4.7 Article

Genetic Incorporation of a 2-Naphthol Group into Proteins for Site-Specific Azo Coupling

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BIOCONJUGATE CHEMISTRY
卷 24, 期 10, 页码 1645-1649

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AMER CHEMICAL SOC
DOI: 10.1021/bc400168u

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  1. University of California, Merced

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The 2-naphthol analogue of tyrosine, 2-amino-3-(6-hydroxy-2-naphthyl)propanoic acid (NpOH), has been genetically introduced into proteins in Escherichia coli. This is achieved through the directed evolution of orthogonal aminoacyl-tRNA synthetase/tRNA pairs that selectively charge the target amino acid in response to the amber stop codon, UAG. Moreover, chemoselective azo coupling reactions have been revealed between the 2-naphthol group and diazotized aniline derivatives that are substituted with an electron donating moiety. The coupling reactions required a very mild condition (pH 7) with great reaction rate (less than 2 h at 0 degrees C), high efficiency, and excellent selectivity.

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