N-acetylmannosaminyl(1----4)N-acetylglucosamine, a linkage unit between glycerol teichoic acid and peptidoglycan in cell walls of several Bacillus strains.
The structure of teichoic acid-glycopeptide complexes isolated from lysozyme digests of cell walls of Bacillus subtilis (four strains) and Bacillus licheniformis (one strain) was studied to obtain information on the structural relationship between glycerol teichoic acids and their linkage saccharides. Each preparation of the complexes contained equimolar amounts of muramic acid 6-phosphate and mannosamine in addition to glycopeptide components and glycerol teichoic acid components characteristic of the strain. Upon treatment with 47% hydrogen fluoride, these preparations gave, in common, a hexosamine-containing disaccharide, which was identified as N- acetylmannosaminyl (1----4) N-acetylglucosamine, along with large amounts of glycosylglycerols presumed to be the dephosphorylated repeating units of teichoic acid chains. The glycosylglycerol obtained from each bacterial strain was identified as follows: B. subtilis AHU 1392, glucosyl alpha (1----2)glycerol; B. subtilis AHU 1235, glucosyl beta(1----2) glycerol; B. subtilis AHU 1035 and AHU 1037, glucosyl alpha (1----6)galactosyl alpha (1----1 or 3)glycerol; B. licheniformis AHU 1371, galactosyl alpha (1----2)glycerol. By means of Smith degradation, the galactose residues in the teichoic acid-glycopeptide complexes from B. subtilis AHU 1035 and AHU 1037 and B. licheniformis AHU 1371 were shown to be involved in the backbone chains of the teichoic acid moieties. Thus, the glycerol teichoic acids in the cell walls of five bacterial strains seem to be joined to peptidoglycan through a common linkage disaccharide, N- acetylmannosaminyl (1----4)N-acetylglucosamine, irrespective of the structural diversity in the glycosidic branches and backbone chains.
D000117:Acetylglucosamine / Q000032:analysis*; D001407:Bacillus / Q000032:analysis*; D001412:Bacillus subtilis / Q000032:analysis*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002473:Cell Wall / Q000032:analysis*; D055598:Chemical Phenomena; D002621:Chemistry; D004187:Disaccharides / Q000032:analysis*; D005944:Glucosamine / Q000031:analogs & derivatives*; D006595:Hexosamines / Q000032:analysis*; D008745:Methylation; D010457:Peptidoglycan / Q000032:analysis*; D013045:Species Specificity; D013682:Teichoic Acids / Q000032:analysis*
D004187:Disaccharides; D006595:Hexosamines; C027063:N-acetylmannosaminyl(1-4)N-acetylglucosamine; D010457:Peptidoglycan; D013682:Teichoic Acids; D005944:Glucosamine; D000117:Acetylglucosamine; C002022:N-acetylmannosamine