Teichoic

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. 

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