op7b00179_si_001.pdf (731.87 kB)
Development of an Enzymatic Process for the Production of (R)‑2-Butyl-2-ethyloxirane
journal contribution
posted on 2017-06-30, 00:00 authored by Gheorghe-Doru Roiban, Peter W. Sutton, Rebecca Splain, Christopher Morgan, Andrew Fosberry, Katherine Honicker, Paul Homes, Cyril Boudet, Alison Dann, Jiasheng Guo, Kristin K. Brown, Leigh Anne F. Ihnken, Douglas FuerstAn
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.