Assembly drives regioselective azide-alkyne cycloaddition reaction
Abstract Azide-alkyne cycloaddition reaction is a very common organic reaction to synthesize nitrogen-containing heterocycles. Once catalyzed by Cu(I) or Ru(II), it turns out to be a click reaction and thus is widely applied in chemical biology for labeling. However, besides their poor regioselectiv...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-07-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-023-39658-0 |
| _version_ | 1797784489086156800 |
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| author | Qiaochu Jiang Wenjun Zhan Xiaoyang Liu Lin Bai Manli Wang Ying Xu Gaolin Liang |
| author_facet | Qiaochu Jiang Wenjun Zhan Xiaoyang Liu Lin Bai Manli Wang Ying Xu Gaolin Liang |
| author_sort | Qiaochu Jiang |
| collection | DOAJ |
| description | Abstract Azide-alkyne cycloaddition reaction is a very common organic reaction to synthesize nitrogen-containing heterocycles. Once catalyzed by Cu(I) or Ru(II), it turns out to be a click reaction and thus is widely applied in chemical biology for labeling. However, besides their poor regioselectivity towards this reaction, these metal ions are not biologically friendly. Hence, it is an urgent need to develop a metal-free azide–alkyne cycloaddition reaction for biomedical applications. In this work, we found that, in the absence of metal ions, supramolecular self-assembly in an aqueous solution could realize this reaction with excellent regioselectivity. Nap-Phe-Phe-Lys(azido)-OH firstly self-assembled into nanofibers. Then, Nap-Phe-Phe-Gly(alkynyl)-OH at equivalent concentration approached to react with the assembly to yield the cycloaddition product Nap-Phe-Phe-Lys(triazole)-Gly-Phe-Phe-Nap to form nanoribbons. Due to space confinement effect, the product was obtained with excellent regioselectivity. Employing the excellent properties of supramolecular self-assembly, we are applying this strategy to realize more reactions without metal ion catalysis. |
| first_indexed | 2024-03-13T00:41:37Z |
| format | Article |
| id | doaj.art-67d5ea6eb3604ba494520bdc9b2bf248 |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-03-13T00:41:37Z |
| publishDate | 2023-07-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-67d5ea6eb3604ba494520bdc9b2bf2482023-07-09T11:18:46ZengNature PortfolioNature Communications2041-17232023-07-011411710.1038/s41467-023-39658-0Assembly drives regioselective azide-alkyne cycloaddition reactionQiaochu Jiang0Wenjun Zhan1Xiaoyang Liu2Lin Bai3Manli Wang4Ying Xu5Gaolin Liang6State Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityState Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityState Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityState Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityState Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityState Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityState Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast UniversityAbstract Azide-alkyne cycloaddition reaction is a very common organic reaction to synthesize nitrogen-containing heterocycles. Once catalyzed by Cu(I) or Ru(II), it turns out to be a click reaction and thus is widely applied in chemical biology for labeling. However, besides their poor regioselectivity towards this reaction, these metal ions are not biologically friendly. Hence, it is an urgent need to develop a metal-free azide–alkyne cycloaddition reaction for biomedical applications. In this work, we found that, in the absence of metal ions, supramolecular self-assembly in an aqueous solution could realize this reaction with excellent regioselectivity. Nap-Phe-Phe-Lys(azido)-OH firstly self-assembled into nanofibers. Then, Nap-Phe-Phe-Gly(alkynyl)-OH at equivalent concentration approached to react with the assembly to yield the cycloaddition product Nap-Phe-Phe-Lys(triazole)-Gly-Phe-Phe-Nap to form nanoribbons. Due to space confinement effect, the product was obtained with excellent regioselectivity. Employing the excellent properties of supramolecular self-assembly, we are applying this strategy to realize more reactions without metal ion catalysis.https://doi.org/10.1038/s41467-023-39658-0 |
| spellingShingle | Qiaochu Jiang Wenjun Zhan Xiaoyang Liu Lin Bai Manli Wang Ying Xu Gaolin Liang Assembly drives regioselective azide-alkyne cycloaddition reaction Nature Communications |
| title | Assembly drives regioselective azide-alkyne cycloaddition reaction |
| title_full | Assembly drives regioselective azide-alkyne cycloaddition reaction |
| title_fullStr | Assembly drives regioselective azide-alkyne cycloaddition reaction |
| title_full_unstemmed | Assembly drives regioselective azide-alkyne cycloaddition reaction |
| title_short | Assembly drives regioselective azide-alkyne cycloaddition reaction |
| title_sort | assembly drives regioselective azide alkyne cycloaddition reaction |
| url | https://doi.org/10.1038/s41467-023-39658-0 |
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