Structure of the intracellular glycerol teichoic acid from Lactobacillus casei A.T.C.C. 7469

Abstract

Although the walls of Lactobacillus casei A. T. C. C. 7469 contain no detectable amounts of teichoic acid, a glycerol teichoic acid was detected within the cells. This compound has been isolated and partially purified by extraction of cells or cell contents with trichloroacetic acid and reprecipitation several times with ethanol. On acid hydrolysis it gives glycerol, its mono- and di-phosphate and alanine. With hot alkali the products include the alkali-stable diglycerol tri-phosphate. The structure of this triphosphate was established by hydrolysis to the diglycerol phosphate with prostatic phosphomonoesterase. The phosphodiester was hydrolyzed with alkali to glycerol and its mono-phosphates. It follows that the teichoic acid is a polymer in which glycerol residues are joined through phosphodiester linkages at positions 1 and 3 in the glycerol units. The alanine from the polymer is readily oxidized with a D-amino acid oxidase, and thus has the D-configuratioa Alanine is joined to the polymer through ester linkages at the 2-position of each glycerol residue. The structure is assigned to this intracellular teichoic acid. The alanine ester groups are highly reactive towards alkali and amines. They react with hydroxylamine at about the same rate as do amino acids in combination with ribonucleic acid.