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.
Die Reaktion von Malonaldehyd (I) mit Guanosin (IIa) bzw. T‐Desoxyguanosin (IIb) unter sauren Bedingungen führt zur Bildung der stark gelb fluoreszierenden Titel‐Nucleoside (III).
A new modified nucleoside was formed by the reaction of guanosine with malonaldehyde under acidic condition. This compound emitted strong yellow fluorescence and was hydrolyzed by NaOH into guanosine and malonaldehyde. Its structure was determined to be 1,N2-(1-propenyl-3-ylidene)guanosine by the spectroscopic analysis.
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