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

Abstract

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.

Scandium‐Bipyridine‐Catalyzed, Enantioselective Alcoholysis of meso‐Epoxides

“…Flash column chromatography was performed by using Merck silica gel 60 230-400 mesh (0.040-0.063 mm). (Z)-1,2-Bis(naphthalen-2-yl)ethene, [19] (Z)-1,2-di-m-tolylethene, [19] cis-1,2-bis(p-chlorophenyl)ethane oxide [20] and 1,4-dimethylidene-2,3-epoxy-2,3-dihydronaphthalene [10e] were prepared according to litera-ture procedures. Epoxides 13-14, 24 and 26-27 were prepared by m-CPBA oxidation of the corresponding cis-alkenes.…”

Catalytic, enantioselective synthesis of Boc-protected 1,2-amino alcohols through aminolysis of meso-epoxides with benzophenone imine

“…Flash column chromatography was performed by using Merck silica gel 60 230-400 mesh. The meso-epoxides 3b and 3c were prepared according to the method of Burk et al 18 The chiral bipyridine was best prepared according to the protocol developed by Kobayashi. 19 All other chemicals were used as received from commercial suppliers.…”

Novel genes retrieved from environmental DNA by polymerase chain reaction: Current genome-walking techniques for future metagenome applications

“…A concerted screening approach based on enzymatic activity and sequence homology led to the identification of eDNA-derived genes coding for epoxide hydrolases, and ␣-amylases (Zhao et al, 2004;Richardson et al, 2002). The sequence-specific discovery or enrichment was carried out using library DNA and labelled probes in a high-throughput hybridization-based format.…”