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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Veröffentlicht in:Chembiochem : a European journal of chemical biology 2022-03, Vol.23 (6), p.e202200017-n/a
Hauptverfasser: Xu, Xiaomin, Brasselet, Hugo, Jongkind, Ewald P. J., Alcalde, Miguel, Paul, Caroline E., Hollmann, Frank
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container_issue 6
container_start_page e202200017
container_title Chembiochem : a European journal of chemical biology
container_volume 23
creator Xu, Xiaomin
Brasselet, Hugo
Jongkind, Ewald P. J.
Alcalde, Miguel
Paul, Caroline E.
Hollmann, Frank
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. A bienzymatic cascade to access complementary chiral phenylethanols from simple ethylbenzene derivatives is presented, combining peroxygenase‐catalysed oxyfunctionalisation to the corresponding acetophenone with alcohol dehydrogenase‐catalysed enantioselective reduction.
doi_str_mv 10.1002/cbic.202200017
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subjects Alcohol dehydrogenase
Alcohol Dehydrogenase - metabolism
alcohol dehydrogenases
asymmetric reduction
Benzene Derivatives
bienzymatic cascades
Cascade chemical reactions
Dehydrogenase
Dehydrogenases
Enantiomers
Ethylbenzene
Intermediates
Kefir
Ketones
Mixed Function Oxygenases
Oxidation-Reduction
oxyfunctionalisation
peroxygenases
Phenylethyl Alcohol
Rhodococcus
Stereoisomerism
title A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols
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