Development of an Enzymatic Process for the Production of (R)-2-Butyl-2-ethyloxirane,Organic Process Research & Development

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Development of an Enzymatic Process for the Production of (R)-2-Butyl-2-ethyloxirane
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2017-07-18 00:00:00 , DOI: 10.1021/acs.oprd.7b00179
Gheorghe-Doru Roiban , Peter W. Sutton , Rebecca Splain , Christopher Morgan , Andrew Fosberry , Katherine Honicker , Paul Homes , Cyril Boudet ₁ , Alison Dann ₁ , Jiasheng Guo , Kristin K. Brown ₂ , Leigh Anne F. Ihnken , Douglas Fuerst

Affiliation

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.

中文翻译：

（R）-2-丁基-2-乙基环氧乙烷生产的酶法开发

环氧化物拆分过程迅速开发了允许访问的多克规模数量（[R）-2-丁基-2-乙基环氧乙烷2使用环氧化物水解酶的易于处理和储存冻干粉末在大于300克/升的反应浓度来源于农杆菌。该酶已成功发酵至35 L规模，并通过下游加工提高了稳定性。卤代醇脱卤素酶也给出了高的对映选择性，但显示出有助于（R）-2环氧化物的水解，而来自黑曲霉的环氧化物水解酶则通过未优化的对映会聚过程提供了（R）-7。

更新日期：2017-07-19

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