将 2-萘酚基团遗传整合到蛋白质中以进行位点特异性偶氮偶联。

Genetic incorporation of a 2-naphthol group into proteins for site-specific azo coupling.

机构信息

Chemistry and Chemical Biology Group, School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.

出版信息

Bioconjug Chem. 2013 Oct 16;24(10):1645-9. doi: 10.1021/bc400168u. Epub 2013 Oct 2.

DOI:10.1021/bc400168u

PMID:24073629

Abstract

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 °C), high efficiency, and excellent selectivity.

摘要

色氨酸的 2-萘酚类似物，2-氨基-3-(6-羟基-2-萘基)丙酸（NpOH），已经通过定向进化的正交氨酰-tRNA 合成酶/tRNA 对被引入到大肠杆菌中的蛋白质中。这是通过选择地在响应琥珀终止密码子 UAG 时对目标氨基酸进行充电来实现的。此外，已经揭示了在 2-萘酚基团和重氮化苯胺衍生物之间的化学选择性偶联反应，所述苯胺衍生物带有供电子部分取代。偶联反应需要非常温和的条件（pH7），具有高反应速率（在 0°C 下不到 2 小时）、高效率和极好的选择性。