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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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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. |
format | Online Article Text |
id | pubmed-9306878 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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