title: 'Lipoteichoic acid' of Bifidobacterium bifidum subspecies pennsylvanicum DSM 20239. A lipoglycan with monoglycerophosphate side chains.
abstract: The lipid macroamphiphile of Bifidobacterium bifidum subsp. pennsylvanicum DSM 20239 was extracted with phenol/water and purified by treatment with nucleases and hydrophobic interaction chromatography. From analytical data, the results of Smith degradation, hydrolysis with HF and methylation studies, the following structure is proposed: (formula; see text) where n and m are approximately 7-10 and 8-15, respectively. The monoglycerophosphate residues have the sn-glycero-1-phosphate configuration; 20-50% of them are substituted with L-alanine in ester linkage. The lipid anchor is most likely a galactosyldiacylglycerol, part of which carries a third fatty acid. This is the first example among gram-positive bacteria of a glycerophosphate-containing lipid macroamphiphile that carries the glycerophosphate residues as monomeric side chains on a lipoglycan. Further, it contains L-alanine in place of the D-alanine found in lipoteichoic acids.
mesh_terms: D001644:Bifidobacterium / Q000032:analysis*; D055598:Chemical Phenomena; D002621:Chemistry; D005227:Fatty Acids / Q000032:analysis; D005994:Glycerophosphates / Q000302:isolation & purification*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008070:Lipopolysaccharides; D008745:Methylation; D010084:Oxidation-Reduction; D010710:Phosphates / Q000032:analysis; D010712:Phosphatidic Acids / Q000302:isolation & purification*; D011134:Polysaccharides / Q000032:analysis; D013682:Teichoic Acids / Q000302:isolation & purification*
chemical_list: D005227:Fatty Acids; D005994:Glycerophosphates; D008070:Lipopolysaccharides; D010710:Phosphates; D010712:Phosphatidic Acids; D011134:Polysaccharides; D013682:Teichoic Acids; C009900:lipoteichoic acid