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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

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

Information on the prevalence, compositions, and structures of anionic carbohydrate-containing polymers of cell walls of Gram-positive bacteria is summarized. The data suggest that these polymers are important for normal functioning of bacterial cells and require further studies. Structural data on teichoic acids found in the literature published over the last few years are discussed. This is a very diverse class of polymers whose structure-specific pathways of degradation were studied and NMR spectra were examined. Unique comprehensive tables of 13C-NMR spectroscopic data (mainly obtained by the authors) on these polymers are given in the Appendix. Other tables summarize data on teichuronic acids, sugar-phosphate polymers, acid polysaccharides, and structural variants of bonds between acid polysaccharides and peptidoglycans known from the literature. Functions of anionic polymers and their possible chemotaxonomic applications are discussed

13C-NMR, NMR, structure, cell wall, composition, teichoic acid, teichuronic acid, Gram-positive, gram-positive bacteria, taxonomy

NCBI PubMed ID: 9360295
Journal NLM ID: 0376536
Publisher: Nauka/Interperiodica
Institutions: School of Biology, Lomonosov Moscow State University, Russia

Two different teichoic acids, along with a teichulosonic and a teichuronic acids, were identified in the cell wall of Brevibacterium aurantiacum VKM Ac-2111(Т). One teichoic acid is 1,3-poly(glycerol phosphate) with 2-acetamido-2-deoxy-α-D-galactopyranose and L-glutamic acid as non-stoichiometric substituents at O-2 of the glycerol residue. The second one is a poly(glycosylglycerol phosphate) with -4)-α-D-Galp-(1→2)-sn-Gro-(3-P- and/or -6)-α-D-Galp-(1→2)-sn-Gro-(3-P- units in the main chain. The structure of the first has not been reported so far, while the latter one is new for actinobacteria. The teichulosonic acid with α-3-deoxy-β-D-glycero-D-galacto-non-2-ulopyranosonic acid (Kdn) and β-D-glucopyranose residues in the backbone represents a novel polymer: →8)-α-Kdn-(2→6)-β-D-Glcp-(1→. The teichuronic acid has also hitherto unknown structure: → 3)-β-D-Galf(2OAc)0.3-(1→3)-β-D-GlcpА-(1→ and is found in members of the genus Brevibacterium for the first time. The polymer structures were elucidated using 1D- and 2D-NMR spectroscopy: (1)H,(1)H COSY, TOCSY, ROESY, (1)H,(13)C HSQC, HSQC-TOCSY, and (1)H,(13)C and (1)H,(31)P HMBC.

teichoic acid, teichuronic acid, Kdn, Brevibacterium, Glutamic Acid, teichulosonic acid

NCBI PubMed ID: 26765252
Publication DOI: 10.1016/j.carres.2015.12.007
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: potekhina56@mail.ru
Institutions: School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, Russian Federation, All-Russian Collection of Microorganisms (VKM), G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, paper chromatography, NMR-1D, paper electrophoresis