Abstract
Both 4,6-dimethyl-2-thipyrimidine and its 1-methyl derivative undergo polarographic reduction in aqueous medium, via a 1e/1H+ reduction to a free radical which rapidly dimerizes to products isolates and identified as 4,4'-bis-(4,6-dimethyl-3,4-dihydropyrimidin-2-thione) and the corresponding 1-methyl dimer. The dimers may be oxidized electrolytically to regenerate the parent monomers. Both dimers also undergo photodissociation 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.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- CAVALIERI L. F., LOWY B. A. A polarographic study of pyrimidines. Arch Biochem Biophys. 1952 Jan;35(1):83–92. doi: 10.1016/s0003-9861(52)80052-9. [DOI] [PubMed] [Google Scholar]
- Czochralska B., Shugar D. Photochemically reversible pyrimidine dimer product of electrochemical reduction of pyrimidone-2. Biochim Biophys Acta. 1972 Sep 29;281(1):1–10. doi: 10.1016/0005-2787(72)90182-7. [DOI] [PubMed] [Google Scholar]
- Psoda A., Kazimierczuk Z., Shugar D. Structure and tautomerism of the neutral and monoanionic forms of 4-thiouracil derivatives. J Am Chem Soc. 1974 Oct 30;96(22):6832–6839. doi: 10.1021/ja00829a003. [DOI] [PubMed] [Google Scholar]