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

被引：23

作者：

Chen, Shuo ^{[1
]}

Tsao, Meng-Lin ^{[1
]}

机构：

[1] Univ Calif Merced, Sch Nat Sci, Chem & Chem Biol Grp, Merced, CA 95343 USA

来源：

BIOCONJUGATE CHEMISTRY | 2013年 / 24卷 / 10期

关键词：

AZIDE-ALKYNE CYCLOADDITION; UNNATURAL AMINO-ACIDS; CHEMOSELECTIVE MODIFICATION; TYROSINE BIOCONJUGATION; SELECTIVE MODIFICATION; RECOMBINANT PROTEINS; SURFACE MODIFICATION; ESCHERICHIA-COLI; CLICK CHEMISTRY; CODE;

D O I：

10.1021/bc400168u

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：1645 / 1649

页数：5

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