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

Article abstract of DOI:10.1246/bcsj.58.3431

The reaction of malonaldehyde under acidic conditions (pH 4.5) with guanosine 5'-monophosphate resulted in the formation of fluorescent 3-(β-ribofuranosyl)pyrimido<1,2-a>purin-10(3H)-one 5'-phosphate (3a).The 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 (E_x max. 360 nm, E_m 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 (E_x max. 390 nm, E_m 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.