The Synthesis of Teichoic Acids

In the two preceding papers, evidence has been presented for the enzymatic synthesis of polyglycerophosphate (1) and polyribitol phosphate (2) from cytidine diphosphate glycerol and cytidine diphosphate ribitol, respectively. In this paper, we describe the glycosyl transfer from uridine diphosphate glucose to polyglycerophosphate by an enzyme from Bacillus subtilis. Teichoic acids differ in the nature and number of the glycosyl residues attached to the polyol phosphate backbone (3). The glucosyl transfer described in this paper gives rise to one of the simplest teichoic acid structures, in which every glycerol residue in the polyglycerophosphate backbone has attached to the hydroxyl at carbon 2 an ol-glucopyranosyl residue. A similar reaction, the transfer of N-acetylglucosamine residues to polyribitol phosphate from UDP-N-acetylglucosamine has been described by Nathenson and Strominger (4). A second glucosylating system for glycerol teichoic acid has been described in a preliminary communication (5). This system isolated from BaciUus Zicheniformis is more complex and will be reported in detail later.