Conclusions
-
1.
A method for synthesis of 5-S-cystamine-5,6-dihydrothymine was developed.
-
2.
This compound is stable in neutral and acid solutions but rapidly decomposes according to a first-order reaction at pH 10–12. It was found that decomposition is due to acidbase dissociation of 5-S-cystamine-5,6-dihydrothymine (pK ∼ 11.1) and that the rate of decomposition increases with an increase in the pH of the solutions.
-
3.
The products of cross-linking of these compounds, 5-S-cystamine-6-hydroxythymine and 5-S-cystamine-5,6-dihydrothymine, are formed in radiolysis of deaerated acid solutions containing thymine and cystamine.
Similar content being viewed by others
Literature cited
K. C. Smith, in: Photochemistry and Photobiology of Nucleic Acids, Vol. 1, S. Y. Wang (editor), Academic Press, New York-San Francisco-London (1976), p. 186.
M. D. Shetlar, Photochem. Photobiol. Rev.,5, 105 (1980).
K. C. Smith, Biochem. and Biophys. Res. Communs.,34, 354 (1969).
S. A. Grachev, E. V. Kropachev, and G. I. Litvyakova, Izv. Akad. Nauk SSSR, Ser, Khim., 1762 (1983).
G. Scholes, in: Effects of Ionizing Radiation on DNA. Physical, Chemical, and Biological Aspects, J. Hutterman, W. Kohlin, and R. Teoule (editors), Springer-Verlag, Berlin-Heidelberg-New York (1978), p. 153.
G. A. Bagiyan, S. A. Grachev, I. K. Koroleva, and N. V. Soroka, Zh. Obshch. Khim.,46, 365 (1976).
C. Nofre, A. Cier, R. Chapurlat, and J.-P. Mareschi, Bull. Soc. Chim. France, 332 (1965).
R. E. Cline and R. M. Fink, Anal. Chem.,28, 47 (1956).
N. K. Kochetkov, É. I. Budovskii, E. D. Sverdlov, N. A. Simukova, M. F. Turchinskii, and V. N. Shibaev, Organic Chemistry of Nucleic Acids [in Russian], Khimiya, Moscow (1970), p. 332.
R. E. Benesch and R. Benesch, J. Am. Chem. Soc.,77, 5877 (1955).
A. K. Pikaev and S. A. Kabakchi, Reactivity of the Primary Products of Radiolysis of Water. Handbook [in Russian], Energoizdat, Moscow (1982).
L. S. Myers and L. M. Theard, J. Am. Chem. Soc.,92, 2868 (1970).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1270–1275, June, 1984.
Rights and permissions
About this article
Cite this article
Grachev, S.A., Kropachev, E.V. & Litvyakova, G.I. Formation of 5-S-cystamine-5,6-dihydrothymine in radiolysis of aqueous solutions of thymine and cystamine. Russ Chem Bull 33, 1165–1170 (1984). https://doi.org/10.1007/BF00948980
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00948980