期刊
CHEMICAL SCIENCE
卷 7, 期 12, 页码 7055-7060出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc02615j
关键词
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资金
- National Key Research and Development Program [2016YFA0501500]
- National Natural Science Foundation of China [21225206, 21432002, 21521003]
- National Basic Research Program of China [2012CB917301]
The genetic code expansion strategy allowed incorporation of unnatural amino acids (UAAs) bearing diverse functional groups into proteins, providing a powerful toolkit for protein manipulation in living cells. We report a multifunctional UAA, N-epsilon-p-azidobenzyloxycarbonyl lysine (PABK), that possesses a panel of unique properties capable of fulfilling various protein manipulation purposes. In addition to being used as a bioorthogonal ligation handle, an infrared probe and a photo-affinity reagent, PABK was shown to be chemically decaged by trans-cyclooctenols via a strain-promoted 1,3-dipolar cycloaddition, which provides a new bioorthogonal cleavage strategy for intracellular protein activation. The biocompatibility and efficiency of this method were demonstrated by decaging of a PABK-caged firefly luciferase under living conditions. We further extended this method to chemically rescue a bacterial toxin OspF inside mammalian host cells.
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