A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria

Jiro Moriya; Takashi Yokogawa; Kawori Wakita; Takuya Ueda; Kazuya Nishikawa; Pamela F. Crain; Takeshi Hashizume; Steven C. Pomerantz; James A. McCloskey; Gota Kawai; Nobuhiro Hayashi; Shigeyuki Yokoyama; Kimitsuna Watanabe

doi:10.1021/bi00174a033

A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria

Jiro Moriya, Takashi Yokogawa, Kawori Wakita, Takuya Ueda, Kazuya Nishikawa, Pamela F. Crain, Takeshi Hashizume, Steven C. Pomerantz, James A. McCloskey, Gota Kawai, Nobuhiro Hayashi, Shigeyuki Yokoyama, Kimitsuna Watanabe^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

91 Citations (Scopus)

Abstract

Methionine tRNA was purified from bovine liver mitochondria, and its nucleotide sequence was determined. The tRNA possesses only three posttranscriptionally modified nucleosides, two pseudouridines in the anticodon and T stems and a previously unknown nucleoside specified by the gene sequence as cytidine, in the first position of the anticodon. Structure analysis of the anticodon nucleoside by mass spectrometry revealed a molecular mass 28 Da greater than that of cytidine, and unmodified ribose, with substitution at C-5 implied by hydrogen–deuterium exchange experiments. Proton NMR of the intact tRNA showed presence of a formyl moiety, thus leading to the candidate structure 5-formylcytidine (f⁵C), not a previously known compound. The structure assignment was confirmed by chemical synthesis and comparison of data from combined HPLC/mass spectrometry and proton NMR for the natural and synthetic nucleosides. The potential function of f⁵C in the tRNA^Met anticodon is discussed with regard to codon-anticodon interactions.

Original language	English
Pages (from-to)	2234-2239
Number of pages	6
Journal	Biochemistry
Volume	33
Issue number	8
DOIs	https://doi.org/10.1021/bi00174a033
Publication status	Published - 1994 Mar 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry

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Moriya, J., Yokogawa, T., Wakita, K., Ueda, T., Nishikawa, K., Crain, P. F., Hashizume, T., Pomerantz, S. C., McCloskey, J. A., Kawai, G., Hayashi, N., Yokoyama, S., & Watanabe, K. (1994). A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria. Biochemistry, 33(8), 2234-2239. https://doi.org/10.1021/bi00174a033

Moriya, J, Yokogawa, T, Wakita, K, Ueda, T, Nishikawa, K, Crain, PF, Hashizume, T, Pomerantz, SC, McCloskey, JA, Kawai, G, Hayashi, N, Yokoyama, S & Watanabe, K 1994, 'A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria', Biochemistry, vol. 33, no. 8, pp. 2234-2239. https://doi.org/10.1021/bi00174a033

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title = "A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria",

abstract = "Methionine tRNA was purified from bovine liver mitochondria, and its nucleotide sequence was determined. The tRNA possesses only three posttranscriptionally modified nucleosides, two pseudouridines in the anticodon and T stems and a previously unknown nucleoside specified by the gene sequence as cytidine, in the first position of the anticodon. Structure analysis of the anticodon nucleoside by mass spectrometry revealed a molecular mass 28 Da greater than that of cytidine, and unmodified ribose, with substitution at C-5 implied by hydrogen–deuterium exchange experiments. Proton NMR of the intact tRNA showed presence of a formyl moiety, thus leading to the candidate structure 5-formylcytidine (f5C), not a previously known compound. The structure assignment was confirmed by chemical synthesis and comparison of data from combined HPLC/mass spectrometry and proton NMR for the natural and synthetic nucleosides. The potential function of f5C in the tRNAMet anticodon is discussed with regard to codon-anticodon interactions.",

author = "Jiro Moriya and Takashi Yokogawa and Kawori Wakita and Takuya Ueda and Kazuya Nishikawa and Crain, {Pamela F.} and Takeshi Hashizume and Pomerantz, {Steven C.} and McCloskey, {James A.} and Gota Kawai and Nobuhiro Hayashi and Shigeyuki Yokoyama and Kimitsuna Watanabe",

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doi = "10.1021/bi00174a033",

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T1 - A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria

AU - Moriya, Jiro

AU - Yokogawa, Takashi

AU - Wakita, Kawori

AU - Ueda, Takuya

AU - Nishikawa, Kazuya

AU - Crain, Pamela F.

AU - Hashizume, Takeshi

AU - Pomerantz, Steven C.

AU - McCloskey, James A.

AU - Kawai, Gota

AU - Hayashi, Nobuhiro

AU - Yokoyama, Shigeyuki

AU - Watanabe, Kimitsuna

PY - 1994/3/1

Y1 - 1994/3/1

N2 - Methionine tRNA was purified from bovine liver mitochondria, and its nucleotide sequence was determined. The tRNA possesses only three posttranscriptionally modified nucleosides, two pseudouridines in the anticodon and T stems and a previously unknown nucleoside specified by the gene sequence as cytidine, in the first position of the anticodon. Structure analysis of the anticodon nucleoside by mass spectrometry revealed a molecular mass 28 Da greater than that of cytidine, and unmodified ribose, with substitution at C-5 implied by hydrogen–deuterium exchange experiments. Proton NMR of the intact tRNA showed presence of a formyl moiety, thus leading to the candidate structure 5-formylcytidine (f5C), not a previously known compound. The structure assignment was confirmed by chemical synthesis and comparison of data from combined HPLC/mass spectrometry and proton NMR for the natural and synthetic nucleosides. The potential function of f5C in the tRNAMet anticodon is discussed with regard to codon-anticodon interactions.

AB - Methionine tRNA was purified from bovine liver mitochondria, and its nucleotide sequence was determined. The tRNA possesses only three posttranscriptionally modified nucleosides, two pseudouridines in the anticodon and T stems and a previously unknown nucleoside specified by the gene sequence as cytidine, in the first position of the anticodon. Structure analysis of the anticodon nucleoside by mass spectrometry revealed a molecular mass 28 Da greater than that of cytidine, and unmodified ribose, with substitution at C-5 implied by hydrogen–deuterium exchange experiments. Proton NMR of the intact tRNA showed presence of a formyl moiety, thus leading to the candidate structure 5-formylcytidine (f5C), not a previously known compound. The structure assignment was confirmed by chemical synthesis and comparison of data from combined HPLC/mass spectrometry and proton NMR for the natural and synthetic nucleosides. The potential function of f5C in the tRNAMet anticodon is discussed with regard to codon-anticodon interactions.

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A Novel Modified Nucleoside Found at the First Position of the Anticodon of Methionine tRNA from Bovine Liver Mitochondria

Abstract

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