Teichoic acid from the walls of Staphylococcus aureus H. Structure of the N-acetylglucosaminylribitol residues

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Abstract
Ribitol teichoic acid has been isolated from the walls of Staphylococcus aureus. H, where it accounts for nearly all the organic phosphorus and comprises 25[long dash]40% of the dry weight of the walls. The general structure of this material, which is a ribitol phosphate polymer containing N-acetyl-glucosamine residues and labile D-alanine ester groups, has been confirmed. Alkali hydrolysis followed by phosphatase treatment gives glucosaminylribitol, whereas similar treatment under less vigorous conditions gives N-acetylglucosaminylribitol. Both these glycosides are mixtures of [alpha] and [beta] anomers. The structures (III) and (IV), in which the [alpha]- or [beta]-N-acetylglucosaminyl residue occupies the 4-position of D- ribitol, have been established by periodate oxidation, oxidation and hydrolysis to D-glyceric acid and from optical-rotation studies. Studies with [beta]-N-acetylglucosaminidase confirm the presence of [alpha] and [beta] linkages in the acetylglucosaminides (III) and (IV), and it is concluded that both types of glycosidic linkage occur in teichoic acid preparations from some batches of the organism. The proportion of [alpha] and [beta] linkages in the teichoic acid has varied in samples prepared from different batches of organism, and batches produced recently yield a teichoic acid which apparently does not contain a linkages.