Structural studies were carried out on the teichoic acids in cell walls of Listeria monocytogenes serotypes 3a, 4b, 4f, 6, and 7. The structure of the dephosphorylated repeating units, obtained by treatment with 46% hydrogen fluoride or alkaline hydrolysis, was examined by methylation analysis, acetolysis, and 1H-NMR spectroscopy. The results of Smith degradation of the teichoic acids and 13C-NMR spectroscopy led to the following most likely structures of the repeating units of the teichoic acids:----1-[N-acetylglucosaminyl(alpha 1----4)]ribitol-5-phosphate----for serotype 3a,----4-[galactosyl(alpha 1----6)][glucosyl(beta 1----3)]N -acetylglucosaminyl(beta 1----2)ribitol-5-phosphate----for serotype 4b,----4-[galactosyl(alpha 1----6)][N -acetylglucosaminyl(alpha 1----3)]N-acetylglucosaminyl(beta 1----2)ribitol -5-phosphate----for serotype 4f,----4-N-acetylglucosaminyl(beta 1----4)ribitol -5-phosphate----for serotype 6, and----1-ribitol-5-phosphate----for serotype 7. About 40% of the repeating units of the teichoic acid from serotype 4f were not substituted at C-3 of beta-N-acetylglucosaminyl residues.
The chemical compositions of the cell walls obtained from 10 strains (serotypes 1a, 3a, 4a, 4b, 4c, 4d, 4e, 4e, 4f, 6, and 7) of Listeria monocytogenes were analyzed. These cell walls were shown to be mainly composed of peptidoglycan and ribitol teichoic acids. Considerable variations in the composition of neutral sugars were observed among these cell walls. Chemical and NMR analyses indicated that the teichoic acids from L. monocytogenes serotypes 4a and 4d are composed of the following repeating units: Formula: See Text.
The lipoteichoic acids were isolated from phenol extracts of four Listeria strains representing serotypes 4a, 4b, 6a, and 6 to compare the differences in structure of amphiphilic polysaccharides from various serotypes of Listeria spp. The lipoteichoic acids from the four strains examined had the same structure in both hydrophilic chains and lipid portions. On the basis of the results of nuclear magnetic resonance spectroscopy and Smith degradation, the hydrophilic chains were shown to be 1,3-linked poly(glycerol phosphate) in which some of the glycerol residues had a-galactosyl substituents. The lipid portions were released by treatment with 46% hydrogen fluoride or 98% acetic acid. They were determined to be 3(1)-(2'-O-a-D-galactopyranosyl-a-Dglucopyranosyl)-1(3),2-diacylglycerol and 3(1)-[6'-phosphatidyl-2' -O-(a-D-galactopyranosyl)-a-Dglucopyranosyl]-1(3),2-diacylglycerol. The degrees of glycosyl substitution and proportions of the two lipids varied to some extent among these four strains.The antigenic scheme of Listeria spp., based on the somatic (0) and flagellar (H) antigens, includes 17 recognized serotypes, which can be divided into 13 groups by the differences in their somatic antigens (31). Ullmann and Cameron (35) reported the immunochemical properties of the cell wall carbohydrates of several serotypes of Listeria monocytogenes and described the monosaccharide constituents which should serve as the major antigenic determinant. Fiedler et al. (7) reported the composition of the cell walls from various serotypes of Listeria spp. and suggested that the glycosidic substituents of the cell wall teichoic acids determine the 0 antigenic specificities. Recently, the structures of cell wall teichoic acid from eight serotypes of Listeria spp. were reported (12,18,34), and some immunological properties of these teichoic acids were examined (18, 19) in our laboratory. In these studies, it seemed that the 0 serofactors of Listeria spp. cannot be entirely accounted for by cell wall teichoic acids; for instance, the structures of the cell wall teichoic acids from strain 5214 (serotype 4a) and strain 1383 (serotype 6) are identical (12,34). Therefore, other cell surface substances such as lipoteichoic acids also have to be taken into consideration in listerial 0 antigenicity.Lipoteichoic acids are membrane-associated amphiphilic molecules found in many gram-positive bacteria. They can act as surface antigens and often function as basis for serological classification of bacteria (20,39,40). Extracts obtained from L. monocytogenes contain apparent amphiphilic polysaccharides. The monocytosis-producing agent from serotype 1 cells is present in a high-molecularweight fraction containing phosphorus, lipids, and sugars (13). A phenol-water extract from serotype 1 cells contained a complex of peptide, polysaccharide, and lipid which had the biological activity of lipopolysaccharide (16,23 amphiphilic polysaccharide which was strikingly similar to gram-negative bacterial lipopolysaccharides in both chemical composition an...
The structure of polysaccharide prepared by lysozyme digestion from the cell wall of Propionibacterium acnes strain C7 was examined. The polysaccharide fraction was composed of glucose, galactose, mannose, galactosamine, and diaminomannuronic acid in a molar ratio of 1:1:0.3:1:2. By Smith degradation of the polysaccharide, diaminouronic acid-containing fractions were obtained, and the configuration of diaminouronic acid was identified as 2,3-diacetamido-2,3-dideoxymannuronic acid [Man(NAc)2A] by means of 1H-NMR and 13C-NMR spectroscopic analyses. The results of analyses involving methylation and partial acid hydrolysis led to the conclusion that the polysaccharide has the repeating unit----6)Gal(alpha 1----4)Man(NAc)2A(beta 1----6)Glc(alpha 1----4)Man(NAc)2A (beta 1----3)GalNAc(beta 1--. In addition, a portion of the galactose residues were substituted at C-4 by alpha 1----2 linked mannotriose.
Teichoic acid-glycopeptide complexes were isolated from lysozyme digests of the cell walls of Bacillus coagulans AHU 1631, AHU 1634, and AHU 1638, and the structure of the teichoic acid moieties and their linkage regions was studied. On treatment with hydrogen fluoride, each of the complexes gave a hexosamine-containing disaccharide, which was identified to be glucosyl(beta 1----4)N-acetylglucosamine, in addition to dephosphorylated repeating units of the teichoic acids, namely, galactosyl(alpha 1----2)glycerol and either galactosyl(alpha 1----2)[glucosyl(alpha 1----1/3)]glycerol (AHU 1638) or galactosyl(alpha 1----2)[glucosyl(beta 1----1/3)]glycerol (AHU 1631 and AHU 1634). From the results of Smith degradation, methylation analysis, and partial acid hydrolysis, the teichoic acids from these strains seem to have the same backbone chains composed of galactosyl(alpha 1----2)glycerol phosphate units joined by phosphodiester bonds at C-6 of the galactose residues. The presence of the disaccharide, glucosyl(beta 1----4)N-acetylglucosamine, in the linkage regions between teichoic acids and peptidoglycan was confirmed by the isolation of a disaccharide-linked glycopeptide fragment from each complex after treatment with mild alkali and of a teichoic acid-linked saccharide from each cell wall preparation after treatment with mild acid. Thus, it is concluded that despite structural differences in the glycosidic branches, the teichoic acids in the cell walls of the three strains are linked to peptidoglycan through a common linkage saccharide, glucosyl (beta 1----4) N-acetylglucosamine.
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