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A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols

In this study, we developed a new bienzymatic reaction to produce enantioenriched phenylethanols. In a first step, the recombinant, unspecific peroxygenase from Agrocybe aegerita (rAaeUPO) was used to oxidise ethylbenzene and its derivatives to the corresponding ketones (prochiral intermediates) fol...

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Autores principales: Xu, Xiaomin, Brasselet, Hugo, Jongkind, Ewald P. J., Alcalde, Miguel, Paul, Caroline E., Hollmann, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9306878/
https://www.ncbi.nlm.nih.gov/pubmed/35023279
http://dx.doi.org/10.1002/cbic.202200017
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author Xu, Xiaomin
Brasselet, Hugo
Jongkind, Ewald P. J.
Alcalde, Miguel
Paul, Caroline E.
Hollmann, Frank
author_facet Xu, Xiaomin
Brasselet, Hugo
Jongkind, Ewald P. J.
Alcalde, Miguel
Paul, Caroline E.
Hollmann, Frank
author_sort Xu, Xiaomin
collection PubMed
description In this study, we developed a new bienzymatic reaction to produce enantioenriched phenylethanols. In a first step, the recombinant, unspecific peroxygenase from Agrocybe aegerita (rAaeUPO) was used to oxidise ethylbenzene and its derivatives to the corresponding ketones (prochiral intermediates) followed by enantioselective reduction into the desired (R)‐ or (S)‐phenylethanols using the (R)‐selective alcohol dehydrogenase (ADH) from Lactobacillus kefir (LkADH) or the (S)‐selective ADH from Rhodococcus ruber (ADH‐A). In a one‐pot two‐step cascade, 11 ethylbenzene derivatives were converted into the corresponding chiral alcohols at acceptable yields and often excellent enantioselectivity.
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spelling pubmed-93068782022-07-28 A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols Xu, Xiaomin Brasselet, Hugo Jongkind, Ewald P. J. Alcalde, Miguel Paul, Caroline E. Hollmann, Frank Chembiochem Research Articles In this study, we developed a new bienzymatic reaction to produce enantioenriched phenylethanols. In a first step, the recombinant, unspecific peroxygenase from Agrocybe aegerita (rAaeUPO) was used to oxidise ethylbenzene and its derivatives to the corresponding ketones (prochiral intermediates) followed by enantioselective reduction into the desired (R)‐ or (S)‐phenylethanols using the (R)‐selective alcohol dehydrogenase (ADH) from Lactobacillus kefir (LkADH) or the (S)‐selective ADH from Rhodococcus ruber (ADH‐A). In a one‐pot two‐step cascade, 11 ethylbenzene derivatives were converted into the corresponding chiral alcohols at acceptable yields and often excellent enantioselectivity. John Wiley and Sons Inc. 2022-01-27 2022-03-18 /pmc/articles/PMC9306878/ /pubmed/35023279 http://dx.doi.org/10.1002/cbic.202200017 Text en © 2022 The Authors. ChemBioChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Xu, Xiaomin
Brasselet, Hugo
Jongkind, Ewald P. J.
Alcalde, Miguel
Paul, Caroline E.
Hollmann, Frank
A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
title A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
title_full A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
title_fullStr A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
title_full_unstemmed A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
title_short A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
title_sort peroxygenase‐alcohol dehydrogenase cascade reaction to transform ethylbenzene derivatives into enantioenriched phenylethanols
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9306878/
https://www.ncbi.nlm.nih.gov/pubmed/35023279
http://dx.doi.org/10.1002/cbic.202200017
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