Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase
Exploiting catalytic promiscuity: The proline‐based enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes asymmetric Michael‐type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans‐β‐nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4‐OT effected for...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2013-01, Vol.14 (2), p.191-194 |
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| container_title | Chembiochem : a European journal of chemical biology |
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| creator | Miao, Yufeng Geertsema, Edzard M. Tepper, Pieter G. Zandvoort, Ellen Poelarends, Gerrit J. |
| description | Exploiting catalytic promiscuity: The proline‐based enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes asymmetric Michael‐type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans‐β‐nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4‐OT effected formation of the anticipated γ‐nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %. |
| doi_str_mv | 10.1002/cbic.201200676 |
| format | Article |
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KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3836-9a24461fa5ad079240944a445eac60d0eefa57c5b8bc9750cfb7149453d6257a3</citedby><cites>FETCH-LOGICAL-c3836-9a24461fa5ad079240944a445eac60d0eefa57c5b8bc9750cfb7149453d6257a3</cites></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.201200676$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbic.201200676$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23303727$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miao, Yufeng</creatorcontrib><creatorcontrib>Geertsema, Edzard M.</creatorcontrib><creatorcontrib>Tepper, Pieter G.</creatorcontrib><creatorcontrib>Zandvoort, Ellen</creatorcontrib><creatorcontrib>Poelarends, Gerrit J.</creatorcontrib><title>Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>ChemBioChem</addtitle><description>Exploiting catalytic promiscuity: The proline‐based enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes asymmetric Michael‐type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans‐β‐nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4‐OT effected formation of the anticipated γ‐nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %.</description><subject>Aldehydes - chemistry</subject><subject>Aldehydes - metabolism</subject><subject>biocatalysis</subject><subject>Catalysis</subject><subject>catalytic promiscuity</subject><subject>Isomerases - chemistry</subject><subject>Isomerases - metabolism</subject><subject>Michael addition</subject><subject>Models, Molecular</subject><subject>nitroaldehydes</subject><subject>Proline - chemistry</subject><subject>Proline - metabolism</subject><subject>Styrenes - chemistry</subject><subject>Styrenes - metabolism</subject><subject>tautomerases</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAURSMEoqWwZYm8ZOPBsR27WU6iUiqFlsWgSmwsx3nRGJJ4sB3R8Cl8Bh_CN-FhhhE7Vn6Sz73v6d4se5mTVU4IfWNaa1aU5JQQIcWj7DznrMRSMPb4OHNK5Vn2LITPhJBSsPxpdkYZI0xSeZ79-ODdaIOZ3RxQraMelmADcj1ah2UcIXpr0HtrthoGvFl2gNZdZ6N10x-osRNoj9ZDB9ulg4CiQ79-4lsbvQtx8TABahcUt4DSoiHRuNIBOnQ1fV9GQBzfPejBGe-im3QEtNFzdCP4BD3PnvR6CPDi-F5kH99ebep3uLm7vqnXDTbskglcasq5yHtd6I7IknJScq45L0AbQToCkL6kKdrL1pSyIKZvZc5LXrBO0EJqdpG9PvjuvPs6Q4hqHwgMg54gpaJyKplgPGWW0NUBTQeH4KFXO29H7ReVE7XvQ-37UKc-kuDV0XtuR-hO-N8CElAegG92gOU_dqqubup_zfFBa0OEh5NW-y9KSCYLdX97rZqqaspPpFL37DeGvKlf</recordid><startdate>20130121</startdate><enddate>20130121</enddate><creator>Miao, Yufeng</creator><creator>Geertsema, Edzard M.</creator><creator>Tepper, Pieter G.</creator><creator>Zandvoort, Ellen</creator><creator>Poelarends, Gerrit J.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130121</creationdate><title>Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase</title><author>Miao, Yufeng ; Geertsema, Edzard M. ; Tepper, Pieter G. ; Zandvoort, Ellen ; Poelarends, Gerrit J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3836-9a24461fa5ad079240944a445eac60d0eefa57c5b8bc9750cfb7149453d6257a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aldehydes - chemistry</topic><topic>Aldehydes - metabolism</topic><topic>biocatalysis</topic><topic>Catalysis</topic><topic>catalytic promiscuity</topic><topic>Isomerases - chemistry</topic><topic>Isomerases - metabolism</topic><topic>Michael addition</topic><topic>Models, Molecular</topic><topic>nitroaldehydes</topic><topic>Proline - chemistry</topic><topic>Proline - metabolism</topic><topic>Styrenes - chemistry</topic><topic>Styrenes - metabolism</topic><topic>tautomerases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miao, Yufeng</creatorcontrib><creatorcontrib>Geertsema, Edzard M.</creatorcontrib><creatorcontrib>Tepper, Pieter G.</creatorcontrib><creatorcontrib>Zandvoort, Ellen</creatorcontrib><creatorcontrib>Poelarends, Gerrit J.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miao, Yufeng</au><au>Geertsema, Edzard M.</au><au>Tepper, Pieter G.</au><au>Zandvoort, Ellen</au><au>Poelarends, Gerrit J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>ChemBioChem</addtitle><date>2013-01-21</date><risdate>2013</risdate><volume>14</volume><issue>2</issue><spage>191</spage><epage>194</epage><pages>191-194</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>Exploiting catalytic promiscuity: The proline‐based enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes asymmetric Michael‐type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans‐β‐nitrostyrene in aqueous solvent. 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| fulltext | fulltext |
| identifier | ISSN: 1439-4227 |
| ispartof | Chembiochem : a European journal of chemical biology, 2013-01, Vol.14 (2), p.191-194 |
| issn | 1439-4227 1439-7633 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Aldehydes - chemistry Aldehydes - metabolism biocatalysis Catalysis catalytic promiscuity Isomerases - chemistry Isomerases - metabolism Michael addition Models, Molecular nitroaldehydes Proline - chemistry Proline - metabolism Styrenes - chemistry Styrenes - metabolism tautomerases |
| title | Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase |
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