A SYNTHESIS OF URIDINEDIPHOSPHO-N-ACETYLMURAMIC ACID AND ITS USE AS AN ACCEPTOR OF L-[14C]ALANINE

On the basis of model studies, methyl triacetyl-N-acetylmuramate, largely α form, was treated with H3PO4 under conditions optimal for production of hexosamine-bound phosphate (18% yield). Both anomers were formed but ion exchange failed to separate them. Reaction with uridine 5′-phosphomor-pholidate gave uridinediphospho-N-acetylmuramic acid, isolated in 13% yield; the salt-free product was homogeneous on paper and thin-layer chromatography and exhibited the expected stoichiometry, but in all likelihood is a mixture of the α and β anomers. One-half of the synthetic material serves as an acceptor of [14C]alanine when it is incubated with a cell-free prepa-ration obtained from cultures of group A hemolytic streptococci. The product, uridinediphospho-N-acetylmuramyl-L-alanine, was purified and characterized. © 1968, American Chemical Society. All rights reserved.