Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reaction of Malonaldehyde with Nucleic Acid. II. Formation of Fluorescent Pyrimido[1,2-a]purin-10(3H)-one Mononucleotide
Hiroshi SetoTomoyuki TakesueTadashi Ikemura
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1985 Volume 58 Issue 12 Pages 3431-3435


The reaction of malonaldehyde under acidic conditions (pH 4.5) with guanosine 5′-monophosphate resulted in the formation of fluorescent 3-(β-D-ribofuranosyl)pyrimido[1,2-a]purin-10(3H)-one 5′-phosphate (3a). This adduct was also isolated from malonaldehyde-reacted RNA. The amount of 3a in the modified RNA was estimated to be 0.4 per cent by weight. The fluorescence spectrum of 3a (Ex max. 360 nm, Em max. 500 nm) was similar to that of guanine- and guanosine-malonaldehyde adducts which have the same type base structure. On the other hand, another type of fluorophore (Ex max. 390 nm, Em max. 460 nm) was also formed in the reaction of malonaldehyde with a nucleic acid polymer. Thus, at least two different types of fluorophores are present in malonaldehyde-reacted nucleic acid.

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