Using ionic liquids to improve Novozym 435-catalayzed regioselective acylation of 1–b–D–arabinofuranosylcytosine

I&EC 120

Xiao-feng Li, xflibio@scut.edu.cn1, Min-hua Zong, btmhzong@scut.edu.cn2, and Ru-de Yang, yangrd@scut.edu.cn2. (1) College of light industry and food sciences, South China University of Technology, 381 Wushan Street, Guangzhou, 510640, China, (2) College of Biological Sciences and Biotechnology, South China University of Technology, 1 Wushan Street, Guangzhou, 510640, China
Seven ionic liquids (ILs) were tested for their potential in Novozym 435-catalyzed regioselective acylation of 1-b-D-arabinofuranosylcytosine with vinyl propionate. The results demonstrate that BMIM·PF6/THF co-solvent can markedly boost the reaction rate and substrate conversion. To better understand the reaction performed in IL-containing systems, various influential variables were examined. The optimal IL concentration, initial water activity, enzyme dosage, molar ratio of 1-b-D-arabinofuranosylcytosine to vinyl propionate, and reaction temperature were found to be 10% (v/v), 0.07, 500U/ml, 1:15, and 60°C, respectively, under which the initial reaction rate, maximum substrate conversion and regioselectivity were 96.0mM/h, 96.0% and 99%, which are much higher than those achieved in typical organic solvents. It was also observed that the lipase exhibited higher stability in 10% (v/v) BMIM·PF6/THF mixture than in other solvents assayed. This study represents the first attempt to prepare 5′-O-monoester of 1-b-D-arabinofuranosylcytosine via enzymatic acylation in IL-containing systems.
 

Ionic Liquids: Not Just Solvents Anymore OR Ionic Liquids: Parallel Futures (Sponsored by Green Chemistry and Engineering, Separation Science and Technology and Novel Chemistry with Industrial Applications Sub-Divisions)
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Industrial and Engineering Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006