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Epoxide Hydrolase-Catalyzed Enantioselective Synthesis of Chiral 1,2-Diols via Desymmetrization of m eso -Epoxides

2004; American Chemical Society; Volume: 126; Issue: 36 Linguagem: Inglês

10.1021/ja0466210

1943-2984

Lishan Zhao, Bin Han, Zilin Huang, Mark A. Miller, Hongjun Huang, Dan S. Malashock, Zuolin Zhu, Aileen Milan, Dan E. Robertson, David P. Weiner, Mark J. Burk,

Microbial Metabolic Engineering and Bioproduction

The discovery, from nature, of a diverse set of microbial epoxide hydrolases is reported. The utility of a library of epoxide hydrolases in the synthesis of chiral 1,2-diols via desymmetrization of a wide range of meso-epoxides, including cyclic as well as acyclic alkyl- and aryl-substituted substrates, is demonstrated. The chiral (R,R)-diols were furnished with high ee's and yields. The discovery of the first microbial epoxide hydrolases providing access to complementary (S,S)-diols is also described.