Teichoic acid

Teichoic Acids.—Recent reviews have referred to the occurrence and functions of membrane teichoic acids, the biosynthesis of bacterial cell walls and of teichoic acids in bacterial cell walls and membranes, and the surface carbohydrates of prokaryotic cells.  

The ribitol teichoic acids in whole cells and isolated cell walls of Bacillus suhtilis W23 have been determined by g.l.c., which was used to measure ribitol and 2-0-P-D-glucopyranosyl-L-ribitol (as the TMS derivatives) following degradation of the teichoic acids with 60% hydrogen fluoride.  

Studies of the effects of thermal stress on three strains of Staphylococcus aureus have indicated that the teichoic acid in the cell walls aids the survival of the cells by maintaining the accessible pool of Mg ions on the cell surface. A spore-forming Gram-negative bacterium with properties closely similar to those of Bacillus circulans, and which hydrolyses the 2-acetamido-2-deoxy-D-glucosylribitol teichoic acid from Staph, aureus, has been isolated from soil. The immunogenicities of teichoic and lipoteichoic acids from the cell walls and plasma membranes of several oral bacteria that produce lactic acid have been reported. 

Duckworth, in Surface Carbohydrates of the Prokaryotic Cell , ed. I. W. Sutherland, Academic Press, New York and London, 1977, p. 177. 

Tochikubo, K. Kato, T. Hirata, S. Kotani, and K. Yagi, Japan J. Microbiol., 1976, 20, 123. 

More complex teichoic acids occur that have an alternating structure of glycerol joined to the C-4-OH of N-acetyl-2-amino-2-deoxy-a-D-glucopyranosyl-l-phosphate by a phosphodiester linkage, with the a-1-phosphate joined to C-1-OH of the next glycerol unit [200] (see Fig. 6.21C). 

A polysaccharide that is very closely related in structure to the teichoic acids is an O-phospho-D-mannan, elaborated by yeasts of the Hansenula genus. The polysaccharide differs from the usual teichoic acids in that the carbohydrate unit is an 

The teichoic acids are water soluble and obtained from the cell walls of grampositive bacteria by hydrolysis of the acid-labile glucosaminyl-1-phosphate linkage. The bacterial cells are washed with saline and then treated with cold (4°C) 10% trichloroacetic acid in a blender for 1 min. The hydrolysis is then allowed to proceed for 15 hr at 0°C. The solution of solubilized teichoic acid solution is neutralized, and the teichoic acids are precipitated by the addition of one or two volumes of ethanol. The ethanol solution is allowed to stand 12 hr at 0°C, and the precipitated teichoic acid is removed by centrifugation [197]. 

The function of the teichoic acids in the bacterial cell wall has not been definitely determined. Shortly after their discovery in the late 1950s, it was suggested that they function in the control of the concentration of cations in the cell wall. There was some evidence that they played a role in the balance of divalent cations in membranes and thereby provided membrane integrity and stability to the enzymes in the membrane and cell wall [203]. 

Teichoic acids have also been implicated in the extracellular secretion of enzymes by bacteria. Treatment of Bacillus amyloliquefaciens with tunicamycin, an antibiotic known to inhibit cell wall synthesis, produced cells that were deficient in teichoic acid and did not secrete a-amylase. The a-amylase was found to be cell bound. The accumulation of a-amylase in the cell was also observed when teichoic acid synthesis was inhibited by culturing the organism in a medium that was limited in phosphate. Further evidence of the involvement of teichoic acids in protein secretion was obtained by using mutants that did not synthesize teichoic acids. These mutants also had a marked decrease in the amount of a-amylase that was secreted [204]. 

Teiehoic Acids.—The C n.m.r. spectra of a number of ribitol teichoic acids substituted with glycosyl residues, and of their dephosphorylated repeating units, have been recorded. Identical spectra are obtained for teichoic acids substituted with 2-0- and 4-0-glycosyl residues, so it is not possible to differentiate between these positional isomers by this technique. 

The complete structural analysis of the complex polysaccharide C-substance from Streptococcus pneumoniae type 1 includes the identification of a d-glucopyranosyl residue and a 2-acetamido-2-deoxy-D-galactosyl residue in its repeating unit. By application of methylation analysis and H and C n.m.r. 

spectra of a number of ribitol teichoic acids substituted with 

Investigation of the cell-wall composition and associated properties of strains of Staphylococcus aureus, which are resistant to methicillin, has not revealed evidence for any unusual wall polymers/ The ribitol teichoic acid isolated from Staphylococcus hyicus contains 2-acetamido-2-deoxy-D-glucosyl residues. Interaction of the teichoic acid with concanavalin A, and its susceptibility to 0C-, but not to 3-D-2-acetamido-2-deoxyglucosidase, showed that the amino-sugar is in the a-configuration. 

The cell walls of Streptococcus pneumoniae contain a teichoic acid (C polysaccharide) composed of 2-acetamido-2-deoxy-D-galactose, 2-acetamido-4-amino-2,4,6-trideoxy-D-hexose, ribitol phosphate, choline phosphate, and D-glucose. From the results of periodate oxidation and methylation analysis, together with an examination of the n.m.r. spectra, the structure (1) has been proposed. It is speculated that the C-3 hydroxy-group of the chain terminal diaminotrideoxy-D-hexose unit is glycosylated with isomaltose. 

Pneumococcal cell-wall teichoic acid, rather than peptidoglycan, is considered to be responsible for the activation of the alternative complement pathway. This contrasts with group A streptococci in which the greatest activity was found associated with a heat labile protein of the cell membrane. 

Phosphate-repressible phosphodiesterases, isolated from Bacillus subtilis, have been reported to be responsible for the depolymerization of teichoic acids.  

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Teichoic acids (16) are bacterial polymers in which alditols, glycerol, or ribitol are joined through the primary hydroxyl groups via phosphate diester linkages. 

Lipoteichoic acids (from gram-positive bacteria) [56411-57-5J. Extracted by hot phenol/water from disrupted cells. Nucleic acids that were also extracted were removed by treatment with nucleases. Nucleic resistant acids, proteins, polysaccharides and teichoic acids were separated from lipoteichoic acids by anion-exchange chromatography on DEAE-Sephacel or by hydrophobic interaction on octyl-Sepharose [Fischer et al. Ear J Biochem 133 523 1983]. 

FIGURE 9.25 Teichoic acids are covalently linked to the peptidoglycan of Grampositive bacteria. These polymers of (a, b) glycerol phosphate or (c) ribitol phosphate are linked by phosphodiester bonds. 

Ribitol teichoic acid from Bacillus subHUs... 

Klosinski, P., Penczek, S. Teichoic Acids and Their Models Membrane Biopolymers withPolphosphate Backbones. Synthesis, Structure and Properties. Vol. 79, pp. 139—157. 

Five pentoses, namely, D-ribose, d- and L-arabinose, and D- and L-xylose, have been found in hydrolyzates of bacterial polysaccharides. D-Riboseisthe most common of these, and is a component of different LPS, capsular polysaccharides, and teichoic acid type of polymers. In all these polymers, it occurs as the /I-furanosyl group or residue. 

Cyclic acetals of pyruvic acid are common in extracellular polysaccharides (compare, for example, Ref. 6). They have also been found in some LPS, namely, those from Shigella dysenteriae type 6 and E. coli 0-149 (Ref. 139), and in the teichoic acid from Brevibacterium iodinum. The biosynthesis of these acetals has already been discussed. 

Klebsiella K12, pyruvic acid is acetalically linked to 0-5 and 0-6 of a y -D-galactofuranosyl residue. Pyruvic acid is further acetalically linked to 0-4 and 0-5 of a D-mannitol residue in an unusual type of teichoic acid from Brevibacterium iodinum The absolute configuration at the acetalic carbon atom is (S) in the 5. pneumoniae type 4 polysaccharide, but it has not yet been determined for the other polymers. 

Many bacterial polysaccharides contain phosphoric ester groups. There is a limited number of examples of monoesters. More common are phosphoric diesters, connecting an amino alcohol or an alditol to the polysaccharide chain. Another possibility is that oligosaccharide or oligosaccharide-alditol repeating units are connected to a polymer by phosphoric diester linkages. In addition to the intracellular teichoic acids, several bacteria, for example, different types of Streptococcus pneumoniae, elaborate extracellular polymers of this type. These polymers are generally discussed in connection with the bacterial polysaccharides. 

Several of the intracellular teichoic acids are polymers of glycerol phosphate or ribitol phosphate. An unusual teichoic acid, composed of d-mannitol phosphate, and with pyruvic acid linked as an acetal to 0-4 and 0-5, has been isolated from Brevibacterium iodinum. ... 

In different polysaccharides of the teichoic acid type, monosaccharides or oligosaccharides are connected by phosphoric diester linkages. Two examples are the capsular antigens from Neisseria meningitides type A (56) and Haemophilus influenzae type c (57), respectively. Glycerol phosphate... 

Fig. 1.3 A, glycerol teichoic acid B, ribitol teichoic acid G, 3-10 glycosyl Ala, D-alanyl.

The major type-specific antigens of Gram-positive bacteria are the teichoic acid moieties associated with the cell wall (see Chapter 1). 

TRIGGERING MOLECULES (endotoxins, exotoxins, teichoic acid, etc.)... 

Brundish, D.E. and Baddiley, J. (1968) Pneumococcal C-substance, a ribitol teichoic acid containing choline phosphate. BiochemicalJournal 110, 573-582. 

Neuhaus FC, Baddiley J (2003) A continuum of anionic charge structures and functions of D-alanyl-teichoic acids in Gram-positive bacteria. Microbiol Mol Biol R 67 686-723... 

Kennedy LD (1974) Teichoic-acid synthesis in Bacillus-stearothermophilus. Biochem J... 

Baddiley, J. (1989). Bacterial cell walls and membranes. Discovery of the teichoic acids, Bioessays, 10, 207-210. 

Carbon-13 Chemical-Shifts of the Glycerol Residue of a Teichoic Acid and Its Components... 

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