Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimidopurin-10(3H)-one Nucleosides

Article abstract of DOI:10.1246/bcsj.56.1799

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