A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid
A photochemoenzymatic halodecarboxylation of ferulic acid was achieved using vanadate‐dependent chloroperoxidase as (bio)catalyst and oxygen and organic solvent as sole stoichiometric reagents in a biphasic system. Performance and selectivity were improved through a phase transfer catalyst, reaching...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2022-10, Vol.23 (19), p.e202200367-n/a |
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| container_title | Chembiochem : a European journal of chemical biology |
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| creator | Zippilli, Claudio Bartolome, Miguel Jimenez Hilberath, Thomas Botta, Lorenzo Hollmann, Frank Saladino, Raffaele |
| description | A photochemoenzymatic halodecarboxylation of ferulic acid was achieved using vanadate‐dependent chloroperoxidase as (bio)catalyst and oxygen and organic solvent as sole stoichiometric reagents in a biphasic system. Performance and selectivity were improved through a phase transfer catalyst, reaching a turnover number of 660.000 for the enzyme.
Halodecarboxylation of α,β‐unsaturated ferulic acid was achieved by combining photo‐, bio‐ and phase transfer catalysis in a biphasic system. Reactive hypobromite was formed in situ by combining Blue‐LED and vanadium chloroperoxidase, and efficiently transferred from the aqueous to the organic layer by a phase‐transfer catalyst, improving overall performance and selectivity. |
| doi_str_mv | 10.1002/cbic.202200367 |
| format | Article |
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Halodecarboxylation of α,β‐unsaturated ferulic acid was achieved by combining photo‐, bio‐ and phase transfer catalysis in a biphasic system. Reactive hypobromite was formed in situ by combining Blue‐LED and vanadium chloroperoxidase, and efficiently transferred from the aqueous to the organic layer by a phase‐transfer catalyst, improving overall performance and selectivity.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.202200367</identifier><identifier>PMID: 35921215</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Catalysis ; Catalysts ; Chloride Peroxidase ; Coumaric Acids ; Ferulic acid ; halodecarboxylation ; Oxygen ; Phase transfer catalysts ; phase-transfer catalysis ; photobiocatalysis ; photochemoenzymatic reactions ; Reagents ; Selectivity ; Solvents ; Vanadate ; Vanadates ; vanadium chloroperoxidase</subject><ispartof>Chembiochem : a European journal of chemical biology, 2022-10, Vol.23 (19), p.e202200367-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-bc83e1329d16a682771af30d7b568eed37280f8b707904cdb3d34d2a30b153b3</citedby><cites>FETCH-LOGICAL-c4687-bc83e1329d16a682771af30d7b568eed37280f8b707904cdb3d34d2a30b153b3</cites><orcidid>0000-0003-4821-756X ; 0000-0002-9778-2509</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.202200367$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbic.202200367$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35921215$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zippilli, Claudio</creatorcontrib><creatorcontrib>Bartolome, Miguel Jimenez</creatorcontrib><creatorcontrib>Hilberath, Thomas</creatorcontrib><creatorcontrib>Botta, Lorenzo</creatorcontrib><creatorcontrib>Hollmann, Frank</creatorcontrib><creatorcontrib>Saladino, Raffaele</creatorcontrib><title>A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>Chembiochem</addtitle><description>A photochemoenzymatic halodecarboxylation of ferulic acid was achieved using vanadate‐dependent chloroperoxidase as (bio)catalyst and oxygen and organic solvent as sole stoichiometric reagents in a biphasic system. Performance and selectivity were improved through a phase transfer catalyst, reaching a turnover number of 660.000 for the enzyme.
Halodecarboxylation of α,β‐unsaturated ferulic acid was achieved by combining photo‐, bio‐ and phase transfer catalysis in a biphasic system. Reactive hypobromite was formed in situ by combining Blue‐LED and vanadium chloroperoxidase, and efficiently transferred from the aqueous to the organic layer by a phase‐transfer catalyst, improving overall performance and selectivity.</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chloride Peroxidase</subject><subject>Coumaric Acids</subject><subject>Ferulic acid</subject><subject>halodecarboxylation</subject><subject>Oxygen</subject><subject>Phase transfer catalysts</subject><subject>phase-transfer catalysis</subject><subject>photobiocatalysis</subject><subject>photochemoenzymatic reactions</subject><subject>Reagents</subject><subject>Selectivity</subject><subject>Solvents</subject><subject>Vanadate</subject><subject>Vanadates</subject><subject>vanadium chloroperoxidase</subject><issn>1439-4227</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>eNqFkc9u00AQh1cIREvhyrGyxKWXhN1Ze9e-VEojSipVooeI62r_jMkW25vuxi3mxCPwjDwJjhIC9NLTjDTffJrRj5C3jE4ZpfDeGm-nQAEo5UI-I8cs59VECs6f7_scQB6RVyndUkorwdlLcsSLChiw4ph8nmU3q7AJdoVtwO770OqNt9mi75LzaL9i_PXj50WIwflu7JbDGrOFboJDq6MJ34Zm5EOXhTq7xNg34-7MeveavKh1k_DNvp6Q5eWH5Xwxuf708Wo-u57YXJRyYmzJkXGoHBNalCAl0zWnTppClIiOSyhpXRpJZUVz6wx3PHegOTWs4IafkPOddt2bFp3FbhN1o9bRtzoOKmiv_p90fqW-hHtVlTQvJYyCs70ghrse00a1PllsGt1h6JMCUUkh84LzEX33CL0NfezG7xRIAAG0YFvhdEfZGFKKWB-OYVRtE1PbxNQhsXHh9N8XDvifiEag2gEPvsHhCZ2aX1zN_8p_A0uipSM</recordid><startdate>20221006</startdate><enddate>20221006</enddate><creator>Zippilli, Claudio</creator><creator>Bartolome, Miguel Jimenez</creator><creator>Hilberath, Thomas</creator><creator>Botta, Lorenzo</creator><creator>Hollmann, Frank</creator><creator>Saladino, Raffaele</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</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>7QL</scope><scope>7QO</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-4821-756X</orcidid><orcidid>https://orcid.org/0000-0002-9778-2509</orcidid></search><sort><creationdate>20221006</creationdate><title>A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid</title><author>Zippilli, Claudio ; Bartolome, Miguel Jimenez ; Hilberath, Thomas ; Botta, Lorenzo ; Hollmann, Frank ; Saladino, Raffaele</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4687-bc83e1329d16a682771af30d7b568eed37280f8b707904cdb3d34d2a30b153b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chloride Peroxidase</topic><topic>Coumaric Acids</topic><topic>Ferulic acid</topic><topic>halodecarboxylation</topic><topic>Oxygen</topic><topic>Phase transfer catalysts</topic><topic>phase-transfer catalysis</topic><topic>photobiocatalysis</topic><topic>photochemoenzymatic reactions</topic><topic>Reagents</topic><topic>Selectivity</topic><topic>Solvents</topic><topic>Vanadate</topic><topic>Vanadates</topic><topic>vanadium chloroperoxidase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zippilli, Claudio</creatorcontrib><creatorcontrib>Bartolome, Miguel Jimenez</creatorcontrib><creatorcontrib>Hilberath, Thomas</creatorcontrib><creatorcontrib>Botta, Lorenzo</creatorcontrib><creatorcontrib>Hollmann, Frank</creatorcontrib><creatorcontrib>Saladino, Raffaele</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>Wiley Free Content</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zippilli, Claudio</au><au>Bartolome, Miguel Jimenez</au><au>Hilberath, Thomas</au><au>Botta, Lorenzo</au><au>Hollmann, Frank</au><au>Saladino, Raffaele</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>Chembiochem</addtitle><date>2022-10-06</date><risdate>2022</risdate><volume>23</volume><issue>19</issue><spage>e202200367</spage><epage>n/a</epage><pages>e202200367-n/a</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>A photochemoenzymatic halodecarboxylation of ferulic acid was achieved using vanadate‐dependent chloroperoxidase as (bio)catalyst and oxygen and organic solvent as sole stoichiometric reagents in a biphasic system. Performance and selectivity were improved through a phase transfer catalyst, reaching a turnover number of 660.000 for the enzyme.
Halodecarboxylation of α,β‐unsaturated ferulic acid was achieved by combining photo‐, bio‐ and phase transfer catalysis in a biphasic system. Reactive hypobromite was formed in situ by combining Blue‐LED and vanadium chloroperoxidase, and efficiently transferred from the aqueous to the organic layer by a phase‐transfer catalyst, improving overall performance and selectivity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35921215</pmid><doi>10.1002/cbic.202200367</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-4821-756X</orcidid><orcidid>https://orcid.org/0000-0002-9778-2509</orcidid><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Catalysis Catalysts Chloride Peroxidase Coumaric Acids Ferulic acid halodecarboxylation Oxygen Phase transfer catalysts phase-transfer catalysis photobiocatalysis photochemoenzymatic reactions Reagents Selectivity Solvents Vanadate Vanadates vanadium chloroperoxidase |
| title | A Photochemoenzymatic Hunsdiecker‐Borodin‐Type Halodecarboxylation of Ferulic Acid |
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