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Issue 12, 2016
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A genetically encoded multifunctional unnatural amino acid for versatile protein manipulations in living cells

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Abstract

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, Nε-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.

Graphical abstract: A genetically encoded multifunctional unnatural amino acid for versatile protein manipulations in living cells

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Publication details

The article was received on 15 Jun 2016, accepted on 01 Aug 2016 and first published on 01 Aug 2016


Article type: Edge Article
DOI: 10.1039/C6SC02615J
Citation: Chem. Sci., 2016,7, 7055-7060
  • Open access: Creative Commons BY license
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    A genetically encoded multifunctional unnatural amino acid for versatile protein manipulations in living cells

    Y. Ge, X. Fan and P. R. Chen, Chem. Sci., 2016, 7, 7055
    DOI: 10.1039/C6SC02615J

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