Photo‐biocatalytic One‐Pot Cascades for the Enantioselective Synthesis of 1,3‐Mercaptoalkanol Volatile Sulfur Compounds
The synthesis of enantiomerically pure 1,3‐mercaptoalkanol volatile sulfur compounds through a one‐pot photo‐biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient on a wide range of substrates. The one‐pot ca...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-05, Vol.57 (20), p.5803-5807 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Lauder, Kate Toscani, Anita Qi, Yuyin Lim, Jesmine Charnock, Simon J. Korah, Krupa Castagnolo, Daniele |
| description | The synthesis of enantiomerically pure 1,3‐mercaptoalkanol volatile sulfur compounds through a one‐pot photo‐biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient on a wide range of substrates. The one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium provides a green and sustainable approach to enantiomerically pure 1,3‐mercaptoalkanols in high yields with excellent enantioselectivity.
A dependable route to volatile products: A one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium was developed for the synthesis of enantiomerically pure 1,3‐mercaptoalkanols (see scheme). Two new ketoreductase (KRED) biocatalysts with opposite enantioselectivity were discovered and found to reduce a wide range of substrates efficiently. |
| doi_str_mv | 10.1002/anie.201802135 |
| format | Article |
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A dependable route to volatile products: A one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium was developed for the synthesis of enantiomerically pure 1,3‐mercaptoalkanols (see scheme). Two new ketoreductase (KRED) biocatalysts with opposite enantioselectivity were discovered and found to reduce a wide range of substrates efficiently.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201802135</identifier><identifier>PMID: 29533509</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>biocatalysis ; Biocatalysts ; Cascade chemical reactions ; Enantiomers ; ketoreductases ; mercaptoalkanols ; photocatalysis ; Substrates ; Sulfur ; Sulfur compounds ; Synthesis ; volatile sulfur compounds</subject><ispartof>Angewandte Chemie International Edition, 2018-05, Vol.57 (20), p.5803-5807</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4505-b8be85a3dd31ef6d9865d88076c04c33ff5fdaacaec939c8a92a4e83d25a1ae43</citedby><cites>FETCH-LOGICAL-c4505-b8be85a3dd31ef6d9865d88076c04c33ff5fdaacaec939c8a92a4e83d25a1ae43</cites><orcidid>0000-0002-7517-5732</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%2Fanie.201802135$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201802135$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29533509$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lauder, Kate</creatorcontrib><creatorcontrib>Toscani, Anita</creatorcontrib><creatorcontrib>Qi, Yuyin</creatorcontrib><creatorcontrib>Lim, Jesmine</creatorcontrib><creatorcontrib>Charnock, Simon J.</creatorcontrib><creatorcontrib>Korah, Krupa</creatorcontrib><creatorcontrib>Castagnolo, Daniele</creatorcontrib><title>Photo‐biocatalytic One‐Pot Cascades for the Enantioselective Synthesis of 1,3‐Mercaptoalkanol Volatile Sulfur Compounds</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The synthesis of enantiomerically pure 1,3‐mercaptoalkanol volatile sulfur compounds through a one‐pot photo‐biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient on a wide range of substrates. The one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium provides a green and sustainable approach to enantiomerically pure 1,3‐mercaptoalkanols in high yields with excellent enantioselectivity.
A dependable route to volatile products: A one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium was developed for the synthesis of enantiomerically pure 1,3‐mercaptoalkanols (see scheme). Two new ketoreductase (KRED) biocatalysts with opposite enantioselectivity were discovered and found to reduce a wide range of substrates efficiently.</description><subject>biocatalysis</subject><subject>Biocatalysts</subject><subject>Cascade chemical reactions</subject><subject>Enantiomers</subject><subject>ketoreductases</subject><subject>mercaptoalkanols</subject><subject>photocatalysis</subject><subject>Substrates</subject><subject>Sulfur</subject><subject>Sulfur compounds</subject><subject>Synthesis</subject><subject>volatile sulfur compounds</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkU2LFDEQhoMo7rp69SgBL3uwx3x0utPHZRh1YXUX_Lg2NUmFzZpJxk5amYPgT_A3-kvMMOsKXjxVUTz1UvW-hDzlbMEZEy8helwIxjUTXKp75JgrwRvZ9_J-7Vspm14rfkQe5XxTea1Z95AciUFJqdhwTL5fXaeSfv34ufbJQIGwK97Qy4h1dJUKXUI2YDFTlyZarpGuIsTiU8aApvivSN_vYp1nn2lylL-QdfEtTga2JUH4DDEF-ikFKD5Udg5unugybbZpjjY_Jg8chIxPbusJ-fhq9WH5prm4fH2-PLtoTKuYatZ6jVqBtFZydJ0ddKdsfaXvDGuNlM4pZwEMoBnkYDQMAlrU0goFHLCVJ-T0oLud0pcZcxk3PhsMASKmOY_VQKl4p1tV0ef_oDdpnmK9rlJSiV6wfk8tDpSZUs4TunE7-Q1Mu5GzcR_MuA9mvAumLjy7lZ3XG7R3-J8kKjAcgG_VqN1_5Mazd-erv-K_Af0Vnts</recordid><startdate>20180514</startdate><enddate>20180514</enddate><creator>Lauder, Kate</creator><creator>Toscani, Anita</creator><creator>Qi, Yuyin</creator><creator>Lim, Jesmine</creator><creator>Charnock, Simon J.</creator><creator>Korah, Krupa</creator><creator>Castagnolo, Daniele</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7517-5732</orcidid></search><sort><creationdate>20180514</creationdate><title>Photo‐biocatalytic One‐Pot Cascades for the Enantioselective Synthesis of 1,3‐Mercaptoalkanol Volatile Sulfur Compounds</title><author>Lauder, Kate ; Toscani, Anita ; Qi, Yuyin ; Lim, Jesmine ; Charnock, Simon J. ; Korah, Krupa ; Castagnolo, Daniele</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4505-b8be85a3dd31ef6d9865d88076c04c33ff5fdaacaec939c8a92a4e83d25a1ae43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>biocatalysis</topic><topic>Biocatalysts</topic><topic>Cascade chemical reactions</topic><topic>Enantiomers</topic><topic>ketoreductases</topic><topic>mercaptoalkanols</topic><topic>photocatalysis</topic><topic>Substrates</topic><topic>Sulfur</topic><topic>Sulfur compounds</topic><topic>Synthesis</topic><topic>volatile sulfur compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lauder, Kate</creatorcontrib><creatorcontrib>Toscani, Anita</creatorcontrib><creatorcontrib>Qi, Yuyin</creatorcontrib><creatorcontrib>Lim, Jesmine</creatorcontrib><creatorcontrib>Charnock, Simon J.</creatorcontrib><creatorcontrib>Korah, Krupa</creatorcontrib><creatorcontrib>Castagnolo, Daniele</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lauder, Kate</au><au>Toscani, Anita</au><au>Qi, Yuyin</au><au>Lim, Jesmine</au><au>Charnock, Simon J.</au><au>Korah, Krupa</au><au>Castagnolo, Daniele</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photo‐biocatalytic One‐Pot Cascades for the Enantioselective Synthesis of 1,3‐Mercaptoalkanol Volatile Sulfur Compounds</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-05-14</date><risdate>2018</risdate><volume>57</volume><issue>20</issue><spage>5803</spage><epage>5807</epage><pages>5803-5807</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The synthesis of enantiomerically pure 1,3‐mercaptoalkanol volatile sulfur compounds through a one‐pot photo‐biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient on a wide range of substrates. The one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium provides a green and sustainable approach to enantiomerically pure 1,3‐mercaptoalkanols in high yields with excellent enantioselectivity.
A dependable route to volatile products: A one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium was developed for the synthesis of enantiomerically pure 1,3‐mercaptoalkanols (see scheme). Two new ketoreductase (KRED) biocatalysts with opposite enantioselectivity were discovered and found to reduce a wide range of substrates efficiently.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29533509</pmid><doi>10.1002/anie.201802135</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-7517-5732</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | biocatalysis Biocatalysts Cascade chemical reactions Enantiomers ketoreductases mercaptoalkanols photocatalysis Substrates Sulfur Sulfur compounds Synthesis volatile sulfur compounds |
| title | Photo‐biocatalytic One‐Pot Cascades for the Enantioselective Synthesis of 1,3‐Mercaptoalkanol Volatile Sulfur Compounds |
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