Effect of ionic liquids on epoxide hydrolase-catalyzed synthesis of chiral 1,2-diols

被引:25
作者
Chiappe, Cinzia
Leandri, Elsa
Hammock, Bruce D.
Morisseau, Christophe
机构
[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy
[2] Univ Calif Davis, Dept Entomol, Davis, CA 95616 USA
[3] Univ Calif Davis, Canc Res Ctr, Davis, CA 95616 USA
关键词
D O I
10.1039/b612106c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ionic liquids (ILs) offer new possibilities for epoxide hydrolase (EH) catalyzed resolution of epoxides and for synthesis of chiral 1,2-diols. Soluble EHs from cress and mouse (csEH and msEH) and microsomal EH from rat (rmEH) were tested in several ILs. For all the enzymes tested, higher enantioselectivities were obtained in [bmim][N(Tf)(2)] and [bmim][PF6]. The optimized amount of water for EH activity in these ILs was established. Classical problems arising from low solubility of epoxides in water or from the high tendency of the oxirane ring to undergo chemical hydrolysis were avoided using these new media.
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收藏
页码:162 / 168
页数:7
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