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

Morten M.C.H. Van Schie; Tiago Pedroso De Almeida; Gabriele Laudadio; Florian Tieves; Elena Fernández-Fueyo; Timothy Noël; Isabel W.C.E. Arends; Frank Hollmann

doi:10.3762/bjoc.14.58

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

Morten M.C.H. Van Schie, Tiago Pedroso De Almeida, Gabriele Laudadio, Florian Tieves, Elena Fernández-Fueyo, Timothy Noël^*, Isabel W.C.E. Arends, Frank Hollmann

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

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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.

Original language	English
Pages (from-to)	697-703
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	14
DOIs	https://doi.org/10.3762/bjoc.14.58
Publication status	Published - 26 Mar 2018

Keywords

Alcohol oxidase
Alcohol oxidation
Aldehyde
Flow chemistry

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10.3762/bjoc.14.58

1860-5397-14-58-1Final published version, 258 KB

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title = "Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor",

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",

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doi = "10.3762/bjoc.14.58",

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AU - Van Schie, Morten M.C.H.

AU - De Almeida, Tiago Pedroso

AU - Laudadio, Gabriele

AU - Tieves, Florian

AU - Fernández-Fueyo, Elena

AU - Noël, Timothy

AU - Arends, Isabel W.C.E.

AU - Hollmann, Frank

PY - 2018/3/26

Y1 - 2018/3/26

N2 - 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.

AB - 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.

KW - Alcohol oxidase

KW - Alcohol oxidation

KW - Aldehyde

KW - Flow chemistry

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M3 - Article

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SN - 1860-5397

VL - 14

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EP - 703

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Keywords

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