Issue 2, 2007
From the journal:

Green Chemistry

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

Cinzia Chiappe,*a   Elsa Leandri,a   Bruce D. Hammock*b  and  Christophe Morisseaub  

* Corresponding authors

a Dipartimento di Chimica Bioorganica e Biofarmacia, via Bonanno 33, Pisa, Italy
E-mail: cinziac@farm.unipi.it
Fax: +39 50 2219660
Tel: +39 50 2219669

b Department of Entomology & Cancer Research Center, University of California, Davis, CA, USA
E-mail: bdhammock@ucdavis.edu

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/B612106C
Article type
Paper
Submitted
22 Aug 2006
Accepted
30 Oct 2006
First published
14 Nov 2006

Green Chem., 2007,9, 162-168

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

C. Chiappe, E. Leandri, B. D. Hammock and C. Morisseau, Green Chem., 2007, 9, 162 DOI: 10.1039/B612106C

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