Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis
[Display omitted] The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis reaction is for i...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2020-05, Vol.28 (9), p.115441-115441, Article 115441 |
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| container_end_page | 115441 |
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| container_issue | 9 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Potowski, Marco Esken, Robin Brunschweiger, Andreas |
| description | [Display omitted]
The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines. |
| doi_str_mv | 10.1016/j.bmc.2020.115441 |
| format | Article |
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The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2020.115441</identifier><identifier>PMID: 32222338</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>DNA-encoded library ; Encoded chemistry ; Multicomponent reaction ; Petasis reaction ; α-aryl glycines</subject><ispartof>Bioorganic & medicinal chemistry, 2020-05, Vol.28 (9), p.115441-115441, Article 115441</ispartof><rights>2020 Elsevier Ltd</rights><rights>Copyright © 2020 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-45684bdec525406bb1db97c8c457d0e2492c2b7bd76a762ef45a346522adbea23</citedby><cites>FETCH-LOGICAL-c353t-45684bdec525406bb1db97c8c457d0e2492c2b7bd76a762ef45a346522adbea23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089620302510$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32222338$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Potowski, Marco</creatorcontrib><creatorcontrib>Esken, Robin</creatorcontrib><creatorcontrib>Brunschweiger, Andreas</creatorcontrib><title>Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.</description><subject>DNA-encoded library</subject><subject>Encoded chemistry</subject><subject>Multicomponent reaction</subject><subject>Petasis reaction</subject><subject>α-aryl glycines</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEtP5DAQhK0VaBnY_QFckI9cMvidRJwQsCzSCDjA2fKjIzxK4mBnQPPvMTvAcftitVRV7foQOqZkSQlVZ-ulHdySEVZ2KoWgP9CCCiUqzlu6hxakVU1FmlYdoMOc14QQJlr6Ex1wVobzZoHeHpMZc2_mEEccOzw_A3ZxmiCd2TBtU_BhhGpKcYgzePwAs8kh4wTG_bPMEefYB4-nZ5OhcnEz9UV3dXeBu5gwjC76svfBJpO2OG_HcqEk_EL7nekz_P58j9DTn-vHy7_V6v7m9vJiVTku-VwJqRphPTjJpCDKWuptW7vGCVl7AqUOc8zW1tfK1IpBJ6ThQknGjLdgGD9Cp7vcUuFlA3nWQ8gO-t6MEDdZM94I0cq6VUVKd1KXYs4JOj2lMJRfa0r0B2-91oW3_uCtd7yL5-QzfmMH8N-OL8BFcL4TQCn5GiDp7EKhAj4kcLP2Mfwn_h0JqpIo</recordid><startdate>20200501</startdate><enddate>20200501</enddate><creator>Potowski, Marco</creator><creator>Esken, Robin</creator><creator>Brunschweiger, Andreas</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20200501</creationdate><title>Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis</title><author>Potowski, Marco ; Esken, Robin ; Brunschweiger, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-45684bdec525406bb1db97c8c457d0e2492c2b7bd76a762ef45a346522adbea23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>DNA-encoded library</topic><topic>Encoded chemistry</topic><topic>Multicomponent reaction</topic><topic>Petasis reaction</topic><topic>α-aryl glycines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Potowski, Marco</creatorcontrib><creatorcontrib>Esken, Robin</creatorcontrib><creatorcontrib>Brunschweiger, Andreas</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Potowski, Marco</au><au>Esken, Robin</au><au>Brunschweiger, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2020-05-01</date><risdate>2020</risdate><volume>28</volume><issue>9</issue><spage>115441</spage><epage>115441</epage><pages>115441-115441</pages><artnum>115441</artnum><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>32222338</pmid><doi>10.1016/j.bmc.2020.115441</doi><tpages>1</tpages></addata></record> |
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| source | Elsevier ScienceDirect Journals |
| subjects | DNA-encoded library Encoded chemistry Multicomponent reaction Petasis reaction α-aryl glycines |
| title | Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis |
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