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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl 1-phosphate)
Compound class: cell wall polysaccharide, teichoic acid

• Article ID: 3146
  Kozlova YI, Streshinskaya GM, Shashkov AS, Senchenkova SN, Evtushenko LI "Carbohydrate-containing polymers of the cell wall of the thermophilic streptomycete Streptomyces thermoviolaceus subsp. thermoviolaceus VKM Ac-1857T" - Biochemistry (Moscow) 71(7) (2006) 775-780
  

  Anionic polymers of the cell surface of a thermophilic streptomycete were investigated. The cell wall of Streptomyces thermoviolaceus subsp. thermoviolaceus VKM Ac-1857(T) was found to contain polymers with different structure: teichoic acid - 1,3-poly(glycerol phosphate), disaccharide-1-phosphate polymer with repeating unit -6)-α-Galp-(1→6)-α-GlcpNAc-P-, and polysaccharide without phosphate with repeating unit →6)-α-GalpNAc-(1→3)-β-GalpNAc-(1→. Disaccharide-1-phosphate and polysaccharide without phosphate have not been described earlier in prokaryotic cell walls

  structure, polysaccharide, repeating unit, cell wall, translation, surface, teichoic acid, Streptomyces

  NCBI PubMed ID: 16903832
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: streshinskaya@mail.ru
  Institutions: Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia, Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia.
  Methods: NMR, sugar analysis
  
   
  
  Streptomyces thermoviolaceus ssp. thermoviolaceus VKM Ac-1857 (T)
  CSDB ID 20027 (all data & tools)
• Article ID: 3159
  Shashkov AS, Streshinskaya GM, Senchenkova SN, Kozlova YI, Alferova IV, Terekhova LP, Evtushenko LI "Cell wall teichoic acids of streptomycetes of the phenetic cluster 'Streptomyces fulvissimus'" - Carbohydrate Research 341(6) (2006) 796-802
  

  Structures of the anionic polymers of streptomycetes Streptomyces fulvissimus VKM Ac-994(T), Streptomyces longispororuber VKM Ac-1735(T), Streptomyces aureoveticillatus VKM Ac-48(T) and Streptomyces spectabilis INA 00606 belonging to the phenetic cluster 'S. fulvissimus' were investigated by chemical and NMR spectroscopic methods. A teichoic acid from the cell wall of S. spectabilis INA 00606 was studied in more detail, and this was shown to represent 1,3-poly(glycerol phosphate) substituted with glucosamine (α-D-GlcNAc) and l-glutamic acid (non-stoichiometric substitution). For the first time, glutamic acid is identified as an acyl substituent in teichoic acids of streptomycetes. The polymer chain is built of the following fragments: Cell walls of other streptomycetes of the phenocluster under study contain 1,3-poly(glycerol phosphates) with glucosamine as a glycosyl substituent at O-2 of the glycerol phosphate units and l-glutamic acid and lysine as O-2 acyl substituents. Not all amino sugar residues in the polymers of these strains are N-acetylated, and the content of the glucosamine and lysine residues in the polymers of different strains is not the same. Despite certain quantitative differences in the structures of the polymers, one may consider streptomycetes of the phenocluster 'S. fulvissimus' as closely related microorganisms, the details of the structures serving as additional criteria for the determination of the species status of a strain under study

  NMR, structure, chemistry, strain, cell, chain, polymer, determination, acid, phosphate, cluster, cell wall, chemical, sugar, method, teichoic acids, difference, fragment, content, methods, time, amino, glycosyl, teichoic acid, species, quantitative, Polymers, Streptomyces, PDF, organic, Acids, Glucosamine, amino sugar, glycerol, substitution, lysine, anionic, acyl, D, Glutamic Acid, L-glutamic acid, Phosphates

  NCBI PubMed ID: 16458865
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, chemical methods
  
   
  
  Streptomyces fulvissimus VKM Ac-994t, Streptomyces spectabilis INA 00606
  CSDB ID 20132 (all data & tools)
• Article ID: 3253
  Leone S, Molinaro A, Romano I, Nicolaus B, Lanzetta R, Parrilli M, Holst O "The structures of the cell wall teichoic acids from the thermophilic microorganism Geobacillus thermoleovorans strain Fango" - Carbohydrate Research 341(15) (2006) 2613-2618
  

  The structures of two teichoic acid fractions (TA1 and TA2) isolated from the thermophilic gram-positive bacterium Geobacillus thermoleovorans strain Fango were investigated by means of chemical and NMR spectroscopic methods. The most abundant species (TA1) exhibited a rather regular structure comprising two different repeating units of 1,3-glycerol phosphate nonstoichiometrically substituted by terminal-α-D-Galp (t-α-D-Galp). The second molecular species (TA2) presented a higher structural variability and t-α-D-Glcp and the disaccharides t-α-D-GlcpNAc-(1→2)-α-D-Glcp and t-α-D-GlcpNAc-(1→3)-α-D-Glcp were also present as minor substituents at O-2 of the glycerol phosphate residues. Minor substitution by alanine could also be detected.

  NMR spectroscopy, teichoic acids, Bacterial cell wall, Geobacillus thermoleovorans

  NCBI PubMed ID: 16930569
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: molinaro@unina.it
  Institutions: Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, D-23845 Borstel, Germany, Dipartimento di Chimica Organica e Biochimica, Universita degli Studi di Napoli Federico II, Via Cintia, 4 I-80126 Napoli, Italy, Istituto di Chimica Biomolecolare (ICB-CNR), via Campi Flegrei 34, 80078 Pozzuoli, Napoli, Italy
  Methods: NMR, sugar analysis
  
   
  
  Geobacillus thermoleovorans Fango
  CSDB ID 20097 (all data & tools)
• Article ID: 3766
  Potekhina NV, Streshinskaia GM, Kozlova YI, Kudryashova EB, Senchenkova SN, Shashkov AS, Anan'nia LN "Heterogeneous set of cell wall teichoic acids in strains of Bacillus subtilis VKM B-760 and VKM B-764" - Biochemistry 74(12) (2009) 1368-1374
  

  Cell walls of Bacillus subtilis VKM B-760 and VKM B-764 are characterized by heterogeneous composition of teichoic acids. Polymer I with structure -6)-β-D-Galp-(1→1)-sn-Gro-(3-P-, polymer II with structure -6)-α-D-Glcp-(1→1)-sn-Gro-(3-P-, and a small amount of unsubstituted 1,3-poly(glycerol phosphate) were detected in strain VKM B-760. Strain VKM B-764 contains an analogous set of teichoic acids, but a characteristic feature of polymer II is the presence of disubstituted glycerol residue with α-glucopyranose localization in the integral chain at C-1 hydroxyl and β-glucopyranose as a side branch at C-2 hydroxyl (polymer III): -6)-α-D-Glcp-(1→1)-[β-D-Glcp-(1→2)]-sn-Gro-(3-P-. The structures of polymer I in bacilli and polymer III in Gram-positive bacteria are described for the first time. Teichoic acids were studied by chemical methods and on the basis of combined analysis of one-dimensional 1H-, 13C-, and (31)P-NMR spectra, homonuclear two-dimensional (1)H/(1)H COSY, TOCSY, and ROESY, and heteronuclear two-dimensional (1)H/(13)C gHSQC- and HMQC-TOCSY experiments. Simultaneous presence of several different structure teichoic acids in the bacillus cell walls as well as chemotaxonomical perspectives of the application of these polymers as species-specific markers for members of the Bacillus genus is discussed.

  NMR spectroscopy, cell wall, teichoic acids, Bacillus subtilis

  NCBI PubMed ID: 19961419
  Publication DOI: 10.1134/S0006297909120116
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: potekchina@hotbox.ru
  Institutions: Faculty of Biology, Lomonosov Moscow State University, Moscow, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, NMR-1D, genetic methods, acid degradation
  
   
  
  Bacillus subtilis VKM B-760
  CSDB ID 24187 (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 24289 (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 licheniformis, Bacillus pumilus AHU 1650
  CSDB ID 26320 (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 VKM B-760, Bacillus subtilis VKM B-764
  CSDB ID 26489 (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 licheniformis VKM B-511T, Bacillus pumilus VKM B-508T, Bacillus pumilus VKM B-424, Bacillus pumilus VKM B-711, Bacillus subtilis ssp. subtilis VKM B-501
  CSDB ID 27327 (all data & tools)
• Article ID: 4443
  Dmitrieva NF, Naumova IB, Streshinskaya GM, Panina LI "On the cell wall of Actinomyces rimosus LCT-118" - Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 2(6) (1976) 815-821
  

  The structure of the teichoic acid from the cell wall of Act. rimous LCT-118 producing the antibiotic oxytetracycline is stuted. The polymer consists of 10 glycerol units linked in phosphodiester bonds of 1,3-type. Three O-acetyl groups are attached to the polymer through ester linkades. It is established that one chain of teichoic acid corresponds to 20 units of muramic acid of glycopeptide. The cell wall contains 2.3% (of dry weight) O-acetyl groups which are bound with techoic acids and some other compounds. The estimation of aminosugars content is based on the estimation of N-acetyl groups.

  structure, cell wall, teichoic acid, Actinomyces

  Journal NLM ID: 7804941
  Publisher: Moskva: Nauka
  Institutions: M.V. Lomonosov State University, Moscow
  Methods: gel filtration, sugar analysis, paper chromatography, electrophoresis, alkaline hydrolysis, acid degradation
  
   
  
  Actinomyces rimosus LCT-118
  CSDB ID 29001 (all data & tools)