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Biotechnological production of enantiopure epoxides by enzymatic kinetic resolution


Enantiopure epoxides are high value-added synthons for the production of pharmaceuticals, agrochemicals, as well as versatile fine chemicals and have broad scope of market demand for their applications. A major challenge in conventional organic synthesis is to generate such compounds in high enantiopurity with reasonable yield. Among possible chemical and biological technologies for enantiopure epoxide preparation, enzymatic kinetic resolution has been paid much attention with respect to its high enantioselectivity. Epoxide hydrolase (EH) has shown promising characteristics for the preparation of enantiopure epoxides and vicinal diols during enantioselective hydrolysis of racemic epoxides. EH is readily available from microbial resources thus it is being employed for biohydrolysis of a variety of epoxides. Recent technical progress in EH-catalyzed enantioselective hydrolysis is summarized in terms of exploration of novel EH, its functional improvement, high throughput assay, and preparative scale resolution process.

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This work was supported by Science and Engineering Research Council of A*STAR (Agency for Science, Technology and Research), Singapore.

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Correspondence to Won Jae Choi.

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Choi, W.J. Biotechnological production of enantiopure epoxides by enzymatic kinetic resolution. Appl Microbiol Biotechnol 84, 239–247 (2009).

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  • Enantiopure epoxides
  • Kinetic resolution
  • Epoxide hydrolase
  • Enantioselective hydrolysis