Structural studies on the minor teichoic acid of Bacillus coagulans AHU 1631.
The minor teichoic acid linked to glycopeptide was isolated from lysozyme digests of Bacillus coagulans AHU 1631 cell walls, and the structure of the teichoic acid moiety and its junction with the peptidoglycan were studied. Hydrolysis of the teichoic-acid--glycopeptide complex with hydrogen fluoride gave a nonreducing oligosaccharide composed of glucose, galactose and glycerol in a molar ratio of 3:1:1 which was presumed to be dephosphorylated repeating units of the polymer chain. From the results of structural analysis involving NaIO4 oxidation, methylation and acetolysis, the above fragment was characterized as glucosyl(beta 1----3)glucosyl(beta 1----6)galactosyl(beta 1----6)glucosyl(alpha 1----1/3)glycerol. In addition, the Smith degradation of the complex yielded a phosphorus-containing fragment identified as glycerol-P-6-glucosyl(beta 1----1/3)glycerol. These results led to the most likely structure for the repeating units of the teichoic acid, -6[glucosyl(beta 1----3)]glucosyl(beta 1----6)galactosyl(beta 1----6)glucosyl(alpha 1----1/3)glycerol-P-. The minor teichoic acid, just like the major teichoic acid bound to the linkage unit, was released by heating the cell walls at pH 2.5. The mild alkaline hydrolysis of the minor teichoic acid after reduction with NaB3H4 gave labeled saccharides characterized as glucosyl(beta 1----6)galactitol and glucosyl(beta 1----3)glucosyl(beta 1----6)galactitol, together with a large amount of the unlabeled repeating units of the teichoic acid chain. Thus, the minor teichoic acid chain is believed to be directly linked to peptidoglycan at the galactose residue of the terminal repeating unit without a special linkage sugar unit.
D000096:Acetone; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D001407:Bacillus / Q000032:analysis*; D002241:Carbohydrates / Q000302:isolation & purification; D002473:Cell Wall / Q000032:analysis; D055598:Chemical Phenomena; D002621:Chemistry; D006020:Glycopeptides / Q000302:isolation & purification; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D013682:Teichoic Acids / Q000096:biosynthesis / Q000302:isolation & purification*; D014415:Tunicamycin / Q000031:analogs & derivatives
D000900:Anti-Bacterial Agents; D002241:Carbohydrates; D006020:Glycopeptides; D013682:Teichoic Acids; D014415:Tunicamycin; C017012:antibiotic 24010; D000096:Acetone