Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases

12 páginas.- 2 figuras.- 2 tablas.- 55 referencias.-Supplementary Materials: The following supporting information can be downloaded at: https:www.mdpi.com/article/10.3390/antiox11030522/s1

Detalles Bibliográficos
Autores: Babot, Esteban Daniel, Aranda, Carmen, Kiebist, Jan, Scheibner, Katrin, Ullrich, René, Hofrichter, Martin, Martínez, Ángel T., Gutiérrez Suárez, Ana
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/264536
Acceso en línea:http://hdl.handle.net/10261/264536
Access Level:acceso abierto
Palabra clave:Epoxidation
Epoxides
Oxyfunctionalization
Peroxygenases
Terminal alkenes
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spelling Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal PeroxygenasesBabot, Esteban DanielAranda, CarmenKiebist, JanScheibner, KatrinUllrich, RenéHofrichter, MartinMartínez, Ángel T.Gutiérrez Suárez, AnaEpoxidationEpoxidesOxyfunctionalizationPeroxygenasesTerminal alkenes12 páginas.- 2 figuras.- 2 tablas.- 55 referencias.-Supplementary Materials: The following supporting information can be downloaded at: https:www.mdpi.com/article/10.3390/antiox11030522/s1Terminal alkenes are among the most attractive starting materials for the synthesis of epoxides, which are essential and versatile intermediate building blocks for the pharmaceutical, fla-voring, and polymer industries. Previous research on alkene epoxidation has focused on the use of several oxidizing agents and/or different enzymes, including cytochrome P450 monooxygenases, as well as microbial whole-cell catalysts that have several drawbacks. Alternatively, we explored the ability of unspecific peroxygenases (UPOs) to selectively epoxidize terminal alkenes. UPOs are attractive biocatalysts because they are robust extracellular enzymes and only require H2O2 as cosub-strate. Here, we show how several UPOs, such as those from Cyclocybe (Agrocybe) aegerita (AaeUPO), Marasmius rotula (MroUPO), Coprinopsis cinerea (rCciUPO), Humicola insolens (rHinUPO), and Daldinia caldariorum (rDcaUPO), are able to catalyze the epoxidation of long-chain terminal alkenes (from C12:1 to C20:1) after an initial optimization of several reaction parameters (cosolvent, cosub-strate, and pH). In addition to terminal epoxides, alkenols and other hydroxylated derivatives of the alkenes were formed. Although all UPOs were able to convert and epoxidize the alkenes, nota-ble differences were observed between them, with rCciUPO being responsible for the highest sub-strate turnover and MroUPO being the most selective with respect to terminal epoxidation. The potential of peroxygenases for epoxidizing long-chain terminal alkenes represents an interesting and green alternative to the existing synthesis technologies. © 2022 by the authors. Licensee MDPI, Basel, SwitzerlandThis research was funded by BioBased Industries Joint Undertaking under the European Union’s Horizon 2020 Research and Innovation Programme, grant number 792063 (SusBind project; https://susbind.eu, accessed on 1 February 2022; to A.G., A.T.M. and M.H.); the PID2020-118968RB-100 project of the Spanish MCIN/AEI/10.13039/501100011033 to A.G.; the CSIC projects PIE-202040E185 (to A.G.) and PIE-202120E019 (to A.T.M.); the CSIC SusPlast platform (to A.T.M.); and the CSIC program for the Spanish Recovery, Transformation and Resilience Plan funded by the Recovery and Resilience Facility of the European Union, established by the Regulation (EU) 2020/2094Peer reviewedMultidisciplinary Digital Publishing InstituteEuropean CommissionMinisterio de Ciencia e Innovación (España)Babot, Esteban Daniel [0000-0001-5539-1721]Aranda, Carmen [0000-0001-8213-1132]Ullrich, René [0000-0002-9165-6341]Hofrichter, Martin [0000-0001-5174-7604]Martínez, Ángel T. [0000-0002-1584-2863]Gutiérrez Suárez, Ana [0000-0002-8823-9029]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202220222022info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/264536reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/EC/H2020/792063PID2020-118968RB-100http://dx.doi.org/10.3390/antiox11030522Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2645362026-05-22T06:33:51Z
dc.title.none.fl_str_mv Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
title Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
spellingShingle Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
Babot, Esteban Daniel
Epoxidation
Epoxides
Oxyfunctionalization
Peroxygenases
Terminal alkenes
title_short Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
title_full Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
title_fullStr Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
title_full_unstemmed Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
title_sort Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal Peroxygenases
dc.creator.none.fl_str_mv Babot, Esteban Daniel
Aranda, Carmen
Kiebist, Jan
Scheibner, Katrin
Ullrich, René
Hofrichter, Martin
Martínez, Ángel T.
Gutiérrez Suárez, Ana
author Babot, Esteban Daniel
author_facet Babot, Esteban Daniel
Aranda, Carmen
Kiebist, Jan
Scheibner, Katrin
Ullrich, René
Hofrichter, Martin
Martínez, Ángel T.
Gutiérrez Suárez, Ana
author_role author
author2 Aranda, Carmen
Kiebist, Jan
Scheibner, Katrin
Ullrich, René
Hofrichter, Martin
Martínez, Ángel T.
Gutiérrez Suárez, Ana
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv European Commission
Ministerio de Ciencia e Innovación (España)
Babot, Esteban Daniel [0000-0001-5539-1721]
Aranda, Carmen [0000-0001-8213-1132]
Ullrich, René [0000-0002-9165-6341]
Hofrichter, Martin [0000-0001-5174-7604]
Martínez, Ángel T. [0000-0002-1584-2863]
Gutiérrez Suárez, Ana [0000-0002-8823-9029]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Epoxidation
Epoxides
Oxyfunctionalization
Peroxygenases
Terminal alkenes
topic Epoxidation
Epoxides
Oxyfunctionalization
Peroxygenases
Terminal alkenes
description 12 páginas.- 2 figuras.- 2 tablas.- 55 referencias.-Supplementary Materials: The following supporting information can be downloaded at: https:www.mdpi.com/article/10.3390/antiox11030522/s1
publishDate 2022
dc.date.none.fl_str_mv 2022
2022
2022
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/10261/264536
url http://hdl.handle.net/10261/264536
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/EC/H2020/792063
PID2020-118968RB-100
http://dx.doi.org/10.3390/antiox11030522
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
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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