137845-71-7Relevant articles and documents
Gram-Scale Synthesis of Uridine 5'-Diphospho-N-acetylglucosamine: Comparison of Enzymatic and Chemical Routes
Heidlas, Juergen E.,Lees, Watson J.,Pale, Patrick,Whitesides, George M.
, p. 146 - 151 (1992)
Practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N-acetylglucosamine (UDP-GlcNAc) on a gram scale have been developed.The chemoenzymatic synthesis provided convenient access to glucosamine-6-phosphate and N-acetylglucosamine-6-phosphate (GlcNAc-6-P) in > 10 mmol quantities.The condensation between GlcNAc-6-P and UTP was catalyzed by readily available crude enzyme extract from dried cells of the yeast Candida utilis and afforded a 17 percent yield of UDP-GlcNAc from GlcNAc-6-P.The otherwise straightforward chemoenzymatic sequence was hampered by the need to purify the product from the final complex reaction mixture.The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15 percent from pentaacetylglucosamine with the selective formation of tetraacetylglucosamine-α-1-phosphate as the key reaction.