Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives
Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functio...
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| Format: | Article |
| Language: | English |
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Wiley
2025-01-01
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| Series: | Advanced Science |
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| Online Access: | https://doi.org/10.1002/advs.202411579 |
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| author | Bo Dong Weiguan Qi Yifeng Chen Yufei Zhang Shiyu Gu Jianlin Zhao Qingfa Zhou Jian Shen Lan‐Gui Xie |
| author_facet | Bo Dong Weiguan Qi Yifeng Chen Yufei Zhang Shiyu Gu Jianlin Zhao Qingfa Zhou Jian Shen Lan‐Gui Xie |
| author_sort | Bo Dong |
| collection | DOAJ |
| description | Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, a visible light‐induced three‐component reaction involving arylthianthrenium salts, amino acid/peptide derivatives, and alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex bioactive molecules. This method offers a promising alternative route for modular synthesis of peptide‐derived bio‐relevant compounds |
| format | Article |
| id | doaj-art-ee46829cc9864fa7bc4b04e573eeb7bc |
| institution | Kabale University |
| issn | 2198-3844 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Advanced Science |
| spelling | doaj-art-ee46829cc9864fa7bc4b04e573eeb7bc2025-01-13T15:29:43ZengWileyAdvanced Science2198-38442025-01-01122n/an/a10.1002/advs.202411579Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide DerivativesBo Dong0Weiguan Qi1Yifeng Chen2Yufei Zhang3Shiyu Gu4Jianlin Zhao5Qingfa Zhou6Jian Shen7Lan‐Gui Xie8National and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaNational and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaNational and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaState Key Laboratory of Natural Medicines Department of Organic Chemistry China Pharmaceutical University Nanjing 210009 P. R. ChinaNational and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaNational and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaState Key Laboratory of Natural Medicines Department of Organic Chemistry China Pharmaceutical University Nanjing 210009 P. R. ChinaNational and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaNational and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science Nanjing Normal University Nanjing 210023 P. R. ChinaAbstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, a visible light‐induced three‐component reaction involving arylthianthrenium salts, amino acid/peptide derivatives, and alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex bioactive molecules. This method offers a promising alternative route for modular synthesis of peptide‐derived bio‐relevant compoundshttps://doi.org/10.1002/advs.202411579amino acidcaptodative effectlate‐stage functionalizationradical couplingthianthrenium salt |
| spellingShingle | Bo Dong Weiguan Qi Yifeng Chen Yufei Zhang Shiyu Gu Jianlin Zhao Qingfa Zhou Jian Shen Lan‐Gui Xie Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives Advanced Science amino acid captodative effect late‐stage functionalization radical coupling thianthrenium salt |
| title | Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives |
| title_full | Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives |
| title_fullStr | Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives |
| title_full_unstemmed | Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives |
| title_short | Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives |
| title_sort | stabilized carbon radical mediated assembly of arylthianthrenium salts alkenes and amino acid peptide derivatives |
| topic | amino acid captodative effect late‐stage functionalization radical coupling thianthrenium salt |
| url | https://doi.org/10.1002/advs.202411579 |
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