C–S Coupling of DNA-Conjugated Aryl Iodides for DNA-Encoded Chemical Library Synthesis
Thioethers have been widely found in biologically active compounds, including pharmaceuticals. In this report, a highly efficient approach to on-DNA construction of thioethers via Cu-promoted Ullmann cross-coupling between DNA-conjugated aryl iodides and thiols is developed. This methodology was dem...
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| Veröffentlicht in: | Bioconjugate chemistry 2021-04, Vol.32 (4), p.685-689 |
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| container_end_page | 689 |
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| container_issue | 4 |
| container_start_page | 685 |
| container_title | Bioconjugate chemistry |
| container_volume | 32 |
| creator | Ji, Yue Dai, Dongliang Luo, Huadong Shen, Simin Fan, Jing Wang, Zhao Chen, Min Wan, Jinqiao Li, Jin Ma, Huiyong Liu, Guansai |
| description | Thioethers have been widely found in biologically active compounds, including pharmaceuticals. In this report, a highly efficient approach to on-DNA construction of thioethers via Cu-promoted Ullmann cross-coupling between DNA-conjugated aryl iodides and thiols is developed. This methodology was demonstrated with medium to high yields, without obvious DNA damage. This reported reaction has strong potential for application in DNA-encoded chemical library synthesis. |
| doi_str_mv | 10.1021/acs.bioconjchem.1c00076 |
| format | Article |
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In this report, a highly efficient approach to on-DNA construction of thioethers via Cu-promoted Ullmann cross-coupling between DNA-conjugated aryl iodides and thiols is developed. This methodology was demonstrated with medium to high yields, without obvious DNA damage. This reported reaction has strong potential for application in DNA-encoded chemical library synthesis.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/acs.bioconjchem.1c00076</identifier><identifier>PMID: 33720689</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aromatic compounds ; Bioactive compounds ; Biological activity ; Chemical synthesis ; Cross coupling ; Deoxyribonucleic acid ; DNA ; DNA biosynthesis ; DNA damage ; Iodides ; Libraries ; Thioethers ; Thiols</subject><ispartof>Bioconjugate chemistry, 2021-04, Vol.32 (4), p.685-689</ispartof><rights>2021 American Chemical Society</rights><rights>Copyright American Chemical Society Apr 21, 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a385t-f8db4c5c2c9f52f085ebabeb0f1f92e9b16871264172294b216978beac5d5e23</citedby><cites>FETCH-LOGICAL-a385t-f8db4c5c2c9f52f085ebabeb0f1f92e9b16871264172294b216978beac5d5e23</cites><orcidid>0000-0001-8925-6093</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.bioconjchem.1c00076$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.bioconjchem.1c00076$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33720689$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ji, Yue</creatorcontrib><creatorcontrib>Dai, Dongliang</creatorcontrib><creatorcontrib>Luo, Huadong</creatorcontrib><creatorcontrib>Shen, Simin</creatorcontrib><creatorcontrib>Fan, Jing</creatorcontrib><creatorcontrib>Wang, Zhao</creatorcontrib><creatorcontrib>Chen, Min</creatorcontrib><creatorcontrib>Wan, Jinqiao</creatorcontrib><creatorcontrib>Li, Jin</creatorcontrib><creatorcontrib>Ma, Huiyong</creatorcontrib><creatorcontrib>Liu, Guansai</creatorcontrib><title>C–S Coupling of DNA-Conjugated Aryl Iodides for DNA-Encoded Chemical Library Synthesis</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>Thioethers have been widely found in biologically active compounds, including pharmaceuticals. In this report, a highly efficient approach to on-DNA construction of thioethers via Cu-promoted Ullmann cross-coupling between DNA-conjugated aryl iodides and thiols is developed. This methodology was demonstrated with medium to high yields, without obvious DNA damage. 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| ispartof | Bioconjugate chemistry, 2021-04, Vol.32 (4), p.685-689 |
| issn | 1043-1802 1520-4812 |
| language | eng |
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| source | ACS Publications |
| subjects | Aromatic compounds Bioactive compounds Biological activity Chemical synthesis Cross coupling Deoxyribonucleic acid DNA DNA biosynthesis DNA damage Iodides Libraries Thioethers Thiols |
| title | C–S Coupling of DNA-Conjugated Aryl Iodides for DNA-Encoded Chemical Library Synthesis |
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