Versatile Synthesis of Symmetric and Unsymmetric Imines via Photoelectrochemical Catalysis: Application to N-Terminal Modification of Phenylalanine
A strategy that combines electrochemical synthesis and photoredox catalysis was reported for the efficient synthesis of imines. This approach was demonstrated to be highly versatile in producing various types of imines, including symmetric and unsymmetric imines, by exploring the impact of different...
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| Veröffentlicht in: | Chemistry : a European journal 2023-10, Vol.29 (57), p.e202301379-e202301379 |
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| container_end_page | e202301379 |
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| container_issue | 57 |
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| container_title | Chemistry : a European journal |
| container_volume | 29 |
| creator | Chiang, Chien-Wei Li, Hung-Li Lin, Ting-Jun Chen, Hung-Chi Chou, Yi-Hsien Chou, Chih-Ju |
| description | A strategy that combines electrochemical synthesis and photoredox catalysis was reported for the efficient synthesis of imines. This approach was demonstrated to be highly versatile in producing various types of imines, including symmetric and unsymmetric imines, by exploring the impact of different substituents on the benzene ring of the arylamine. Additionally, the method was specifically applied to modify N-terminal phenylalanine residues and was found to be successful in photoelectrochemical bioconjugation between NH2-Phe-OMe and aryl methylamines, leading to the synthesis of phenylalanine-containing imines. Therefore, this technique would present a convenient and efficient platform for synthesizing imines, with promising applications in chemical biology, drug development, and organic synthesis. |
| doi_str_mv | 10.1002/chem.202301379 |
| format | Article |
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This approach was demonstrated to be highly versatile in producing various types of imines, including symmetric and unsymmetric imines, by exploring the impact of different substituents on the benzene ring of the arylamine. Additionally, the method was specifically applied to modify N-terminal phenylalanine residues and was found to be successful in photoelectrochemical bioconjugation between NH2-Phe-OMe and aryl methylamines, leading to the synthesis of phenylalanine-containing imines. Therefore, this technique would present a convenient and efficient platform for synthesizing imines, with promising applications in chemical biology, drug development, and organic synthesis.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202301379</identifier><identifier>PMID: 37434348</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Amines ; Benzene ; Catalysis ; Chemical reactions ; Chemical synthesis ; Chemistry ; Cross coupling ; Drug development ; Electrochemistry ; Imines ; Organic compounds ; Phenylalanine ; Photoredox catalysis</subject><ispartof>Chemistry : a European journal, 2023-10, Vol.29 (57), p.e202301379-e202301379</ispartof><rights>2023 Wiley-VCH GmbH.</rights><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c323t-2d054e7d1524df3550cb0bfd478aa93885272584d7902cb9e049fc2169359ba63</citedby><cites>FETCH-LOGICAL-c323t-2d054e7d1524df3550cb0bfd478aa93885272584d7902cb9e049fc2169359ba63</cites><orcidid>0000-0001-9399-8284</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37434348$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chiang, Chien-Wei</creatorcontrib><creatorcontrib>Li, Hung-Li</creatorcontrib><creatorcontrib>Lin, Ting-Jun</creatorcontrib><creatorcontrib>Chen, Hung-Chi</creatorcontrib><creatorcontrib>Chou, Yi-Hsien</creatorcontrib><creatorcontrib>Chou, Chih-Ju</creatorcontrib><title>Versatile Synthesis of Symmetric and Unsymmetric Imines via Photoelectrochemical Catalysis: Application to N-Terminal Modification of Phenylalanine</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A strategy that combines electrochemical synthesis and photoredox catalysis was reported for the efficient synthesis of imines. This approach was demonstrated to be highly versatile in producing various types of imines, including symmetric and unsymmetric imines, by exploring the impact of different substituents on the benzene ring of the arylamine. Additionally, the method was specifically applied to modify N-terminal phenylalanine residues and was found to be successful in photoelectrochemical bioconjugation between NH2-Phe-OMe and aryl methylamines, leading to the synthesis of phenylalanine-containing imines. Therefore, this technique would present a convenient and efficient platform for synthesizing imines, with promising applications in chemical biology, drug development, and organic synthesis.</description><subject>Amines</subject><subject>Benzene</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Cross coupling</subject><subject>Drug development</subject><subject>Electrochemistry</subject><subject>Imines</subject><subject>Organic compounds</subject><subject>Phenylalanine</subject><subject>Photoredox catalysis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkcFO3DAQhq2qqGyhV47IUi9csjieOI65oRW0SBSQgF4jx5lojZx4sb2V9jn6wnUE7KHywZrxN__M-CfkpGTLkjF-btY4LjnjwEqQ6hNZlIKXBchafCYLpipZ1ALUIfka4wtjTNUAX8ghyAryaRbk728MUSfrkD7uprTGaCP1Qw7GEVOwhuqpp89T3Mc3o50w0j9W04e1Tx4dmhT8PIg12tGVTtrtsswFvdxsXM4l6yeaPL0rnjDk6gz98r0dPp5yu4c1TjunnZ6y-DE5GLSL-O39PiLP11dPq5_F7f2Pm9XlbWGAQyp4z0SFss8bV_0AQjDTsW7oK9loraBpBJdcNFUvFeOmU8gqNRhe1gqE6nQNR-TsTXcT_OsWY2pHGw26PAX6bWx5AzVXQtYz-v0_9MVvQ95kpqTMvUuATC3fKBN8jAGHdhPsqMOuLVk729XOv9Tu7coFp--y227Efo9_-AP_ALYVkpI</recordid><startdate>20231013</startdate><enddate>20231013</enddate><creator>Chiang, Chien-Wei</creator><creator>Li, Hung-Li</creator><creator>Lin, Ting-Jun</creator><creator>Chen, Hung-Chi</creator><creator>Chou, Yi-Hsien</creator><creator>Chou, Chih-Ju</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9399-8284</orcidid></search><sort><creationdate>20231013</creationdate><title>Versatile Synthesis of Symmetric and Unsymmetric Imines via Photoelectrochemical Catalysis: Application to N-Terminal Modification of Phenylalanine</title><author>Chiang, Chien-Wei ; Li, Hung-Li ; Lin, Ting-Jun ; Chen, Hung-Chi ; Chou, Yi-Hsien ; Chou, Chih-Ju</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c323t-2d054e7d1524df3550cb0bfd478aa93885272584d7902cb9e049fc2169359ba63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Amines</topic><topic>Benzene</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Cross coupling</topic><topic>Drug development</topic><topic>Electrochemistry</topic><topic>Imines</topic><topic>Organic compounds</topic><topic>Phenylalanine</topic><topic>Photoredox catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chiang, Chien-Wei</creatorcontrib><creatorcontrib>Li, Hung-Li</creatorcontrib><creatorcontrib>Lin, Ting-Jun</creatorcontrib><creatorcontrib>Chen, Hung-Chi</creatorcontrib><creatorcontrib>Chou, Yi-Hsien</creatorcontrib><creatorcontrib>Chou, Chih-Ju</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chiang, Chien-Wei</au><au>Li, Hung-Li</au><au>Lin, Ting-Jun</au><au>Chen, Hung-Chi</au><au>Chou, Yi-Hsien</au><au>Chou, Chih-Ju</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Versatile Synthesis of Symmetric and Unsymmetric Imines via Photoelectrochemical Catalysis: Application to N-Terminal Modification of Phenylalanine</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2023-10-13</date><risdate>2023</risdate><volume>29</volume><issue>57</issue><spage>e202301379</spage><epage>e202301379</epage><pages>e202301379-e202301379</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A strategy that combines electrochemical synthesis and photoredox catalysis was reported for the efficient synthesis of imines. This approach was demonstrated to be highly versatile in producing various types of imines, including symmetric and unsymmetric imines, by exploring the impact of different substituents on the benzene ring of the arylamine. Additionally, the method was specifically applied to modify N-terminal phenylalanine residues and was found to be successful in photoelectrochemical bioconjugation between NH2-Phe-OMe and aryl methylamines, leading to the synthesis of phenylalanine-containing imines. Therefore, this technique would present a convenient and efficient platform for synthesizing imines, with promising applications in chemical biology, drug development, and organic synthesis.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>37434348</pmid><doi>10.1002/chem.202301379</doi><orcidid>https://orcid.org/0000-0001-9399-8284</orcidid></addata></record> |
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| source | Access via Wiley Online Library |
| subjects | Amines Benzene Catalysis Chemical reactions Chemical synthesis Chemistry Cross coupling Drug development Electrochemistry Imines Organic compounds Phenylalanine Photoredox catalysis |
| title | Versatile Synthesis of Symmetric and Unsymmetric Imines via Photoelectrochemical Catalysis: Application to N-Terminal Modification of Phenylalanine |
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