Genetic incorporation of a 2-naphthol group into proteins for site-specific azo coupling.
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.
Chemistry and Chemical Biology Group, School of Natural Sciences, University of California, Merced , 5200 North Lake Road, Merced, California 95343, United States.
Shuo
S
Chen
Meng-Lin
ML
Tsao
D000604:Amino Acyl-tRNA Synthetases / Q000235:genetics / Q000378:metabolism; D019020:Directed Molecular Evolution / Q000379:methods; D004926:Escherichia coli / Q000737:chemistry / Q000235:genetics* / Q000378:metabolism; D029968:Escherichia coli Proteins / Q000737:chemistry / Q000235:genetics* / Q000378:metabolism; D017017:Methanococcus / Q000201:enzymology / Q000235:genetics; D008958:Models, Molecular; D009284:Naphthols / Q000737:chemistry / Q000378:metabolism*; D015202:Protein Engineering / Q000379:methods; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000235:genetics* / Q000378:metabolism
D029968:Escherichia coli Proteins; D009284:Naphthols; D014443:Tyrosine; D000604:Amino Acyl-tRNA Synthetases; C028405:2-naphthol