Teichoic acids synthesis

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

Figure 3.3 Teichoic Acid Synthesis. The undecaprenol cycle for sequences of the form (-A-P-B-P-),...

Chain Initiation and Termination in Teichoic Acid Synthesis... 

CDP-ethanolamine -4- a,/S-diglyceride — CMP phosphatidylethanolamine CDP-choline - - a,0-diglyceride CMP + lecithin CDP-choline - - iV-acylsphingosine — sphingomyelin CMP CDP-a,0-diglyceride -1- serine — phosphatidylserine - - CMP Teichoic Acid Synthesis... 

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]. 

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

Synthetic ribitol phosphate polymer, unlike teichoic acid in a wall, is readily extracted from the particulate enzyme or membrane preparation by treatment with phenol.18 Similarly, teichoic acid synthesized by intact cells in the presence of penicillin is only loosely attached to the wall,111 and it may be significant that, in each case, synthesis of teichoic acid has occurred without the simultaneous synthesis of glycosaminopeptide. It is now known that, in the normal wall, teichoic acid and glycosaminopeptide are attached to each other, and it has been suggested that the low activity of cell-free synthetase is due to the absence of suitable acceptor molecules of glycosaminopeptide. This possibility could account for the ease of removal of teichoic acid formed when simultaneous synthesis of glycosaminopeptide was not possible. 

Recently, the synthesis of l-deoxy-3-O-phosphono-D-glycerol-l-yl-P-D-gluco-pyranoside disodium salt 27 and its L-glycerol-l-yl isomer 31 was described 45). Compound 27 is a repeating unit of TA chains from Bacillus subtilis var. niger WM (formula 3). Both 27 and 31 were obtained mainly to record their l3C-NMR spectra to be further compared with the spectrum of the naturally occurring teichoic acid. Thus, 27 was prepared in a few-step synthesis as shown below ... 

Park and Strominger noticed the accumulation of a C3didine derivative in cultures of Staphylococcus aureus which had been inhibited by chloramphenicol, penicillin, or Crystal Violet. This cytidine derivative has been identified by Baddiley s group as cytidine ribitol pyrophosphate. Since these inhibitors affect the cell-wall synthesis, the data lend support to the belief that the cytidine compound is involved in the biosynthesis of a cell-wall constituent, and a likely candidate would be ribitol teichoic acid. 

As there is competition for isoprenoid lipid between lipo- and exopolysaccharide, peptidoglycan, and teichoic acids, the availability of isoprenoid lipid phosphate is one of the most critical factors affecting the synthesis of exopolysaccharide 236... 

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