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Nucleic Acids Symposium Series 2005 49(1):265-266; doi:10.1093/nass/49.1.265
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© 2005 Oxford University Press

A simple approach to sense codon-templated synthesis of natural/unnatural hybrid peptides

Keiichiro Kanatani, Shinsuke Sando and Yasuhiro Aoyama

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan

In the presence of Phe-SA, the stable sulfamoyl analogue of phenylalanyl adenylate, the codon (UUU/UUC) for phenylalanine (Phe) can be reassigned to naphthylalanine (Nap) bound to tRNAPhe. The efficiency and selectivity of this Phe-to-Nap reassignment induced by the "orthogonal reacylation stalling" method was demonstrated at the single-codon level in the translation of mRNAs of dihydrofolate reductase (DHFR) and a 24-mer oligopeptide. In the prokaryotic translation system with essential preincubation, the endogenous precharged phenylalanyl-tRNAPhe undergoes deacylation and reacylation of the resulting tRNAPhe is inhibited by the action of Phe-SA to kill the phenylalanyl-tRNA synthetase activity. The significance of the present small-molecule-based approach to sense-codon templated natural-unnatural peptides is discussed.


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