title: Characterization of the Streptococcus adjacens group antigen structure.
abstract: Serological classification of bacteria requires the presence of an antigen unique to the organism of interest. Streptococci are serologically differentiated by group antigens, many of which are carbohydrates, although some are amphiphiles. This report describes the chemical characterization of the Streptococcus adjacens group antigen structure. Previous studies demonstrated that the amphiphile contained phosphorus, ribitol, galactose, galactosamine, alanine, and fatty acids. Phosphodiester bonds present in the purified group antigen were identified as part of a poly(ribitol phosphate), since ribitol phosphate was the only organic phosphate detected after acid hydrolysis. Hydrofluoric acid cleavage of the phosphodiester bonds generated oligosaccharide repeating units. Gas chromatography-mass spectrometric analysis of the methylated, acetylated oligosaccharide suggested that the repeating unit is a trisaccharide of Galp beta 1-3Galp beta 1-4GalNac with N-acetylgalactosamine attached in beta-linkage to either the number two or the number four carbon of ribitol. The lipid- and carbohydrate-substituted poly(ribitol phosphate) of the S. adjacens group antigen therefore is a unique amphiphile structure, differing in its repeating-unit structure from the polyglycerophosphate structure of the more common gram-positive amphiphile lipoteichoic acid.
authors.affiliation: Wake Forest University Medical Center, Winston-Salem, North Carolina 27157-1064.
authors.forename: P A
authors.initials: PA
authors.lastname: Sieling
authors.forename: M J
authors.initials: MJ
authors.lastname: Thomas
authors.forename: I
authors.initials: I
authors.lastname: van de Rijn
mesh_terms: D000409:Alanine / Q000737:chemistry; D000942:Antigens, Bacterial / Q000737:chemistry* / Q000187:drug effects; D002236:Carbohydrate Conformation; D002244:Carbon / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D006858:Hydrofluoric Acid / Q000494:pharmacology; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D010504:Periodic Acid / Q000494:pharmacology; D010766:Phosphorylation; D013291:Streptococcus / Q000737:chemistry / Q000145:classification / Q000276:immunology*; D013329:Structure-Activity Relationship
chemical_list: D000942:Antigens, Bacterial; D005227:Fatty Acids; D010504:Periodic Acid; D002244:Carbon; D000409:Alanine; D006858:Hydrofluoric Acid