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

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• 作者：R. V. Andreev ; G. I. Borodkin ; V. G. Shubin
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2015
• 出版时间：May 2015
• 年：2015
• 卷：51
• 期：5
• 页码：664-669
• 全文大小：680 KB
• 参考文献：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.
  3.Stojanovi膰, S., Stani膰, D., Nikoli膰, M., Spasi膰, M., and Niketi膰, V., Nitric Oxide, 2004, vol. 11, p. 256.View Article
  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.View Article
  5.Stamler, J.S., Singel, D.J., and Loscalzo, J., Science, 1992, vol. 258, p. 1898.View Article
  6.Kirchner, J.J., Sigurdsson, S.Th., and Hopkins, P.B., J. Am. Chem. Soc., 1992, vol. 114, p. 4021.View Article
  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.View Article
  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.View Article
  9.Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2011, vol. 47, p. 1703.View Article
  10.Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 52.View Article
  11.Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 1216.View Article
  12.Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 1337.View Article
  13.Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2013, vol. 49, p. 432.View Article
  14.Ten, G.N., Yakovleva, A.A., Nechaev, V.V., and Baranov, V.I., J. Struct. Chem., 2012, vol. 53, 835.View Article
  15.Rosokha, S.V. and Kochi, J.K., J. Am. Chem. Soc., 2001, vol. 123, p. 8985.View Article
  16.Zefirov, Yu.V., Kristallografiya, 1997, vol. 42, p. 936.
  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.
  18.Borodkin, G.I. and Shubin, V.G., Russ. Chem. Rev., 2001, vol. 70, p. 211.View Article
  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.View Article
  20.Caulfield, J.L., Wishnok, J.S., and Tannenbaum, S.R., J. Biolog. Chem., 1998, vol. 273, p. 12689.View Article
  21.Williams, D.L.H., Nitrosation Reactions and the Chemistry of Nitric Oxide, Amsterdam: Wiley, 2004.
  22. Nitric Oxide. Biology and Pathobiology, Ignarro, L.J., Ed., San Diego: Academic Press, 2000.
  23.Sholl, D.S. and Steckel, J.A., Density Functional Theory. A Practical Introduction, Hoboken: Wiley, 2009.View Article
  24.Marenich, A.V., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. B, 2009, vol. 113, p. 6378.View Article
  25.Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151.View Article
  26.Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., 2005, vol. 54, p. 820.View Article
  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.View Article
  
• 作者单位：R. V. Andreev (1)
  G. I. Borodkin (1) (2)
  V. G. Shubin (1)
  
  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent鈥檈va 9, Novosibirsk, 630090, Russia
  2. Novosibirsk State University, Novosibirsk, Russia
  
• 刊物主题：Organic Chemistry;
• 出版者：Springer US
• ISSN：1608-3393

文摘

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 (1畏鈥?畏). n-Complexes with the coordination of NO+ cation to nitrogen and oxygen atoms are commonly more feasible in energy as compared with 蟺-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.