Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 29, Pages 5602-5607Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01027h
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Funding
- National Natural Science Foundation of China [21502130]
- 1000-Youth Talents Program
- Fundamental Research Funds for the Central Universities
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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.
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