Gram-Scale Synthesis of Uridine 5′-Diphospho-N-acetylglucosamine: Comparison of Enzymic and Chemical Routes Article

Heidlas, JE, Lees, WJ, Pale, P et al. (1992). Gram-Scale Synthesis of Uridine 5′-Diphospho-N-acetylglucosamine: Comparison of Enzymic and Chemical Routes . 57(1), 146-151. 10.1021/jo00027a028



cited authors

  • Heidlas, JE; Lees, WJ; Pale, P; Whitesides, GM

fiu authors

abstract

  • 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 extracts from dried cells of the yeast Candida utilis and afforded a 17% 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% from pentaacetylglucosamine with the selective formation of tetraacetylglucosamine-α-1-phosphate as the key reaction. © 1992, American Chemical Society. All rights reserved.

publication date

  • January 1, 1992

Digital Object Identifier (DOI)

start page

  • 146

end page

  • 151

volume

  • 57

issue

  • 1