Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes

Biocatalytic oxidation reactions of toluene derivates to the corresponding aldehydes are typically challenged by regio- and chemoselectivity issues. In this contribution we address both challenges by a combined reactant- and reaction engineering approach. We demonstrate that the peroxygenase-catalys...

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Detalles Bibliográficos
Autores: Wang, Y., Teetz, N., Holtmann, D., Alcalde Galeote, Miguel, van Hengst, J.M.A., Liu, X., Wang, M., Qi, W., Zhang, W., Hollmann, F.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/359632
Acceso en línea:http://hdl.handle.net/10261/359632
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85162015029&doi=10.1002%2fcctc.202300645&partnerID=40&md5=279cf58a5fd578e9379dd48a044145b9
Access Level:acceso abierto
Palabra clave:Benzaldehydes
Biocatalytic oxidation
Peroxygenase
Selective oxyfunctionalisation
Solvent-free biocatalysis
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spelling Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to BenzaldehydesWang, Y.Teetz, N.Holtmann, D.Alcalde Galeote, Miguelvan Hengst, J.M.A.Liu, X.Wang, M.Qi, W.Zhang, W.Hollmann, F.BenzaldehydesBiocatalytic oxidationPeroxygenaseSelective oxyfunctionalisationSolvent-free biocatalysisBiocatalytic oxidation reactions of toluene derivates to the corresponding aldehydes are typically challenged by regio- and chemoselectivity issues. In this contribution we address both challenges by a combined reactant- and reaction engineering approach. We demonstrate that the peroxygenase-catalysed transformation of ring-substituted toluenes proceeds highly regioselectively in benzylic position. Furthermore, neat reaction conditions not only enable attractive product concentrations (up to 185 mM) but also result in highly chemoselective oxidations to the aldehyde level. © 2023 The Authors. ChemCatChem published by Wiley-VCH GmbH.This work was financially supported by the European Research Council (ERC-2021-ADG-101054658) and the China Scholarship Council scholarship for Y.W. (File No.202006250171).Peer reviewedJohn Wiley & SonsEuropean Research CouncilChina Scholarship CouncilConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202420242023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/359632https://www.scopus.com/inward/record.uri?eid=2-s2.0-85162015029&doi=10.1002%2fcctc.202300645&partnerID=40&md5=279cf58a5fd578e9379dd48a044145b9reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/EC/HE/101054658ChemCatChemhttps://doi.org/10.1002/cctc.202300645Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3596322026-05-22T06:33:51Z
dc.title.none.fl_str_mv Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
title Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
spellingShingle Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
Wang, Y.
Benzaldehydes
Biocatalytic oxidation
Peroxygenase
Selective oxyfunctionalisation
Solvent-free biocatalysis
title_short Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
title_full Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
title_fullStr Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
title_full_unstemmed Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
title_sort Selective Peroxygenase-Catalysed Oxidation of Toluene Derivates to Benzaldehydes
dc.creator.none.fl_str_mv Wang, Y.
Teetz, N.
Holtmann, D.
Alcalde Galeote, Miguel
van Hengst, J.M.A.
Liu, X.
Wang, M.
Qi, W.
Zhang, W.
Hollmann, F.
author Wang, Y.
author_facet Wang, Y.
Teetz, N.
Holtmann, D.
Alcalde Galeote, Miguel
van Hengst, J.M.A.
Liu, X.
Wang, M.
Qi, W.
Zhang, W.
Hollmann, F.
author_role author
author2 Teetz, N.
Holtmann, D.
Alcalde Galeote, Miguel
van Hengst, J.M.A.
Liu, X.
Wang, M.
Qi, W.
Zhang, W.
Hollmann, F.
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv European Research Council
China Scholarship Council
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Benzaldehydes
Biocatalytic oxidation
Peroxygenase
Selective oxyfunctionalisation
Solvent-free biocatalysis
topic Benzaldehydes
Biocatalytic oxidation
Peroxygenase
Selective oxyfunctionalisation
Solvent-free biocatalysis
description Biocatalytic oxidation reactions of toluene derivates to the corresponding aldehydes are typically challenged by regio- and chemoselectivity issues. In this contribution we address both challenges by a combined reactant- and reaction engineering approach. We demonstrate that the peroxygenase-catalysed transformation of ring-substituted toluenes proceeds highly regioselectively in benzylic position. Furthermore, neat reaction conditions not only enable attractive product concentrations (up to 185 mM) but also result in highly chemoselective oxidations to the aldehyde level. © 2023 The Authors. ChemCatChem published by Wiley-VCH GmbH.
publishDate 2023
dc.date.none.fl_str_mv 2023
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/359632
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85162015029&doi=10.1002%2fcctc.202300645&partnerID=40&md5=279cf58a5fd578e9379dd48a044145b9
url http://hdl.handle.net/10261/359632
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85162015029&doi=10.1002%2fcctc.202300645&partnerID=40&md5=279cf58a5fd578e9379dd48a044145b9
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/EC/HE/101054658
ChemCatChem
https://doi.org/10.1002/cctc.202300645
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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