Organic and biomolecular chemistry p. 5602 - 5607 (2020)
Update date:2022-08-04
Topics:
Deng, Jiajie
Guo, Guiling
Wu, Xueting
Yu, Zhipeng
Zhao, Xiaohu
A photo-induced 1,3-dipolar cycloaddition between nitrile imine and highly ring-strained NN 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.
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