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

Micro Flow Chemistry and Synthetic Methodology

Research output: Contribution to journal › Article › Academic › 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 O ₂-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O ₂ 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

Bibliographical note

This article is part of the Thematic Series "Integrated multistep flow synthesis". Guest Editor: V. Hessel

Keywords

alcohol oxidase
alcohol oxidation
aldehyde
flow chemistry
Alcohol oxidase
Flow chemistry
Alcohol oxidation
Aldehyde

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10.3762/bjoc.14.58

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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 O 2-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O 2 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, Alcohol oxidase, Flow chemistry, Alcohol oxidation, Aldehyde",

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language = "English",

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T1 - Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

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

AU - Pedroso de Almeida, Tiago

AU - Laudadio, Gabriele

AU - Tieves, Florian

AU - Fernández-Fueyo, Elena

AU - Noël, Timothy

AU - Arends, Isabel W.C.E.

AU - Hollmann, Frank

N1 - This article is part of the Thematic Series "Integrated multistep flow synthesis". Guest Editor: V. Hessel

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 O 2-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O 2 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 O 2-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O 2 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

KW - Alcohol oxidase

KW - Flow chemistry

KW - Alcohol oxidation

KW - Aldehyde

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DO - 10.3762/bjoc.14.58

M3 - Article

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VL - 14

SP - 697

EP - 703

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

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

Abstract

Bibliographical note

Keywords

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