Gram-Scale Synthesis of Uridine 5'-Diphospho-N-acetylglucosamine: Comparison of Enzymatic and Chemical Routesr

practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N'acetylglucosamine (UDP-GlcNAc) on r !ruscale have been developed. The chemoenzymatic synthesis provided convenient access to glucosaminigpnosphate and N-acetylgluiosamine&phosphatc (GlcNAc-GP) in )lGmmol quantities. The condensation betweenblcNAc-6-P and UTi, was catalyzed by readily available crude enzyme extracts from dried cells of the ieit Co"aida utitis and afforde d a LTVo yield of UDP-GlcNAc from GlcNAc-6-P. The otherwise straightforward .h.-*n y-"tic sequence was hampered by the need to punfy the product from the final complex reaction mixture. The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15% from pentaacetvlgluco."-i.,. with the selective formation of tetraacetylglucosamine-a-1-phosphate as the key reaction.