Journal of Organic Chemistry p. 146 - 151 (1992)
Update date:2022-08-04
Topics:
Heidlas, Juergen E.
Lees, Watson J.
Pale, Patrick
Whitesides, George M.
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.
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