Synthesis of α and β anomers of UDP-N-acetylmuramic acid☆

UDP-N-acetylmuramyl (UDP-MurNAc) derivatives are substrates for several cytoplasmics steps of the synthesis of bacterial peptidoglycan (Park, 1952). Their availability is a prerequisite for developing the detailed study of the synthetases catalyzing these reactions. Since they are not commercial compounds, they have to be prepared from bacterial cells in which they accumulate under specific conditions. However, such procedures are long and tedious, and yields are often low. An alternative approach is to chemically synthesize UDP-N-acetylmuramic acid on a large scale, and to use it as starting material for the in vitro enzymatic preparation of the other UDP-MurNAc precursors. In this communication, we wish to report the total synthesis of UDP-MurNAc.