Assembly drives regioselective azide-alkyne cycloaddition reaction

Qiaochu Jiang, Wenjun Zhan, Xiaoyang Liu, Lin Bai, Manli Wang, Ying Xu and Gaolin Liang ()
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Qiaochu Jiang: Southeast University
Wenjun Zhan: Southeast University
Xiaoyang Liu: Southeast University
Lin Bai: Southeast University
Manli Wang: Southeast University
Ying Xu: Southeast University
Gaolin Liang: Southeast University

Nature Communications, 2023, vol. 14, issue 1, 1-7

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-023-39658-0

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