytokine induction. LTA represents a major immunostimulatory component of S. aureus.

  Magnetic Resonance Spectroscopy, immunity, Staphylococcus aureus, natural, lipoteichoic acid, tumor necrosis factor, gram-positive bacteria, isolation and purification

  NCBI PubMed ID: 11157059
  Publication DOI: 10.1084/jem.193.3.393
  Journal NLM ID: 2985109R
  Publisher: Rockefeller University Press
  Correspondence: Thomas.Hartung@unikonstanz.de
  Institutions: University of Konstanz, Biochemical Pharmacology, Konstanz, Germany
  Methods: NMR
  
   
  
  Staphylococcus aureus DSM 20233
  CSDB ID 3505 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit ; n=45-50
Aglycon: gentiobiosyl-diglyceride
Compound class: lipoteichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_1597446

• Article ID: 1009
  Morath S, Geyer A, Hartung T "Structure-function relationship of cytokine induction by lipoteichoic acid from Staphylococcus aureus" - Journal of Experimental Medicine 193(3) (2001) 393-397
  

  Lipoteichoic acids (LTAs) have been proposed as putative Gram-positive immunostimulatory counterparts to Gram-negative lipopolysaccharides. However, LTA from Staphylococcus aureus, the clinically most frequent Gram-positive pathogen, was inactive after purification. Here, a novel isolation procedure to prepare pure (>99%) biologically active LTA, allowing the first structural analysis by nuclear magnetic resonance and mass spectrometry, is described. A comparison with LTA purified by standard techniques revealed that alanine substituents are lost during standard purification, resulting in attenuated cytokine induction activity. In line with this finding, hydrolysis of alanine substituents of active LTA decimated cytokine induction. LTA represents a major immunostimulatory component of S. aureus.

  Magnetic Resonance Spectroscopy, immunity, Staphylococcus aureus, natural, lipoteichoic acid, tumor necrosis factor, gram-positive bacteria, isolation and purification

  NCBI PubMed ID: 11157059
  Publication DOI: 10.1084/jem.193.3.393
  Journal NLM ID: 2985109R
  Publisher: Rockefeller University Press
  Correspondence: Thomas.Hartung@unikonstanz.de
  Institutions: University of Konstanz, Biochemical Pharmacology, Konstanz, Germany
  Methods: NMR
  
   
  
  Staphylococcus aureus DSM 20233
  CSDB ID 3506 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: teichoic acid, lipoteichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_1597446

• Article ID: 1176
  Schipper D "Structural studies of the teichoic acids from Bacillus licheniformis" - Carbohydrate Research 279(1) (1995) 75-82
  

  structural, acid, phosphate, structural studies, teichoic acids, teichoic acid, Bacillus, glycerol, Bacillus licheniformis

  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of NMR and IR Spectroscopy, Delft, The Netherlands
  Methods: NMR
  
   
  
  Bacillus licheniformis
  CSDB ID 4617 (all data & tools)
• Article ID: 1219
  Shashkov AS, Potekhina NV, Naumova IB, Evtushenko LI, Widmalm G "Cell wall teichoic acid of Actinomadura viridis VKM Ac-1315T" - European Journal of Biochemistry 262 (1999) 688-695
  

  structure, cell, acid, phosphate, cell wall, teichoic acid, glycerol, Actinomadura, actinomycete, madurose

  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: Shash@ioc.ac.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: NMR
  
   
  
  Actinomadura viridis VKM Ac-1315T
  CSDB ID 4771 (all data & tools)
• Article ID: 1634
  Morath S, von AS, Hartung T "Structure/function relationships of lipoteichoic acids" - Journal of Endotoxin Research 11(6) (2005) 348-356
  

  The role of lipoteichoic acids (LTAs) from Gram-positive bacteria as immunostimulatory molecules was controversial for many years, as inadequate preparation methods as well as heterogeneous and endotoxin-contaminated commercial preparations led to conflicting results. An improved purification methodology for LTA now yields potent bioactive and chemically defined material, which is currently being characterized in various models. A synthetic analogue of Staphylococcus aureus LTA has proven the structure/function relationship. The key role of D-alanine esters for the immune response of LTA was confirmed by synthetic derivatives. The glycolipid anchor of LTA plays a central role analogous to the lipid A of LPS. Methodological aspects and criteria for quality assessment of LTA preparations are discussed.

  purification, lipoteichoic acid, structural identification, structure/function relationship

  NCBI PubMed ID: 16303090
  Publication DOI: 10.1179/096805105X67328
  Journal NLM ID: 9433350
  Publisher: Maney Publishing
  Institutions: Department of Biochemical Pharmacology, University of Konstanz, Konstanz, Germany, European Center for the Validation of Alternative Methods (ECVAM), Joint Research Center, Ispra, Italy
  Methods: NMR
  
   
  
  Staphylococcus aureus DSM 20233
  CSDB ID 10740 (all data & tools)
• Article ID: 1639
  Potekhina NV, Shashkov AS, Streshinskaya GM, Senchenkova SN, Evtushenko LI "Anionic Polymers of the Cell Wall of Brevibacterium linens VKM Ac-2159" - Biochemistry (Moscow) 70(9) (2005) 1046-1054
  

  Unsubstituted 1,3-poly(glycerol phosphate) and two sugar-1-phosphate polymers were identified in the cell wall of Brevibacterium linens VKM Ac-2159 by NMR spectroscopy and chemical methods. A monomer of one of the sugar-1-phosphate polymers has the branched repeating unit of the following structure: -4)-[β-D-GlcpNAc-(1→3)]-α-D-Glcp-(1-P-. The repeating unit of another sugar-1-phosphate polymer has a linear structure consisting of alternating β- and α-N-acetylglucosamine residues: -4)-β-D-GlcpNAc-(1→6)-α-D-GlcpNAc-(1-P-. Some part of the β-N-acetylglucosaminyl residues bear O-ester-bound succinic acid residues at C-3. The identified sugar-1-phosphate polymers have not been described earlier in cell walls of other bacteria.

  structure, cell, chain, polymer, acid, phosphate, bacteria, cell wall, biochemistry, teichoic acids, pyruvic acid, biology, component, galactose, time, teichoic acid, Polymers, Gram-positive, PDF, Acids, glycerol, configuration, absolute configuration, gram-positive bacteria, Brevibacterium, mannitol, anionic, D-mannitol

  NCBI PubMed ID: 16266278
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: potekchina@hotbox.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Faculty of Biology, Lomonosov Moscow State University, 119992 Moscow, Russia, fax: (7-095) 939-4309, fax: (7-095) 135-5328, All-Russian Collection of Microorganisms (VKM), Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia, fax: (7-095) 923-3602
  Methods: NMR, composition analysis
  
   
  
  Brevibacterium linens VKM Ac-2159
  CSDB ID 10748 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130648,IEDB_130695,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_153207,IEDB_1597446,IEDB_885822,IEDB_983931,SB_192

• Article ID: 1217
  Shashkov AS, Tul'skaya EM, Grachev AA, Evtushenko LI, Bueva OV, Naumova IB "Structure of cell-wall teichoic acid of Streptomyces sparsogenes VKM Ac-1744T" - Biochemistry (Moscow) 63 (1998)
  

  structure, cell, polymer, acidic, acid, bacteria, cell wall, 13C NMR, function, teichoic acid, Streptomyces, Gram-positive, anionic, taxonomy

  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Institute of biochemistry and Physiology of Microorganisms,Russian Academy of Sciences,Pushchino,Russia
  Methods: NMR
  
   
  
  Streptomyces sparsogenes VKM Ac-1744T
  CSDB ID 4710 (all data & tools)