Reaction of malonaldehyde with nucleic acid. I. Formation of fluorescent pyrimido(1,2-a)purin-10(3H)-one nucleosides.

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概要

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• The reactions of malonaldehyde with guanosine and 2′-deoxyguanosine proceed slowly under acidic conditions to give new pyrimidopurine nucleosides, <B>3a</B> and <B>3b</B>, respectively. These compounds emit strong yellow fluorescence and are hydrolyzed by NaOH into malonaldehyde and guanosine from <B>3a</B> (2′-deoxyguanosine from <B>3b</B>). From chemical and spectroscopic evidence, these compounds were deduced to be 3-β-D-ribofuranosylpyrimido[1,2-<I>a</I>]purin-10(3<I>H</I>)-one (<B>3a</B>) and 3-(2-deoxy-β-D-<I>erythro</I>-pentofuranosyl)pyrimido[1,2-<I>a</I>]purin-10(3<I>H</I>)-one (<B>3b</B>). No products were detected in the reaction mixture of malonaldehyde with 1-methylguanosine, adenosine, cytidine, uridine, thymidine, 2′-deoxyadenosine, or 2′-deoxycytidine.

• 公益社団法人 日本化学会の論文

著者

• Seto Hiroshi

  Tokyo Metropolitan Research Laboratory Of Public Health

• Okuda Taisuke

  College of Science and Technology, Nihon University

• Takesue Tomoyuki

  College of Science and Technology, Nihon University

• Ikemura Tadashi

  College of Science and Technology, Nihon University

関連論文

• Hydroxylation of Deoxyguanosine at the C-8 Position in the Thiosulfate-Hydrogen Peroxide Reaction System. Evidence of Hydroxyl Radical Generation in the System
• Reaction of Malonaldehyde with Adenosine. Formation of a Novel Adduct Containing a Dioxazatricycloundecene Residue in the Base-pairing Region
• Negative Chemical Ionization Mass Spectrometry of Nucleosides
• Reaction of malonaldehyde with nucleic acid. I. Formation of fluorescent pyrimido(1,2-a)purin-10(3H)-one nucleosides.
• Reaction of malonaldehyde with nucleic acid. II. Formation of fluorescent pyrimido(1,2-a)purin-10(3H)-one mononucleotide.

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