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

被引：22

作者：

Deng, Jiajie ^{[1
]}

Wu, Xueting ^{[1
]}

Guo, Guiling ^{[1
]}

Zhao, Xiaohu ^{[1
]}

Yu, Zhipeng ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, 29 Wangjiang Rd, Chengdu 610064, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 29期

基金：

中国国家自然科学基金;

关键词：

TRANS-CYCLOOCTENE; CLICK CHEMISTRY; DESIGN; PROTEIN; ALKENE;

D O I：

10.1039/d0ob01027h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photo-induced 1,3-dipolar cycloaddition between nitrile imine and highly ring-strained N = N double bond as a dipolarophile was discovered. The photo-isomerization of carbon-bridged octocyclic azobenzene (CBOA) into itstrans-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.

引用

页码：5602 / 5607

页数：6