Development of an Enzymatic Process for the Production of (R)‑2-Butyl-2-ethyloxirane

An epoxide resolution process was rapidly developed that allowed access to multigram scale quantities of (R)-2-butyl-2-ethyloxirane 2 at greater than 300 g/L reaction concentration using an easy-to-handle and store lyophilized powder of epoxide hydrolase from Agromyces mediolanus. The enzyme was suc...

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Bibliographic Details
Published in:Organic process research & development 2017-09, Vol.21 (9), p.1302-1310
Main Authors: Roiban, Gheorghe-Doru, Sutton, Peter W, Splain, Rebecca, Morgan, Christopher, Fosberry, Andrew, Honicker, Katherine, Homes, Paul, Boudet, Cyril, Dann, Alison, Guo, Jiasheng, Brown, Kristin K, Ihnken, Leigh Anne F, Fuerst, Douglas
Format: Article
Language:English
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Summary:An epoxide resolution process was rapidly developed that allowed access to multigram scale quantities of (R)-2-butyl-2-ethyloxirane 2 at greater than 300 g/L reaction concentration using an easy-to-handle and store lyophilized powder of epoxide hydrolase from Agromyces mediolanus. The enzyme was successfully fermented on a 35 L scale and stability increased by downstream processing. Halohydrin dehalogenases also gave highly enantioselective resolution but were shown to favor hydrolysis of the (R)-2 epoxide, whereas epoxide hydrolase from Aspergillus niger instead provided (R)-7 via an unoptimized, enantioconvergent process.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.7b00179