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

Autor: 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
Zdroj: Organic Process Research & Development; 20240101, Issue: Preprints
Abstrakt: An epoxide resolution process was rapidly developed that allowed access to multigram scale quantities of (R)-2-butyl-2-ethyloxirane 2at 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)-2epoxide, whereas epoxide hydrolase from Aspergillus nigerinstead provided (R)-7via an unoptimized, enantioconvergent process.
Databáze: Supplemental Index