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On the relative acidity and basicity of the amino groups of the nucleic acid bases

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Abstract

Quantum chemical calculations are reported on the deprotonation and protonation of the amino groups of the nucleic acid bases adenine, guanine and cytosine, in an attempt to compare the relative reactivities of these groups. In the light of renewed interest in the amino groups as reactive sites for certain carcinogenic and carcinostatic agents, we discuss the possible significance of our results for the interpretation of these molecular interactions.

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References

  1. Jerina, D. M., Daly, J. M., in: Drug metabolism, Parke, D. V., Smith, R. L. Eds., p. 15. London: Taylor and Francis 1976

    Google Scholar 

  2. Jerina, D. M., Lehr, R. E., Yagi, H., Hernandez, O., Dansette, P. M., Wislocki, P. G., Wood, A. W., Chang, R. L., Levin, W., Conney, A. H., in: In vitro metabolic activation in mutagenesis testing, de Serres, F. J., Fonts, J. R., Bend, J. R., Philpot, R. M., Eds., p. 259. Amsterdam: Elsevier/North Holland Biomedical Press 1976

    Google Scholar 

  3. Jerina, D. M., Lehr, R. E., in: Microsomes and drug oxidations, Ullrich, V., Roots, I., Hildebrant, A. G., Estabrook, R. W., Conney, A. H., Eds., p. 709. Oxford: Pergamon Press 1977

    Google Scholar 

  4. Weinstein, I. G., Jeffrey, A. M., Jennette, K. W., Blobstein, S. H., Harvey, R. G., Harris, C., Autrup, H., Kasai, H., Nakanishi, K.: Science193, 592 (1976)

    Google Scholar 

  5. Jennette, K. W., Jeffrey, A. M., Blobstein, S. H., Beland, F. A., Harvey, R. G., Weinstein, I. B.: Biochem.16, 932 (1977)

    Google Scholar 

  6. Nakanishi, K., Kasai, H., Cho, H., Harvey, R. G., Jeffrey, A. M., Jennette, K. W., Weinstein, I. B.: J. Am. Chem. Soc.99, 258 (1977)

    Google Scholar 

  7. Yagi, H., Akagi, H., Thakker, D. R., Mah, H. D., Koreeda, M., Jerina, D. M.: J. Am. Chem. Soc.99, 2358 (1977)

    Google Scholar 

  8. Brookes, P., King, H. W. S., Osborne, M. R., in: Polycyclic hydrocarbons and cancer, Gelboin, H., Ts'o, P. O. P., Eds. New York: Academic Press, in press (1978)

    Google Scholar 

  9. Hulbert, P. B.: Nature256, 146 (1975)

    Google Scholar 

  10. Yang, S. K., McCount, D. W., Gelboin, H. V., Miller, J. R., Roller, P. P.: J. Am. Chem. Soc.99, 5124 (1977)

    Google Scholar 

  11. Lavery, R., Pullman, A., Pullman, B.: Intern. J. Quantum Chem. Quantum Biol. Symp. 5, in press

  12. Szent-Gyorgyi, A.: Proc. Natl. Acad. Sci. USA74, 2844 (1977)

    Google Scholar 

  13. Szent-Gyorgyi, A., in: Search and discovery, Kaminer, B., Ed., p. 329. New York: Academic Press 1977

    Google Scholar 

  14. Demoulin, D., Armbruster, A. M., Pullman, B.: Theoret. Chim. Acta (Berl.)50, 75 (1978)

    Google Scholar 

  15. Demoulin, D., Armbruster, A. M., Pullman, B.: Chem. Biol. Interaction, in press

  16. Newton, M. D., Pople, J. A.: Gaussian 70, Q.C.P.E. Indiana University 1973

  17. Klint, D., Hahn, D.: Acta Physica Sci. Hung.27, 493 (1969)

    Google Scholar 

  18. Spencer, M.: Acta Cryst.12, 59 (1959);12, 66 (1959)

    Google Scholar 

  19. Stewart, R., Harris, M. G.: Can. J. Chem.55, 3807 (1977)

    Google Scholar 

  20. Pullman, A., in: Mecanismes d'alteration et de réparation du DNA, relations avec la mutagénèse et la cancérogénèse chimique. Paris: Colloque Intern. du C.N.R.S.256, 104 (1976)

    Google Scholar 

  21. McGhee, J. D., von Hippel, P. H.: Biochem.14, 1281 (1975)

    Google Scholar 

  22. Pullman, A., Perahia, D., Zakrzewska, K.: in preparation

  23. Hopkinson, A. C., Lien, M. H., Csizmadia, I. G., Yoster, K.: Theoret. Chim. Acta (Berl.)47, 97 (1978)

    Google Scholar 

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Lavery, R., Pullman, A. & Pullman, B. On the relative acidity and basicity of the amino groups of the nucleic acid bases. Theoret. Chim. Acta 50, 67–73 (1978). https://doi.org/10.1007/BF00552495

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  • DOI: https://doi.org/10.1007/BF00552495

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