Issue 29, 2020
From the journal:

Organic & Biomolecular Chemistry

Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells†

Jiajie Deng,a   Xueting Wu,a   Guiling Guo,a   Xiaohu Zhaoa  and  Zhipeng Yu ORCID logo *a  

* Corresponding authors

a Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China
E-mail: zhipengy@scu.edu.cn

Abstract

A photo-induced 1,3-dipolar cycloaddition between nitrile imine and highly ring-strained N[double bond, length as m-dash]N double bond as a dipolarophile was discovered. The photo-isomerization of carbon-bridged octocyclic azobenzene (CBOA) into its trans-configuration accelerates the ligation reaction at a very rapid rate (28 400 M−1 s−1). The CBOA-based photo-click reaction was proved to be bioorthogonal. In addition, the NoxaB peptide was successfully cross-linked by a CBOA stapler which plays a dual role: photo-control of the conformation of the peptide and photo-conjugation of probes in live cells.

Graphical abstract: Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells

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Article information

DOI
https://doi.org/10.1039/D0OB01027H
Article type
Paper
Submitted
18 May 2020
Accepted
29 Jun 2020
First published
03 Jul 2020

Org. Biomol. Chem., 2020,18, 5602-5607

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Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells

J. Deng, X. Wu, G. Guo, X. Zhao and Z. Yu, Org. Biomol. Chem., 2020, 18, 5602 DOI: 10.1039/D0OB01027H

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