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.
KeywordsUridine Diphosphate Lithium Salt Lithium Hydroxide Polar Peak Muramic Acid
Unable to display preview. Download preview PDF.
- Liger, D., Blanot, D. and van Heijenoort, J. (1991) Effect of various alanine analogues on the L-alanine-adding enzyme from Escherichia coli. FEMS Microbiol. Lett. 80, 111–116.Google Scholar
- Michaud, C., Mengin-Lecreulx, D., van Heijenoort, J. and Blanot, D. (1990) Over-production, purification and properties of the uridine-diphosphate-N-acetylmuramoyl-L-alanyl-D-glutamate: jneso-2, 6-diaminopimelate ligase from Escherichia coli. Eur. J. Biochem. 194, 853–861.PubMedCrossRefGoogle Scholar
- Osawa, T. and Jeanloz, R.W. (1965 b) The synthesis of a 2-amino-2-deoxy-D-glucosyl-muramic acid disaccharide: 2-acetamido-6-0-(2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-3-D-glucopyranosyl)-1, 4-di-0-acetyl-2-deoxy-3-0-[D-l-(methyl carboxylate)ethyl]-a-D-glucopyranose. Carbohydr. Res. 1, 181–186.CrossRefGoogle Scholar
- Roseman, S., Distler, J.J., Moffatt, J.G. and Khorana, H.G. (1961) Nucleoside polyphosphates. XI. An improved general method for the synthesis of nucleotide coenzymes. Syntheses of uridine-5′, cytidine-5′ and guanosine-5′ diphosphate derivatives. J. Amer. Chem. Soc. 83, 659–663.CrossRefGoogle Scholar