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The glycerol teichoic acid of walls of Staphylococcus lactis I3.

ABSTRACT: 1. The teichoic acid from walls of Staphylococcus lactis I3 was isolated by extraction with trichloroacetic acid and shown to contain glycerol, N-acetylglucosamine, phosphate and d-alanine in the molecular proportions 1:1:2:1. The alanine is attached to the polymer through ester linkages. 2. Hydrolysis with acid gave alanine, glucosamine and glycerol diphosphates. Under mild acid conditions a repeating unit was produced; this consists of glycerol diphosphate joined through a phosphodiester group to N-acetylglucosamine. 3. Hydrolysis with alkali gave glycerol diphosphates, saccharinic acid and two phosphodiesters containing glucosamine whose structures were elucidated; these both contain glucosamine 1-phosphate, and N-acetylglucosamine 1-phosphate was isolated by a degradative procedure. 4. The unusual properties of the teichoic acid are explained by a polymeric structure in which N-acetylglucosamine 1-phosphate is attached through its phosphate to glycerol phosphate. 5. The biosynthetic implications of this structure are discussed.

SUBMITTER: Archibald AR

PROVIDER: S-EPMC1187384 | biostudies-other | 1968 Dec

REPOSITORIES: biostudies-other

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The membrane teichoic acid of Staphylococcus lactis I3.

Project description:1. Teichoic acid was isolated by extraction with trichloroacetic acid of the membrane fraction of disrupted cells of Staphylococcus lactis I3. 2. The purified material contains glycerol, phosphate and alanine, but little or no sugar or amino sugar. 3. A study of the products of hydrolysis with acid and alkali established that the membrane teichoic acid is a (1-->3)-linked poly(glycerol phosphate) that differs in structure from the glycerol teichoic acid in the wall of this organism. 4. The alanine ester residues show the characteristic high lability to alkali and are thus distinguishable from the more stable alanine ester residues of the wall teichoic acid. 5. The significance of these structural features and the possible function of teichoic acids are discussed.

| S-EPMC1187386 | biostudies-other

The biosynthesis of the wall teichoic acid in Staphylococcus lactis I3.

Project description:1. The biosynthesis of the wall teichoic acid in Staphylococcus lactis I3 was studied. Cell-free particulate enzyme preparations, probably representing fragmented membrane, were isolated and used for the synthesis of polymer. 2. By using appropriately labelled CDP-glycerol and UDP-N-acetylglucosamine it was shown that the former contributes a glycerol phosphate residue and the latter contributes an N-acetylglucosamine 1-phosphate residue to the repeating unit. 3. No polymer was synthesized unless both nucleotides were present, and no other substrates were required. 4. The properties of the enzyme system were studied. 5. Although attempts to fractionate the system failed, the biosynthesis is believed to be complex and its mechanism is considered.

| S-EPMC1187387 | biostudies-other

Further studies on the glycerol teichoic acid of walls of Staphylococcus lactis I3. Location of the phosphodiester groups and their susceptibility to hydrolysis with alkali.

Project description:1. The teichoic acid from walls of Staphylococcus lactis I3 is readily degraded in dilute alkali. 2. Degradation proceeds by selective hydrolysis of that phosphodiester group attached to an alcoholic hydroxyl group of the N-acetylglucosamine and gives a repeating unit in high yield. 3. Further studies on a different repeating unit isolated by partial acid hydrolysis have shown that the glycerol diphosphate is attached to the 4-hydroxyl group of the N-acetylglucosamine and not to the 3-hydroxyl group as was proposed earlier. 4. The susceptibility towards hydrolysis by alkali of other structural types of teichoic acid has been examined and found to vary markedly according to their structure.

| S-EPMC1178059 | biostudies-other

The glycerol teichoic acid from walls of Staphylococcus epidermidis I2.

Project description:1. Walls of Staphylococcus epidermidis I2 contain 30% (w/w) of a glycerol teichoic acid containing phosphate, d-alanine and d-glucose in the molecular proportions 1:0.25:0.50. 2. The teichoic acid was isolated by extraction with trichloroacetic acid and with dilute aqueous NN-dimethylhydrazine at pH7, and was shown to be a (1-->3)-linked poly(glycerol phosphate) containing beta-d-glucopyranosyl and d-alanyl ester substituents. 3. 2-O-beta-d-Glucopyranosylglycerol was isolated and characterized as its crystalline hexa-O-acetate. 4. Unlike that of certain other bacteria, the peptidoglycan component of the wall is not solubilized by NN-dimethylhydrazine. 5. The membrane teichoic acid is also a (1-->3)-linked poly(glycerol phosphate) but contains a smaller proportion of glucosyl substituents.

| S-EPMC1187389 | biostudies-other

Lipid intermediates in the biosynthesis of the wall teichoic acid in Staphylococcus lactis 13.

Project description:1. Particulate enzyme systems have been prepared from Staphylococcus lactis I3 which effect the synthesis of wall teichoic acid (a polymer containing a repeating unit in which d-glycerol 1-phosphate is attached to the 4-position on N-acetylglucosamine 1-phosphate) from the nucleotide precursors CDP-glycerol and UDP-N-acetylglucosamine. By using nucleotides labelled with (32)P and (14)C it has been shown that the synthesis proceeds via lipid intermediates. 2. Two intermediates have been found. In one of these N-acetylglucosamine 1-phosphate is present, whereas in the other the repeating unit of the teichoic acid occurs. 3. The simultaneous formation of the teichoic acid, a poly-(N-acetylglucosamine 1-phosphate) and an unidentified lipid, together with the poor ability of most particulate systems to synthesize polymer and the instability of the lipid intermediates themselves, have interfered with pulse-labelling experiments. Nevertheless, the biosynthetic sequence has been elucidated. It is concluded that the intermediates are derivatives of undecaprenol phosphate.

| S-EPMC1178557 | biostudies-other

The structure and possible function of the glycolipid from Staphylococcus lactis I3.

Project description:1. The total lipid was extracted from Staphylococcus lactis I3 with chloroform-methanol mixtures and the glycolipid component was isolated by chromatography on silicic acid. 2. Saponification yielded a non-crystalline glycoside for which the structure O-beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranosyl-(1-->1)-d-glycerol has been established by chemical degradations and by comparison with synthetic material. 3. The role of the glycosyl diglycerides in bacterial membranes is discussed.

| S-EPMC1198390 | biostudies-other

Evaluation of polysaccharide intercellular adhesion (PIA) and glycerol teichoic acid (Gly-TA) arisen antibodies to prevention of biofilm formation in Staphylococcus aureus and Staphylococcus epidermidis strains.

Project description:OBJECTIVE:Staphylococcus aureus and S. epidermidis as opportunistic pathogens, notable for their frequency and severity of infections are recognized as the most usual reasons for medical device-associated infections that strike hospitalized patients and also immunocompromised individuals. In this study, the polysaccharide intercellular adhesion (PIA) and Glycerol teichoic acid) Gly-TA) as two major macromolecules in the biofilm formation process were purified under the native condition and their structure was analyzed by using colorimetric assays and Fourier Transform Infrared spectroscopy (FTIR). Afterward, the immune response of macromolecules and the mixture of them were assessed by measuring total IgG titers. Subsequently, biofilm inhibitory effects of raising antibodies to biofilm former S. aureus and S. epidermidis were evaluated. RESULTS:Obtained data were shown a significant rise in levels of antibodies in immunized mice with mentioned antibodies in comparison with the control group. According to the obtained findings, mentioned antibodies could eliminate S. aureus and S. epidermidis biofilm formation in vitro assays. This survey confirms the proposal that immunization of mice with a mixture of Gly-TA and PIA vaccine could be secure and protected against S. epidermidis and S. aureus infection.

| S-EPMC6815028 | biostudies-literature

Wall Teichoic Acid Glycosylation Governs Staphylococcus aureus Nasal Colonization.

Project description:UnlabelledNasal colonization by the human pathogen Staphylococcus aureus is a major risk factor for hospital- and community-acquired infections. A key factor required for nasal colonization is a cell surface-exposed zwitterionic glycopolymer, termed wall teichoic acid (WTA). However, the precise mechanisms that govern WTA-mediated nasal colonization have remained elusive. Here, we report that WTA GlcNAcylation is a pivotal requirement for WTA-dependent attachment of community-acquired methicillin-resistant S. aureus (MRSA) and emerging livestock-associated MRSA to human nasal epithelial cells, even under conditions simulating the nutrient composition and dynamic flow of nasal secretions. Depending on the S. aureus strain, WTA O-GlcNAcylation occurs in either α or β configuration, which have similar capacities to mediate attachment to human nasal epithelial cells, suggesting that many S. aureus strains maintain redundant pathways to ensure appropriate WTA glycosylation. Strikingly, a lack of WTA glycosylation significantly abrogated the ability of MRSA to colonize cotton rat nares in vivo. These results indicate that WTA glycosylation modulates S. aureus nasal colonization and may help to develop new strategies for eradicating S. aureus nasal colonization in the future.ImportanceNasal colonization by the major human pathogen Staphylococcus aureus is a risk factor for severe endogenous infections and contributes to the spread of this microbe in hospitals and the community. Here, we show that wall teichoic acid (WTA) O-GlcNAcylation is a key factor required for S. aureus nasal colonization. These data provide a mechanistic explanation for the capacity of WTA to modulate S. aureus nasal colonization and may stimulate research activities to establish valuable strategies to eradicate S. aureus nasal colonization in high-risk hospitalized patients and in the general community.

| S-EPMC4488942 | biostudies-literature

Glycosylation of wall teichoic acid in Staphylococcus aureus by TarM.

Project description:Wall teichoic acid (WTA) glycopolymers are major constituents of cell envelopes in Staphylococcus aureus and related gram-positive bacteria with important roles in cell wall maintenance, susceptibility to antimicrobial molecules, biofilm formation, and host interaction. Most S. aureus strains express polyribitol phosphate WTA substituted with D-alanine and N-acetylglucosamine (GlcNAc). WTA sugar modifications are highly variable and have been implicated in bacteriophage susceptibility and immunogenicity, but the pathway and enzymes of staphylococcal WTA glycosylation have remained unknown. Revisiting the structure of S. aureus RN4220 WTA by NMR analysis revealed the presence of canonical polyribitol phosphate WTA bearing only alpha-linked GlcNAc substituents. A RN4220 transposon mutant resistant to WTA-dependent phages was identified and shown to produce altered WTA, which exhibited faster electrophoretic migration and lacked completely the WTA alpha-GlcNAc residues. Disruption of a gene of unknown function, renamed tarM, was responsible for this phenotype. Recombinant TarM was capable of glycosylating WTA in vitro in a UDP-GlcNAc-dependent manner, thereby confirming its WTA GlcNAc-transferase activity. Deletion of the last seven amino acids from the C terminus abolished the activity of TarM. tarM-related genes were found in the genomes of several WTA-producing bacteria, suggesting that TarM-mediated WTA glycosylation is a general pathway in gram-positive bacteria. Our study represents a basis for dissecting the biosynthesis and function of glycosylated WTA in S. aureus and other bacteria.

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(Automated) Synthesis of Well-defined Staphylococcus Aureus Wall Teichoic Acid Fragments.

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| S-EPMC8361686 | biostudies-literature

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