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PubMed1976

In vitro synthesis of the unit that links teichoic acid to peptidoglycan.

The role of cytidine diphosphate (CDP)-glycerol in gram-positive bacteria whose walls lack poly(glycerol phosphate) was investigated. Membrane preparations from Staphylococcus aureus H, Bacillus subtilis W23, and Micrococcus sp. 2102 catalyzed the incorporation of glycerol phosphate residues from radioactive CDP-glycerol into a water-soluble polymer. In toluenized cells of Micrococcus sp. 2102, some of this product became linked to the wall. In each case, maximum incorporation of glycerol phosphate residues required the presence of the nucleotide precursors of wall teichoic acid and of uridine diphosphate-N-acetylglucosamine. In membrane preparations capable of synthesizing peptidoglycan, vancomycin caused a decrease in the incorporation of isotope from CDP-glycerol into polymer. Synthesis of the poly (glycerol phosphate) unit thus depended at an early stage on the concomitant synthesis of wall teichoic acid and later on the synthesis of peptidoglycan. It is concluded that CDP-glycerol is the biosynthetic precursor of the tri(glycerol phosphate) linkage unit between teichoic acid and peptidoglycan that has recently been characterized in S. aureus H.

Bacillus subtilis↗
PubMed1975

Specific recognition of choline residues in the cell wall teichoic acid by the N-acetylmuramyl-L-alanine amidase of Pneumococcus.

Pneumococci growing on choline-containing medium are known to incorporate this amino alcohol into the wall teichoic acid and produce autolysin-sensitive cell walls. In contrast, bacteria grown on the choline analogue, ethanolamine, incorporate ethanolamine into the teichoic acid and synthesize cell walls that are resistant to the homologous autolysin. In this communication, we report experiments aimed at understanding the biochemical mechanism of this phenomenon. Ethanolamine-containing (autolysin-resistant) cell walls were methylated in vitro with methyl iodide. Under appropriate conditions, virtually all of the ethanolamine residues could be converted to choline. After methylation, the formerly autolysin-resistant walls could be quantitatively hydrolyzed by the pneumococcal autolysin. Methylated walls also recovered another property typical of cell walls isolated from choline-grown bacteria: they could induce the in vitro "conversion" of an inactive form of autolysin to the catalytically active form (Tomasz, A., and Westphal, M. (1971) Proc. Natl. Acad. Sci. U.S.A. 68, 2627-2630). The results suggest that the autolysin-catalyzed hydrolysis of amide bonds in the peptidoglycan requires an additional interaction between the enzyme protein and choline residues in the teichoric acid portion of the cell wall.

Alanine↗
PubMed1971

Abnormal autolytic enzyme in a pneumococus with altered teichoic acid composition.

Pneumococci in which the choline component of the cell wall teichoic acid was replaced by ethanolamine contain an abnormal autolytic enzyme that has a low molecular weight and low activity in contrast to the enzyme typical of choline-containing bacteria that has a high molecular weight and high activity. The abnormal autolysin can be converted to the normal (cholinetype) enzyme by incubation in vitro with choline-containing cell walls.

Amino Alcohols↗
PubMed1984

Occurrence of phlyctenules after immunization with ribitol teichoic acid of Staphylococcus aureus.

We immunized rabbits to ribitol teichoic acid (RTA), a component of the cell wall of Staphylococcus aureus, by intravenous injections of RTA-sensitized sheep RBCs. Hemagglutination titers to RTA and corneal phlyctenules developed in these rabbits after topical challenge with viable S aureus, but did not develop in control rabbits immunized with unsensitized sheep RBCs. These results suggest that hypersensitivity to RTA, the major antigenic determinant of S aureus, plays a role in the development of corneal phlyctenules.

Animals↗
PubMed1974

Antigens of Streptococcus mutans. II. Characterization of an antigen resembling a glycerol teichoic acid in walls of strain BHT.

Cold 10% trichloroacetic acid was used to extract antigens from purified cell walls of Streptococcus mutans BHT. Column chromatography on Biogel P-100 resolved two serologically reactive fractions (B and C). These fractions were ascertained to be relatively pure by recycling on Biogel P-100, Ouchterlony double-diffusion analysis, and immunoelectrophoresis. Fractions B and C demonstrated bands of absolute homology by double-diffusion but different mobilities by immunoelectrophoresis. Chemical analysis indicated that fraction B is a polysaccharide composed principally of rhamnose and galactose, with smaller amounts of glucose and glucosamine. Small quantities of glycerol and phosphorus also were found. Fraction C was composed mainly of galactose, glycerol, and phosphorus. Alkaline hydrolysis of this fraction yielded products typically released by the degradation of a glycerol teichoic acid, such as glycerol monophosphate, glycerol diphosphate, inorganic phosphorus, and several glycosyl glycerol phosphates. Diglycerol triphosphate was not detected. Side-group analysis revealed that glycerol was substituted by mono- and trigalactosyl moieties. Fraction C was deduced to contain 25 glycerol phosphate units per polymer length. Hapten inhibition studies revealed a beta-galactoside as the probable hapten on this antigen. The BHT teichoic acid reacted strongly with FA-1 antiserum. It showed bands of homology with both BHT and FA-1 crude acid extracts upon double-diffusion, using antisera to either strain. The BHT teichoic acid also displayed immunoelectrophoretic behavior identical to one of the mobile FA-1 cell wall antigens, again using either serum to develop precipitin bands. It is concluded this antigen may possess a serotype-specific determinant for S. mutans serotype b.

Acrylamides↗
PubMed1999

Cell wall teichoic acids of Actinomadura viridis VKM Ac-1315T.

The cell walls of Actinomadura viridis contain poly(glycosylglycerol phosphate) chains of complex structure. On the basis of NMR spectroscopy of the polymer and glycosides thereof the following structural units were found: beta-D-Galp3Me-(1-->4)[beta-D-Glcp-(1-->6)]-beta-D-Galp-(1-->1)-++ +snGro (G1); beta-D-Galp-(1-->4)-beta-D-Galp-(1-->1)-snGro (G2); beta-D-Galp3Me-(1-->4)-beta-D-Galp-(1-->1)-snGro (G2a); beta-D-Galp-(1-->1)-snGro (G3); beta-D-Galp-(1-->1)[beta-D-Galp-(1-->2)]-snGro (G4); beta-D-Glcp-(1-->2)-snGro (G5). Glycosides G1, G2 and G3 were the predominant components of the teichoic acid: they formed the polymer chain via phosphodiester bonds involving C-3 of the glycerol residue and C-3 of the galactosyl residue which in turn glycosylates C-1 of the glycerol residue. Whether the different glycosides make up the one chain or whether there are several poly(glycosylglycerol phosphate) chains in the cell wall remains to be determined. It was suggested that the minor component G5 is located at the nonterminal end of the chains. Compound G4 which contains disubstituted glycerol residues (unusual for the teichoic acid) was also found as a minor component; this may be the glycoside of a new type of teichoic acid, or a glycoside on the terminal end of the above mentioned chains. In addition, small amounts of 1,3-poly(glycerol phosphate) chains were found in the cell wall.

Actinomycetales↗
PubMedDate not supplied

The role of antibodies against alpha-toxin and teichoic acid in the diagnosis of staphylococcal infections.

An enzyme-linked immunosorbent assay (ELISA) was used with purified alpha-toxin and teichoic acid preparations to measure the IgG and IgM response in Staphylococcus aureus infections. After determining antibodies in a normal population, cut-off levels were set for all age groups. ELISA with alpha-toxin was more sensitive than the antistaphylolysin neutralization test (ASTA). Determining IgM antibodies with the two antigens was found to be of limited diagnostic value. Positive IgG titers against alpha-toxin were found in 21 of 27 patients (78%) with endocarditis, 11 of 14 (79%) with complicated septicemia, eight of 20 (40%) with uncomplicated septicemia and in 12 of 22 (54%) with chronic osteomyelitis. The IgG responses to teichoic acid and alpha-toxin were somewhat different when measured by ELISA, and the parallel performance of the two assays resulted in improved serological diagnostics. The number of positive patients increased to 89%, 86%, 65% and 64%, respectively, in the four groups with a diagnostic specificity of 93%. In septicemic staphylococcal infections, the diagnosis could be established in all patients (28 of 28) with adequately spaced paired samples.

Adolescent↗
PubMed1972

Teichoic acid hydrolase activity in soil bacteria (Bacillus subtilis-sporulation-phosphodiesterase-polyamines-concanavalin A).

Bacterial phosphodiesterases have been found that are capable of cleaving the backbone of teichoic acid. Such enzymes have not been reported previously. An aerobic, gram-negative, rod-shaped bacterium producing this activity was detected and isolated by autoradiography of soil suspensions growing on minimal medium containing (32)P-labeled Bacillus subtilis ATCC 6051 cell walls as the sole phosphorus source. Broken-cell preparations are capable of depolymerizing teichoic acids in media of low ionic strength at near-neutral pH values. An active teichoicase is also present in B. subtilis, ATCC 6051 (the Marburg strain), especially in sporulating cultures.

Autoradiography↗
PubMed1998

Structure of teichoic acid of the cell wall of Streptomyces sparsogenes VKM Ac-1744T.

The cell wall of Streptomyces sparsogenes VKM Ac-1744T contains a teichoic acid of 1,3-poly(glycerol phosphate) type. The polymer is composed of about 11 repeating units of the following structure: The structure was not identified in gram-positive bacteria previously. The data are in agreement with DNA-relatedness between Streptomyces sparsogenes and Streptomyces hygroscopicus species and suggest the species-specificity of teichoic acid structure in the studied streptomycetes group.

Carbohydrate Sequence↗
PubMed1986

Structure and functions of linkage unit intermediates in the biosynthesis of ribitol teichoic acids in Staphylococcus aureus H and Bacillus subtilis W23.

The stepwise formation and characterization of linkage unit intermediates and their functions in ribitol teichoic acid biosynthesis were studied with membranes obtained from Staphylococcus aureus H and Bacillus subtilis W23. The formation of labeled polymer from CDP-[14C]ribitol and CDP-glycerol in each membrane system was markedly stimulated by the addition of N-acetylmannosaminyl(beta 1----4)N-acetylglucosamine (ManNAc-GlcNAc) linked to pyrophosphorylyisoprenol. Whereas incubation of S. aureus membranes with CDP-glycerol and ManNAc-[14C]GlcNAc-PP-prenol led to synthesis of (glycerol phosphate) 1-3-ManNAc-[14C]GlcNAc-PP-prenol, incubation of B. subtilis membranes with the same substrates yielded (glycerol phosphate)1-2-ManNAc-[14C]GlcNAc-PP-prenol. In S. aureus membranes, (glycerol phosphate)2-ManNAc-[14C]GlcNAc-PP-prenol as well as (glycerol phosphate)3-ManNAc-[14C]GlcNAc-PP-prenol served as an acceptor for ribitol phosphate units, but (glycerol phosphate)-ManNAc-[14C]GlcNAc-PP-prenol did not. In B. subtilis W23 membranes, (glycerol phosphate)-ManNAc-[14C]GlcNAc-PP-prenol served as a better acceptor for ribitol phosphate units than (glycerol phosphate)2-ManNAc-[14C]GlcNAc-PP-prenol. In this membrane system (ribitol phosphate)-(glycerol phosphate)-ManNAc-[14C]GlcNAc-PP-prenol was formed from ManNAc-[14C]GlcNAc-PP-prenol, CDP-glycerol and CDP-ribitol. The results indicate that (glycerol phosphate)1-3-ManNAc-GlcNAc-PP-prenol and (glycerol phosphate)1-2-ManNac-GlcNAc-PP-prenol are involved in the pathway for the synthesis of wall ribitol teichoic acids in S. aureus H and B. subtilis W23 respectively.

Bacillus subtilis↗
PubMed1980

Interaction of Streptococcus mutans glucosyltransferases with teichoic acids.

The Streptococcus mutans GS5 glucosyltransferase activities (both water-soluble and -insoluble glucan-synthesizing fractions) were inhibited by purified lipoteichoic acid. In vitro sucrose-dependent colonization of smooth surfaces by strain GS5 was also markedly reduced in the presence of the amphipathic molecules. The inhibition of soluble glucan synthesis by lipoteichoic acid appeared to be competitive with respect to both sucrose and primer dextran T10. These inhibitory effects were dependent on the presence of the fatty acid components of lipoteichoic acid since deacylated lipoteichoic acids did not inhibit glucosyltransferase activity. However, the deacylated molecules did interact with the enzymes since deacylated lipoteichoic acid partially protected the enzyme activity against heat inactivation and also induced the formation of high-molecular-weight enzyme complexes from the soluble glucan-synthesizing fraction. The presence of teichoic acid in high-molecular-weight aggregates of glucosyltransferase isolated from the culture fluids of strain GS5 was suggested by the detection of polyglycerophosphate in these fractions. In addition to strain GS5, two other organisms containing polyglycerophosphate teichoic acids, Lactobacillus casei and Lactobacillus fermentum, were demonstrated to bind glucosyltransferase activity. These results are discussed relative to the potential role of teichoic acid-glucosyltransferase interactions in enzyme binding to the cell surface of S. mutans and the formation of high-molecular-weight enzyme aggregates in the culture fluids of the organism.

Acylation↗
PubMed1976

Cell wall assembly in Bacillus subtilis: development of bacteriophage-binding properties as a result of the pulsed incorporation of teichoic acid.

Addition of a pulse of excess phosphate to a phosphate-limited culture of Bacillus subtilis W23 resulted in the synthesis and incorporation of wall material that contained teichoic acid. Consequently, the bacteria regained the ability to bind phage SP50 although maximum phage-binding properties did not develop until approximately half a generation time after incorporation of teichoic acid had ceased. The present findings strongly support our earlier suggestion that newly synthesized receptor material is incorporated at the inner surface of the wall and becomes exposed at the outer surface only during subsequent growth.

Adsorption↗
PubMed1986

Structural studies of a teichoic acid from Streptococcus agalactiae type III.

An unusual type of teichoic acid has been isolated from Streptococcus agalactiae type III. It has the same backbone as the lipoteichoic acid from Streptococcus faecalis, but is devoid of fatty acid residues, a phosphatidyl group, and substituents in the poly(glycerol phosphate) side-chain. The following structure, with n approximately 20, was determined mainly with the aid of n.m.r. spectroscopy. (Formula: see text)

Carbohydrate Conformation↗
PubMed2006

Cell wall teichoic acids of streptomycetes of the phenetic cluster 'Streptomyces fulvissimus'.

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 (alpha-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.

Carbohydrate Conformation↗
PubMed2006

Identification of an essential gene of Listeria monocytogenes involved in teichoic acid biogenesis.

Listeria monocytogenes is a facultative intracellular gram-positive bacterium responsible for severe opportunistic infections in humans and animals. We had previously identified a gene encoding a putative UDP-N-acetylglucosamine 2-epimerase, a precursor of the teichoic acid linkage unit, in the genome of L monocytogenes strain EGD-e. This gene, now designated lmo2537, encodes a protein that shares 62% identity with the cognate epimerase MnaA of Bacillus subtilis and 55% identity with Cap5P of Staphylococcus aureus. Here, we addressed the role of lmo2537 in L. monocytogenes pathogenesis by constructing a conditional knockout mutant. The data presented here demonstrate that lmo2537 is an essential gene of L. monocytogenes that is involved in teichoic acid biogenesis. In vivo, the conditional mutant is very rapidly eliminated from the target organs of infected mice and thus is totally avirulent.

Animals↗
PubMed1982

Assay of teichoic acid antibodies and antistaphylolysin in the diagnosis of Staphylococcal osteomyelitis.

Teichoic acid antibodies (TAA), measured by gel diffusion, and antistaphylolysin (ASa) values were determined in 46 osteomyelitis patients and 200 healthy controls. A positive TAA titer (greater than or equal to 4) was seen in 4/16 patients with acute hematogenous osteomyelitis caused by Staphylococcus aureus and in 7/22 patients with chronic staphylococcal osteomyelitis, while ASta was positive (greater than or equal to 2.0 IU/ml) in 9 patients in both groups all except 2 exceeding 4.0 IU/ml. No positive TAA titres or ASta values were seen in 8 patients with chronic nonstaphylococcal osteomyelitis. The rate of positive test results in 200 controls was 7% for TAA and 4% for ASta. Basing diagnosis on a positive value in either of the tests gave 21 positive results in 38 patients with staphylococcal osteomyelitis; 18 by ASta alone and 11 by TAA alone. Both tests were positive at the same time in 3 patients with acute and in 5 patients with chronic staphylococcal osteomyelitis but never in controls.

Adolescent↗
PubMed1983

Detection of anti-teichoic acid immunoglobulin G antibodies in experimental Staphylococcus epidermidis endocarditis.

An enzyme-linked immunosorbent assay (ELISA) was developed for the detection of rabbit immunoglobulin G (IgG) antibodies to purified cell wall teichoic acids from the Staphylococcus aureus Lafferty strain and three strains of coagulase-negative staphylococci. Significant immunological cross-reactivity occurred only between the teichoic acid of S. aureus and one coagulase-negative preparation. The ELISA was used to determine the serum IgG response to Staphylococcus epidermidis in a rabbit model of aortic valve endocarditis. Blood samples were drawn before inoculation and then every 5 days until death or sacrifice at 32 to 35 days postinoculation. Valve vegetations were culture positive at autopsy in 16 (59%) of the 27 catheterized rabbits. Antibody titers in this culture-positive group and the culture-negative group began to rise as early as day 6. Although both groups demonstrated an antibody response, the culture-positive group attained a significantly higher titer on days 26 and 31. Antibodies also rose in a control group of rabbits without a heart catheter but which were inoculated with bacteria. Again, the antibody titer was significantly less than that for the culture-positive group. This ELISA may be useful for the diagnosis of coagulase-negative staphylococcal infections in humans.

Animals↗