Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc.

Li Cai, Wanyi Guan, Wenlan Chen, Peng George Wang

Department of Chemistry, The Ohio State University, 484 West 12th Avenue, Columbus, Ohio 43210, USA.

The Journal of organic chemistry 2010 May 21

filter terms:

2-ketoGlc, which is the C(2)-carbon isostere of GlcNAc, is a novel GlcNAc analogue with a ketone group. The corresponding glycosyltransferase donor substrate, UDP-2-ketoGlc, is necessary for synthesizing 2-ketoGlc-containing molecules and is thus highly important for metabolic polysaccharide remodeling and engineering. We report here the first chemoenzymatic synthesis of UDP-2-ketoGlc using our two-enzyme (NahK and GlmU) system in vitro.

Citation

Li Cai, Wanyi Guan, Wenlan Chen, Peng George Wang. Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc. The Journal of organic chemistry. 2010 May 21;75(10):3492-4