Anomeric configuration of N-acetylglucosaminyl phosphorylundecaprenols formed in Bacillus cereus Membranes.

The structural difference was studied between two N-acetylglucosaminyl phosphorylundecaprenols formed by incubation of Bacillus cereus membranes with UDP-N-acetylglucosamine. On the treatment with 50% phenol, the major one of these glycolipids (Lipid 1) yielded a saccharide phosphate, while the other (Lipid 2) yielded N-acetylglucosamine along with a saccharide phosphate. The saccharide phosphates from Lipids 1 and 2 were identified as alpha-N-acetylglucosamine 1-phosphate and its beta-anomer, respectively, based on their susceptibility to acid, alpha- and beta-N-acetylglucosaminidases, and UDP-N-acetylglucosamine pyrophosphorylase. Thus, it seems most probable that Lipids 1 and 2 were alpha- and beta-N-acetylglucosaminyl phosphorylundecaprenols, respectively.