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PubMed2004

Cell wall teichoic acids of two Brevibacterium strains.

Structurally identical teichoic acids were detected in cell walls of two soil isolates assigned to Brevibacterium linens based on phylogenetic data. Both cell walls contain unsubstituted 1,3-poly(glycerol phosphate) and poly(glycosylglycerol phosphate). Repeating units of the latter--alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->1)-Gro--are bound by phosphodiester bonds including OH-3 of galactose and OH-3 of glycerol. Some of the N-acetylglucosamine residues have 4,6-pyruvic acid acetal, amounts of the latter in the two strains being unequal. Species-specificity of the structures of teichoic acids in the genus Brevibacterium is discussed.

Brevibacterium↗
PubMedDate not supplied

[Cell wall teichoic acids from Streptomyces daghestanicus VKM Ac-1722T and Streptomyces murinus INA-00524T].

The structure of cell wall teichoic acids was studied by chemical methods and NMR spectroscopy in the type strains of two actinomycete species of the "Streptomyces griseoviridis" phenetic cluster: Streptomyces daghestanicus and Streptomyces murinus. S. daghestanicus VKM Ac-1722T contained two polymers having a 1,5-poly(ribitol phosphate) structure. In one of them, the ribitol units had alpha-rhamnopyranose and 3-O-methyl-alpha-rhamnopyranose substituents; in the other, each ribitol unit was carrying 2,4-ketal-bound pyruvic acid. Such polymers were earlier found in the cell walls of Streptomyces roseolus and Nocardiopsis albus, respectively; however, their simultaneous presence in the cell wall has never been reported. The cell wall teichoic acid of Streptomyces murinus INA-00524T was is a 1,5-poly(glucosylpolyol phosphate), whose repeating unit was [-6)-beta-D-glucopyranosyl-(1 --> 2)-glycerol phosphate-(3-P-]. Such a teichoic acid was earlier found in Spirilliplanes yamanashiensis. The 13C NMR spectrum of this polymer is presented for the first time. The results of the present investigation, together with earlier published data, show that the type strains of four species of the "Streptomyces griseoviridis" phenetic cluster differ in the composition and structure of their teichoic acids; thus, teichoic acids may serve as chemotaxonomic markers of the species.

Cell Wall↗
PubMed1978

Further evidence for the structure of the teichoic acids from Bacillus stearothermophilus B65 and Bacillus subtilis var. niger WM.

Bacillus stearothermophilus B65 and Bacillus subtilis var. niger WM both contain teichoic acids in their walls composed of glycerol, phosphate and glucose. The 13C nuclear magnetic resonance spectrum of B. stearothermophilus teichoic acid showed 13C-31P coupling on the signals from the C-5 and C-6 carbon atoms of the glucose molecule and an alpha-glucosidic linkage between glucose and the C-1 atom of the glycerol moiety. These data are consistent with a poly[glucosylglycerol phosphate] as the cell-wall teichoic acid in this organism. B. subtilis var. niger WM teichoic acid was oxidized by periodate and incubated in glycine buffer at pH 10.5. This treatment did not significantly increase the phosphomonoester content (by beta-elimination of the phosphate groups) of the teichoic acid molecule (7.1 to 9.5%), which is in accordance with earlier data derived from 13C nuclear magnetic resonance spectroscopy [De Boer et al. (1976) Eur. J. Biochem. 62, 1-6], that in this organism the glucose is not an integral part of the polymer chain. Similar treatment of B. stearothermophilus B65 teichoic acid increased the phosphomonoester content of the preparation from 0.15 to 68.1%.

Bacillus subtilis↗
PubMed2002

A polymer with a backbone of 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid, a teichuronic acid, and a beta-glucosylated ribitol teichoic acid in the cell wall of plant pathogenic Streptomyces sp. VKM Ac-2124.

Structures of cell wall anionic polymers of the strain Streptomyces sp. VKM Ac-2124, a causative agent of potato scab, which is phylogenetically the closest to plant pathogenic species S. setonii and S. caviscabies, were studied. The strain contains three anionic glycopolymers, viz., a teichuronic acid with a disaccharide repeating unit -->6)-alpha-d-Glcp-(1-->4)-beta-d-ManpNAc3NAcA-(1-->, a beta-glucosylated polymer of 3-deoxy-d-glycero-d-galacto-non-2-ulopyranosonic acid (Kdn), and a beta-glucosylated 1,5-poly(ribitol phosphate). The strain studied is the second representative of plant pathogenic streptomycetes inducing potato scab disease, the cell wall anionic polymers of which were shown to contain a Kdn-polymer. Presumably, the presence of Kdn-containing structures in the surface regions of pathogens is essential for their efficient attachment to host plant cells.

Cell Wall↗
PubMed1973

Teichoic acid of a stabilized L-form of Streptococcus pyogenes.

A stabilized L-form of Streptococcus pyogenes continues to synthesize glycerol teichoic acid. This polymer was obtained from S. pyogenes and its L-form, treated in identical fashion, and compared. Highly purified glycerol teichoic acid from only the L-form was found to be devoid of d-alanine and to have a shorter chain length. Otherwise, the glycerol teichoic acid from these two organisms was found to be a 1,3-phosphodiester-linked glycerophosphate polymer substituted with d-glucose. Evidence is presented that most, if not all, of the glycerol teichoic acid in this streptococcus lies between the wall and membrane. A possible need for the continued synthesis of a minute amount of glycerol teichoic acid by this L-form for survival is discussed in terms of the known function of teichoic acids in bacteria.

Alanine↗
PubMed1975

Glycerol teichoic acid as an antigenic determinant in a Gram-negative bacterium Butyrivibrio fibrisolvens.

An antigenic determinant isolated from a strain of the Gram-negative bacterium Butyrivibrio fibrisolvens reacted with specific antisera to the polyglycerophosphate backbone of membrane teichoic acids of lactobacilli. It gave a reaction of identity with membrane glycerol lipoteichoic acid and glycerol teichoic acid preparations from lactobacilli, and with phenol extracts of other Gram-positive bacteria. The antigen-antibody reactions was strongly inhibited by glycerol-phosphoryl-glycerol-phosphoryl-glycerol and the chemical composition was consistent with glycerol teichoic acid. It was concluded that this Gram-negative bacterium contained a glycerol teichoic acid whose polyglycerophospate backbone was acting as antigenic determinant. Extracts of 33 out of 52 other strains of butyrivibrios examined gave similar reactions.

Antibodies, Bacterial↗
PubMed1985

Characteristics of the binding of aminoglycoside antibiotics to teichoic acids. A potential model system for interaction of aminoglycosides with polyanions.

The binding of the aminoglycoside antibiotic dihydrostreptomycin to defined cell-wall teichoic acids and to lipoteichoic acid isolated from various gram-positive eubacteria was followed by equilibrium dialysis. Dihydrostreptomycin was used at a wide range of concentration under different conditions of ionic strength, concentration of teichoic acid, presence of cationic molecules like Mg2+, spermidine, other aminoglycoside antibiotics (gentamicin, neomycin, paromomycin). Interaction of dihydrostreptomycin with teichoic acid was found to be a cooperative binding process. The binding characteristics seem to be dependent on structural features of teichoic acid and are influenced by cationic molecules. Mg2+, spermidine and other aminoglycosides antibiotics inhibit the binding of dihydrostreptomycin to teichoic acid competitively. The binding of aminoglycosides to teichoic acids is considered as a model system for the interaction of aminoglycoside antibiotics with cellular polyanions. Conclusions of physiological significance are drawn.

Aminoglycosides↗
PubMed1985

Enzyme immunoassay of teichoic acids from Listeria monocytogenes.

Amino groups were introduced into Listeria monocytogenes teichoic acids by reductive amination, and the product was coupled to biotin. Teichoic acids were assayed by their binding to specific antibody adsorbed to a solid phase, followed by detection of the antigen-antibody complex by horseradish peroxidase-avidin. Less than 20 ng of teichoic acid was detectable.

Antibodies, Bacterial↗
PubMed2006

Structural elucidation of the extracellular and cell-wall teichoic acids of Staphylococcus aureus MN8m, a biofilm forming strain.

Extracellular teichoic acid, an essential constituent of the biofilm produced by Staphylococcus epidermidis strain RP62A, is also an important constituent of the extracellular matrix of another biofilm producing strain, Staphylococcus aureus MN8m. The structure of the extracellular and cell wall teichoic acids of the latter strain was studied by NMR spectroscopy and capillary electrophoresis-mass spectrometry. Both teichoic acids were found to be a mixture of two polymers, a (1-->5)-linked poly(ribitol phosphate), substituted at the 4-position of ribitol residues with beta-GlcNAc, and a (1-->3)-linked poly(glycerol phosphate), partially substituted with the D-Ala at 2-position of glycerol residue. Such mixture is unusual for S. aureus.

Biofilms↗
PubMed2006

Wall teichoic acid polymers are dispensable for cell viability in Bacillus subtilis.

An extensive literature has established that the synthesis of wall teichoic acid in Bacillus subtilis is essential for cell viability. Paradoxically, we have recently shown that wall teichoic acid biogenesis is dispensable in Staphylococcus aureus (M. A. D'Elia, M. P. Pereira, Y. S. Chung, W. Zhao, A. Chau, T. J. Kenney, M. C. Sulavik, T. A. Black, and E. D. Brown, J. Bacteriol. 188:4183-4189, 2006). A complex pattern of teichoic acid gene dispensability was seen in S. aureus where the first gene (tarO) was dispensable and later acting genes showed an indispensable phenotype. Here we show, for the first time, that wall teichoic acid synthesis is also dispensable in B. subtilis and that a similar gene dispensability pattern is seen where later acting enzymes display an essential phenotype, while the gene tagO, whose product catalyzes the first step in the pathway, could be deleted to yield viable mutants devoid of teichoic acid in the cell wall.

Bacillus subtilis↗
PubMed1999

Transposon-induced mutations in two loci of Listeria monocytogenes serotype 1/2a result in phage resistance and lack of N-acetylglucosamine in the teichoic acid of the cell wall.

Teichoic acid-associated N-acetylglucosamine and rhamnose have been shown to serve as phage receptors in Listeria monocytogenes serotype 1/2a. We generated and characterized two single-copy Tn916DeltaE mutants which were resistant to phage A118 and several other serotype 1/2a-specific phages. In one mutant the insertion was immediately upstream of the recently identified ptsHI locus, which encodes two proteins of the phosphoenolpyruvate-dependent carbohydrate uptake system, whereas in the other the insertion was immediately upstream of an operon whose most distal gene was clpC, involved in stress responses and virulence. Transduction experiments confirmed the association of the phage-resistant phenotype of these mutants with the transposon insertion. Phage A118 resistance of the mutants could be attributed to inability of the phage to adsorb onto the mutant cells, and biochemical analysis of cell wall composition showed that the teichoic acids of both mutants were deficient in N-acetylglucosamine. Rhamnose and other teichoic acid and cell wall components were not affected.

Acetylglucosamine↗
PubMed2004

Structures of cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106.

Structures of two cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106 were studied. The structure of mannitol teichoic acid described earlier was mainly confirmed. This polymer is 1,6-poly(mannitol phosphate) bearing beta-D-glucopyranosyl residues at the C-2 of mannitol and pyruvic acid residues at the C-4 and C-5. The absolute configurations of D-mannitol and S-pyruvic acid were found. The following distinctions from the earlier described structure were found: unsubstituted 1,6-poly(mannitol phosphate) residues and residues substituted only by beta-D-glucopyranosyl at the C-2 of mannitol but unsubstituted by pyruvic acid are present in the chain. The structure of glycerol teichoic acid present in the cell wall as a minor component (approximately 7%) is also described. This acid is identified as 1,3-poly(glycerol phosphate) substituted at the C-2 of glycerol by 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residues bearing R-pyruvic acid residues at the C-4 and C-6 of galactose. This polymer is for the first time described in the cell wall of Gram-positive bacteria.

Brevibacterium↗
PubMed1985

A common linkage saccharide unit between teichoic acids and peptidoglycan in cell walls of Bacillus coagulans.

Teichoic acid-glycopeptide complexes were isolated from lysozyme digests of the cell walls of Bacillus coagulans AHU 1631, AHU 1634, and AHU 1638, and the structure of the teichoic acid moieties and their linkage regions was studied. On treatment with hydrogen fluoride, each of the complexes gave a hexosamine-containing disaccharide, which was identified to be glucosyl(beta 1----4)N-acetylglucosamine, in addition to dephosphorylated repeating units of the teichoic acids, namely, galactosyl(alpha 1----2)glycerol and either galactosyl(alpha 1----2)[glucosyl(alpha 1----1/3)]glycerol (AHU 1638) or galactosyl(alpha 1----2)[glucosyl(beta 1----1/3)]glycerol (AHU 1631 and AHU 1634). From the results of Smith degradation, methylation analysis, and partial acid hydrolysis, the teichoic acids from these strains seem to have the same backbone chains composed of galactosyl(alpha 1----2)glycerol phosphate units joined by phosphodiester bonds at C-6 of the galactose residues. The presence of the disaccharide, glucosyl(beta 1----4)N-acetylglucosamine, in the linkage regions between teichoic acids and peptidoglycan was confirmed by the isolation of a disaccharide-linked glycopeptide fragment from each complex after treatment with mild alkali and of a teichoic acid-linked saccharide from each cell wall preparation after treatment with mild acid. Thus, it is concluded that despite structural differences in the glycosidic branches, the teichoic acids in the cell walls of the three strains are linked to peptidoglycan through a common linkage saccharide, glucosyl (beta 1----4) N-acetylglucosamine.

Bacillus↗
PubMedDate not supplied

Comparison of cell wall teichoic acid fractions isolated from three different encapsulated strains of Staphylococcus epidermidis.

Teichoic acid preparations extracted from the cell wall of three serologically different encapsulated strains of Staphylococcus epidermidis, ATCC-31432 (capsular type I), SE-360 (capsular type II) and SE-10 (capsular type III) were purified by DEAE-cellulose and Sephadex G-50 column chromatography. The preparations showed immunological heterogeneity by an agar diffusion test. The chemical properties of the cell wall teichoic acid preparations of capsular types I and III were regarded as N-acetyl-glucosaminyl glycerol-phosphate polymers containing N-acetylglucosamine and phosphate at molar ratios of 0.22-1.0 and 0.33-1.0, respectively. The preparation of capsular type II was assumed to be an alpha-glucosyl glycerol-phosphate polymer containing glucose and phosphate at a molar ratio of 0.49-1.0, and it reacted strongly with concanavalin A. Moreover, alanine, glycine, serine and lysine were shown, among these preparations, to be a common amino acid composition. These results indicate that cell wall teichoic acids obtained from these strains were biochemically and immunologically different from each other.

Cell Wall↗
PubMed1992

Location of peptidoglycan and teichoic acid on the cell wall surface of Staphylococcus aureus as determined by immunoelectron microscopy.

Anti-peptidoglycan (PG) and anti-teichoic acid (TA) antibodies were prepared from sera of rabbits immunized with the cell wall fraction of Staphylococcus aureus Cowan I by the specific adsorption technique with purified teichoic acid or peptidoglycan. The anti-PG antibody recognized the trichloroacetic acid-treated walls (TCA wall) prepared from S. aureus, Bacillus subtilis, and Micrococcus luteus but did not react with teichoic acid or proteins extracted from the cell wall of Staphylococcus. The anti-TA antibody specifically reacted with cell wall teichoic acid of beta-type sugar configuration. The reaction sites of these antibodies on the cell wall of S. aureus Wood 46 were determined by immunoelectron microscopy using colloidal gold as a probe. The anti-TA antibody reacted mostly with the fibrous electron-dense mass on the cell surface. The reaction was also seen on the inner surface of the cell wall. The anti-PG antibody reacted with the fibrous structures and also directly on the cell wall surface. The distribution of the probes on the cell wall surface examined with the scanning electron microscope showed that there was no localized distribution in respect to the cell division. We knew from these observations that the external surface of the cell wall of Staphylococcus is covered with the fibrous mass which consists mostly of teichoic acid but partially of peptidoglycan.

Antibodies, Bacterial↗
PubMedDate not supplied

[Ratio of glycan to teichoic acid in Actinomyces thermovulgaris cell wall].

The molar ratio between glycan and teichoic acid was studied in the cell wall of Actinomyces thermovulgaris. A chain of teichoic acid consisting of 13 glycerophosphate units was found to correspond to 6--7 disaccharide units of glycan. The cell wall contains 31% of the glycan of the glycopeptide and 25% of teichoic acid. The content of glycan was calculated using the concentration of muramic acid in the wall. The cell wall was found to contain 1.02% of O-acetyl groups.

Actinomyces↗
PubMed2002

Cell wall teichoic acids of actinomycetes of three genera of the order actinomycetales.

The structures of cell wall teichoic acids of the members of newly recognized genera of the order Actinomycetales were studied. Planotetraspora mira VKM Ac-2000T contains two types of teichoic acids: 2,3-poly(glycerol phosphate) substituted with alpha-D-Galp at C-1 of glycerol and 1,3-poly(glycerol phosphate) substituted with alpha-L-Rhap at OH-2 of glycerol (60%). Herbidospora cretacea VKM Ac-1997T contains the chains of 1,3-poly(glycerol phosphate) partially substituted with alpha-D-Galp and alpha-D-GalpNAc at C-2 of glycerol. The majority of alpha-D-galactopyranosyl residues are substituted at OH-3 with a sulfate. The aforementioned teichoic acids have not been found in bacteria thus far. Actinocorallia herbida VKM Ac-1994T contains poly(galactosylglycerol phosphate), with the beta-Galp-(1-->2)-Gro-P repeating units being linked via the phosphodiester bonds between the OH-3 of glycerol and OH-6 of galactose. Earlier, this structure was found in the cell wall of Actinomadura madura. The polymer structures were determined by chemical analysis and using 13C-NMR spectroscopy. The results show that teichoic acids are widespread in the order Actinomycetales.

Actinomycetales↗
PubMed1986

Antibodies to staphylococcal teichoic acid and alpha toxin in patients with cystic fibrosis.

Enzyme-linked immunosorbent assay (ELISA) was used for IgG antibody determination to teichoic acid and alpha-toxin from Staphylococcus aureus in 65 patients with cystic fibrosis (CF). In patients chronically colonized with S. aureus, elevated titres to teichoic acid were found in 13/35 (37%) patients, to alpha-toxin in 12/35 (34%) and to either antigen in 18/35 (51%). Patients with elevated titres to teichoic acid had a significantly lower X-ray score than patients with normal titres. The highest titres against both teichoic acid and alpha-toxin were seen in patients not receiving optimal treatment. These findings suggest that staphylococci contribute to the tissue damage in CF and that the determination of antibodies especially to staphylococcal teichoic acid might be of value in the diagnosis and management of staphylococcal infections in patients with CF.

Adolescent↗