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Nucleic Acids Research, 1975, Vol. 2, No. 12 2209-2222
© 1975

Articles

Photodissociable dimer reduction products of 2-thiopyrimidine derivatives

Monika Wrona*, J. Giziewicz and D. Shugar

Department of Biophysics, Institute of Experimental Physics, University of Warsaw 02-089 Warszawa, Poland

*Monika Wrona, Department of Biophysics, Institute of Experimental Physics, University of Warsaw, 93 Zwirki i Wigury, 02-089 Warszawa, Poland.

Received September 12, 1975. Both 4,6-dimethyl-2-thiopyrimidine and its 1-methjrl derivative undergo polarographic reduction in aqueous medium, via a 1e/1H+ reduction to a free radical which rapidly dimerizes to products isolated and identified as 4,4'-bis-(4,6-dimethyl-3,4-dihydropyrlimidin-2-thione) and the corresponding 1-methyl dimer. The dimers may be oxidized electrolytically to regenerate the parent monomers. Both dimers also undergo photo-dissociation to quantitatively regenerate the parent monomers, in high quantum yield, 0.23 and 0.35 M/Einstein. The correlation between electrochemical and photochemical reductions of 2-thiopyrimidines are discussed, as well as the significance of the dimer photodissociation reactions in relation to nucleic acid photochemistry.


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