Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

Beilstein J Org Chem. 2018 Mar 26:14:697-703. doi: 10.3762/bjoc.14.58. eCollection 2018.

Abstract

The biocatalytic preparation of trans-hex-2-enal from trans-hex-2-enol using a novel aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) is reported. As O2-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O2 in aqueous media and mass transfer limitations resulting in poor reaction rates. These limitations were efficiently overcome by conducting the reaction in a flow-reactor setup reaching unpreceded catalytic activities for the enzyme in terms of turnover frequency (up to 38 s-1) and turnover numbers (more than 300000) pointing towards preparative usefulness of the proposed reaction scheme.

Keywords: alcohol oxidase; alcohol oxidation; aldehyde; flow chemistry.