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Quantum-chemical investigation of nitrosonium complexes of complementary pair 1-methylcytosine-9-methylguanine

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Abstract

By the method RI-MP2/L1 nitrosonium complexes were explored of 1-methylcytosine and 9-methylguanine, structural analogs of nucleotide bases cytosine and guanine, as well as of their complementary pair. The addition of a nitrosonium cation to the molecules of these compounds and to their pair leads to the formation of various types of nitrosonium complexes (1η–3η). n-Complexes with the coordination of NO+ cation to nitrogen and oxygen atoms are commonly more feasible in energy as compared with π-complexes. The complex with cation NO+ coordinated at the oxygen atom of the carbonyl group and N7 atom of the guanine fragment of the pair corresponds to the global minimum on the potential energy surface. The energy gain at the interaction of nitrosonium complexes of 1-methylcytosine and 9-methylguanine with 9-methylguanine and 1-methylcytosine respectively is usually larger than at the formation of a neutral pair 1-methylcytosine-9-methylguanine.

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References

  1. Hayat, S., Hasan, S.A., Mori, M., Fariduddin, Q., and Ahmad, A., Nitric Oxide in Plant Physiology, Hayat, S., Mori, M., Pichtel, J., and Ahmad, A., Eds., Weinheim: Wiley-VCH, 2010.

  2. Vanin, A.F., Ross. Khim. Zh., 2009, vol. 53, p.70.

    Google Scholar 

  3. Stojanović, S., Stanić, D., Nikolić, M., Spasić, M., and Niketić, V., Nitric Oxide, 2004, vol. 11, p. 256.

    Article  Google Scholar 

  4. Lipton, S.A., Choi, Y.-B., Pan, Z.-H., Lei, S.Z., Chen, H.-S.V., Sucher, N.J., Loscalzo, J., Singel, D.J., and Stamler, J.S., Nature, 1993, vol. 364, p. 626.

    Article  CAS  Google Scholar 

  5. Stamler, J.S., Singel, D.J., and Loscalzo, J., Science, 1992, vol. 258, p. 1898.

    Article  CAS  Google Scholar 

  6. Kirchner, J.J., Sigurdsson, S.Th., and Hopkins, P.B., J. Am. Chem. Soc., 1992, vol. 114, p. 4021.

    Article  CAS  Google Scholar 

  7. Elcock, A.H., Lyne, P.D., Mulholland, A.J., Nandra, A., and Richards, W.G., J. Am. Chem. Soc., 1995, vol. 117, p. 4706.

    Article  CAS  Google Scholar 

  8. Chin, W., Mons, M., Piuzzi, F., Tardivel, B., Dimicoli, I., Gorb, L., and Leszczynski, J., J. Phys. Chem. A, 2004, vol. 108, p. 8237.

    Article  CAS  Google Scholar 

  9. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2011, vol. 47, p. 1703.

    Article  CAS  Google Scholar 

  10. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 52.

    Article  CAS  Google Scholar 

  11. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 1216.

    Article  CAS  Google Scholar 

  12. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 1337.

    Article  CAS  Google Scholar 

  13. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2013, vol. 49, p. 432.

    Article  CAS  Google Scholar 

  14. Ten, G.N., Yakovleva, A.A., Nechaev, V.V., and Baranov, V.I., J. Struct. Chem., 2012, vol. 53, 835.

    Article  CAS  Google Scholar 

  15. Rosokha, S.V. and Kochi, J.K., J. Am. Chem. Soc., 2001, vol. 123, p. 8985.

    Article  CAS  Google Scholar 

  16. Zefirov, Yu.V., Kristallografiya, 1997, vol. 42, p. 936.

    CAS  Google Scholar 

  17. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2., 1987, p. S1.

    Google Scholar 

  18. Borodkin, G.I. and Shubin, V.G., Russ. Chem. Rev., 2001, vol. 70, p. 211.

    Article  CAS  Google Scholar 

  19. Wink, D.A., Kasprzak, K.S., Maragos, C.M., Elespuru, R.K., Misra, M., Dunams, T.M., Cebula, T.A., Koch, W.H., Andrews, A.W., Allen, J.S., and Keefer, L.K., Science, 1991, vol. 254, p. 1001.

    Article  CAS  Google Scholar 

  20. Caulfield, J.L., Wishnok, J.S., and Tannenbaum, S.R., J. Biolog. Chem., 1998, vol. 273, p. 12689.

    Article  CAS  Google Scholar 

  21. Williams, D.L.H., Nitrosation Reactions and the Chemistry of Nitric Oxide, Amsterdam: Wiley, 2004.

    Google Scholar 

  22. Nitric Oxide. Biology and Pathobiology, Ignarro, L.J., Ed., San Diego: Academic Press, 2000.

    Google Scholar 

  23. Sholl, D.S. and Steckel, J.A., Density Functional Theory. A Practical Introduction, Hoboken: Wiley, 2009.

    Book  Google Scholar 

  24. Marenich, A.V., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. B, 2009, vol. 113, p. 6378.

    Article  CAS  Google Scholar 

  25. Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151.

    Article  CAS  Google Scholar 

  26. Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., 2005, vol. 54, p. 820.

    Article  CAS  Google Scholar 

  27. Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomery, J.A. Jr., J. Comput. Chem., 1993, vol. 14, p. 1347.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    R. V. Andreev, G. I. Borodkin & V. G. Shubin

  2. Novosibirsk State University, Novosibirsk, Russia

    G. I. Borodkin

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  1. R. V. Andreev
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  2. G. I. Borodkin
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  3. V. G. Shubin
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Correspondence to G. I. Borodkin.

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Original Russian Text © R.V. Andreev, G.I. Borodkin, V.G. Shubin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 683–688.

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Andreev, R.V., Borodkin, G.I. & Shubin, V.G. Quantum-chemical investigation of nitrosonium complexes of complementary pair 1-methylcytosine-9-methylguanine. Russ J Org Chem 51, 664–669 (2015). https://doi.org/10.1134/S1070428015050140

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  • DOI: https://doi.org/10.1134/S1070428015050140

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