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 |
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| 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 |
| format | Article |
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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.</description><identifier>ISSN: 1439-4227</identifier><identifier>ISSN: 1439-7633</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.202200017</identifier><identifier>PMID: 35023279</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>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</subject><ispartof>Chembiochem : a European journal of chemical biology, 2022-03, Vol.23 (6), p.e202200017-n/a</ispartof><rights>2022 The Authors. ChemBioChem published by Wiley-VCH GmbH</rights><rights>2022 The Authors. ChemBioChem published by Wiley-VCH GmbH.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4687-951271841d89d92bb9bdba0eebc3fd978dc9d5764fe2632470ddc39960ca8eda3</citedby><cites>FETCH-LOGICAL-c4687-951271841d89d92bb9bdba0eebc3fd978dc9d5764fe2632470ddc39960ca8eda3</cites><orcidid>0000-0002-5409-0211 ; 0000-0003-4506-5556 ; 0000-0003-4821-756X ; 0000-0001-6780-7616 ; 0000-0002-7889-9920 ; 0000-0002-5256-4479</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbic.202200017$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbic.202200017$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,782,786,887,1419,27931,27932,45581,45582</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35023279$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xu, Xiaomin</creatorcontrib><creatorcontrib>Brasselet, Hugo</creatorcontrib><creatorcontrib>Jongkind, Ewald P. J.</creatorcontrib><creatorcontrib>Alcalde, Miguel</creatorcontrib><creatorcontrib>Paul, Caroline E.</creatorcontrib><creatorcontrib>Hollmann, Frank</creatorcontrib><title>A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>Chembiochem</addtitle><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.</description><subject>Alcohol dehydrogenase</subject><subject>Alcohol Dehydrogenase - metabolism</subject><subject>alcohol dehydrogenases</subject><subject>asymmetric reduction</subject><subject>Benzene Derivatives</subject><subject>bienzymatic cascades</subject><subject>Cascade chemical reactions</subject><subject>Dehydrogenase</subject><subject>Dehydrogenases</subject><subject>Enantiomers</subject><subject>Ethylbenzene</subject><subject>Intermediates</subject><subject>Kefir</subject><subject>Ketones</subject><subject>Mixed Function Oxygenases</subject><subject>Oxidation-Reduction</subject><subject>oxyfunctionalisation</subject><subject>peroxygenases</subject><subject>Phenylethyl Alcohol</subject><subject>Rhodococcus</subject><subject>Stereoisomerism</subject><issn>1439-4227</issn><issn>1439-7633</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>EIF</sourceid><recordid>eNqFkc1uEzEURkcIREthyxJZYsMmwT8Te7xBCkOASpVaobK2PPadjivHLvYkMKzgDXhGngRXCSmwYWXLPt_Rvfqq6inBc4IxfWk6Z-YUU4oxJuJedUxqJmeCM3Z_f68pFUfVo5yvCyI5Iw-rI7bAlFEhj6vvS3QBKX6ZriDoDD-__Vh6E4fo0RsYJpvi7h21OhttAX0AbUYXAxojukw65D6mNVqNw-Q7CF8hQAkmt9Wj20JGLhRuFXQoGQjJmQEsuhggTB7GQYfo8-PqQa99hif786T6-HZ12b6fnZ2_O22XZzNT80bM5IJQQZqa2EZaSbtOdrbTGKAzrLdSNNZIuxC87oFyRmuBrTVMSo6NbsBqdlK92nlvNt0arIEwJu3VTXJrnSYVtVN__wQ3qKu4VZLhMkBTBC_2ghQ_bSCPau2yAe91gLjJinIiF0w2VBT0-T_oddykUNYrVI1rwXnDCjXfUSbFnBP0h2EIVrftqtt21aHdEnj25woH_HedBZA74LPzMP1Hp9rXp-2d_BdHlbYX</recordid><startdate>20220318</startdate><enddate>20220318</enddate><creator>Xu, Xiaomin</creator><creator>Brasselet, Hugo</creator><creator>Jongkind, Ewald P. 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J. ; Alcalde, Miguel ; Paul, Caroline E. ; Hollmann, Frank</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4687-951271841d89d92bb9bdba0eebc3fd978dc9d5764fe2632470ddc39960ca8eda3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alcohol dehydrogenase</topic><topic>Alcohol Dehydrogenase - metabolism</topic><topic>alcohol dehydrogenases</topic><topic>asymmetric reduction</topic><topic>Benzene Derivatives</topic><topic>bienzymatic cascades</topic><topic>Cascade chemical reactions</topic><topic>Dehydrogenase</topic><topic>Dehydrogenases</topic><topic>Enantiomers</topic><topic>Ethylbenzene</topic><topic>Intermediates</topic><topic>Kefir</topic><topic>Ketones</topic><topic>Mixed Function Oxygenases</topic><topic>Oxidation-Reduction</topic><topic>oxyfunctionalisation</topic><topic>peroxygenases</topic><topic>Phenylethyl Alcohol</topic><topic>Rhodococcus</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Xiaomin</creatorcontrib><creatorcontrib>Brasselet, Hugo</creatorcontrib><creatorcontrib>Jongkind, Ewald P. 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J.</au><au>Alcalde, Miguel</au><au>Paul, Caroline E.</au><au>Hollmann, Frank</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Peroxygenase‐Alcohol Dehydrogenase Cascade Reaction to Transform Ethylbenzene Derivatives into Enantioenriched Phenylethanols</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>Chembiochem</addtitle><date>2022-03-18</date><risdate>2022</risdate><volume>23</volume><issue>6</issue><spage>e202200017</spage><epage>n/a</epage><pages>e202200017-n/a</pages><issn>1439-4227</issn><issn>1439-7633</issn><eissn>1439-7633</eissn><abstract>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.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35023279</pmid><doi>10.1002/cbic.202200017</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-5409-0211</orcidid><orcidid>https://orcid.org/0000-0003-4506-5556</orcidid><orcidid>https://orcid.org/0000-0003-4821-756X</orcidid><orcidid>https://orcid.org/0000-0001-6780-7616</orcidid><orcidid>https://orcid.org/0000-0002-7889-9920</orcidid><orcidid>https://orcid.org/0000-0002-5256-4479</orcidid><oa>free_for_read</oa></addata></record> |
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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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