A novel lysine-substituted nucleoside in the first position of the anticodon of minor isoleucine tRNA from Escherichia coli

T. Muramatsu, S. Yokoyama, N. Horie, A. Matsuda, Takuya Ueda, Z. Yamaizumi, Y. Kuchino, S. Nishimura, T. Miyazawa

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Abstract

A minor species of isoleucine tRNA (tRNA(minor)(Ile)) specific to the codon AUA has been isolated from Escherichia coli B and a modified nucleoside N+ has been found in the first position of the anticodon (Harada, F., and Nishimura, S. (1974) Biochemistry 13, 300-307). In the present study, tRNA(minor)(Ile) was purified from E. coli A19, and nucleoside N+ was prepared, by high-performance liquid chromatography, in an amount (0.6 A260 units) sufficient for the determination of chemical structures. By 400 MHz 1H NMR analysis, nucleoside N+ was found to have a pyrimidine moiety and a lysine moiety, the ε-amino group of which was involved in the linkage between these two moieties. From the NMR analysis together with mass spectrometry, the structure of nucleoside N+ was determined as 4-amino-2-(N6-lysino)-1-(β-D-ribofuranoysl)pyrimidinium ('lysidine'), which was confirmed by chemical synthesis. Lysidine is a novel type of modified cytidine with a lysine moiety and has one positive charge. Probably because of such a unique structure, lysidine in the first position of anticodon recognizes adenosine but not guanosine in the third position of codon.

Original languageEnglish
Pages (from-to)9261-9267
Number of pages7
JournalJournal of Biological Chemistry
Volume263
Issue number19
Publication statusPublished - 1988 Jan 1
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Cell Biology

Cite this

Muramatsu, T., Yokoyama, S., Horie, N., Matsuda, A., Ueda, T., Yamaizumi, Z., Kuchino, Y., Nishimura, S., & Miyazawa, T. (1988). A novel lysine-substituted nucleoside in the first position of the anticodon of minor isoleucine tRNA from Escherichia coli. Journal of Biological Chemistry, 263(19), 9261-9267.