Are guanine tetrads stabilised by bifurcated hydrogen bonds? An AIM topological analysis of the electronic density

PhysChemComm

Volumn 5, Issue , 2002, Pages 94-98

  Louit, Guillaume ^a   Hocquet, Alexandre ^a   Ghomi, Mahmoud ^a   Meyer, Michael ^b   Sühnel, Jürgen ^c  

^a CNRS   (France)

^b Revotar Biopharmaceuticals AG   (Germany)

^c FRITZ LIPMANN INSTITUTE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GUANINE; HYDROGEN;

ARTICLE; ATOM; CHEMICAL ANALYSIS; DENSITY; ELECTRONICS; HYDROGEN BOND; MOLECULAR STABILITY; PHYSICAL CHEMISTRY;

EID: 0042392176     PISSN: 14602733     EISSN: None     Source Type: Journal    
DOI: 10.1039/b204736e     Document Type: Article

References (40)

1. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991.
2. W. Saenger, Principles of Nucleic Acid Structure, ed. C. R. Cantor, Springer-Verlag, New York, 1984.
3. W. Guschlbauer, J. F. Chantot and D. Thiele, J. Biomol. Struct. Dyn., 1990, 3, 491-511.
4. J. Sühnel, Biopolymers (NAS), 2002, 61, 32-51; M. Meyer and J. Sühnel, Base Polyad Motifs in Nucleic Acids, in Computational Chemistry: Reviews of Current Trends, ed. J. Leszczynski, World Scientific, River Edge, NJ, vol. 8, in press.
5. J. Sühnel, Biopolymers (NAS), 2002, 61, 32-51; M. Meyer and J. Sühnel, Base Polyad Motifs in Nucleic Acids, in Computational Chemistry: Reviews of Current Trends, ed. J. Leszczynski, World Scientific, River Edge, NJ, vol. 8, in press.
6. D. J. Patel, S. Bouaziz, A. Kettanim and Y. Wang, Structures of guanine-rich and cytosine-rich quadruplexes formed in vitro by telomeric, centromeric and triplet repeat disease DNA sequences, in Oxford Handbook of Nucleic Acid Structure, ed. S. Neidle, Oxford, 1999, pp. 389-453.
7. E. Mezzina, P. Mariani, R. Itri, S. Masiero, S. Pieraaccini, G. P. Spada, F. Spinozzi, J. T. Davis and G. Gottarelli, Chem. Eur. J., 2002, 7, 388-395.
8. J. Gu and J. Leszczynski, Chem. Pys. Lett., 1999, 311, 209-214.
9. J. Gu and J. Leszczynski, J. Phys. Chem. A, 2000, 104, 6308-6313.
10. M. Meyer, M. Brandl and J. Sühnel, J. Comput. Chem., 2001, 22, 109-124.
11. M. Meyer, M. Brandl and J. Sühnel, J. Phys. Chem. A, 2001, 105, 8223-8225.
12. J. Gu and J. Leszczynski, J. Phys. Chem. A, 2002, 106, 529-532.
13. R. F. W. Bader, Atoms In Molecules. A Quantum Theory, Clarendon, Oxford, 1990.
14. M. T. Carroll and R. F. W. Bader, Mol. Phys., 1988, 65, 695.
15. U. Koch and P. L. A. Popelier, J. Phys. Chem., 1995, 99, 9747.
16. P. L. A. Popelier, J. Phys. Chem. A, 1998, 102, 1873.
17. P. Hobza, J. Sponer, E. Cubero, M. Orozco and F. Luque, J. Phys. Chem. B, 2000, 104, 6286-6292; J. Munoz, J. Sponer, P. Hobza, M. Orozco and F. J. Luque, J. Phys. Chem. B, 2001, 105(25), 6051-6060.
18. P. Hobza, J. Sponer, E. Cubero, M. Orozco and F. Luque, J. Phys. Chem. B, 2000, 104, 6286-6292; J. Munoz, J. Sponer, P. Hobza, M. Orozco and F. J. Luque, J. Phys. Chem. B, 2001, 105(25), 6051-6060.
19. A. Hocquet, Phys. Chem. Chem. Phys., 2001, 3, 3192-3199; G. Louit, A. Hocquet and M. Ghomi, Phys. Chem. Chem. Phys., 2002, 4 (DOI: 10.1039/b201339h).
20. A. Hocquet, Phys. Chem. Chem. Phys., 2001, 3, 3192-3199; G. Louit, A. Hocquet and M. Ghomi, Phys. Chem. Chem. Phys., 2002, 4 (DOI: 10.1039/b201339h).
21. J. Sponer, J. Leszczynski and P. Hobza, J. Phys. Chem., 1996, 100, 1965-1974.
22. A. D. Becke, J. Chem. Phys. A, 1993, 98, 5648; B. Miehlich, A. Savin, H. Stoll and H. Preuss, Chem. Phys. Lett., 1989, 157, 200; C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785; S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 1980, 58, 1200.
23. A. D. Becke, J. Chem. Phys. A, 1993, 98, 5648; B. Miehlich, A. Savin, H. Stoll and H. Preuss, Chem. Phys. Lett., 1989, 157, 200; C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785; S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 1980, 58, 1200.
24. A. D. Becke, J. Chem. Phys. A, 1993, 98, 5648; B. Miehlich, A. Savin, H. Stoll and H. Preuss, Chem. Phys. Lett., 1989, 157, 200; C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785; S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 1980, 58, 1200.
25. A. D. Becke, J. Chem. Phys. A, 1993, 98, 5648; B. Miehlich, A. Savin, H. Stoll and H. Preuss, Chem. Phys. Lett., 1989, 157, 200; C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785; S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 1980, 58, 1200.
26. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
27. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
28. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
29. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
30. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
31. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
32. R. Krishnan, Y. Binkley, R. Seeger and J. Pople, J. Chem. Phys., 1980, 72, 650-654; R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724; W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257; P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209; M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213; M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265.
33. N. Godbout, D. R. Salahub, J. Andzelm and E. Wimmer, Can. J. Chem., 1992, 70, 560-571.
34. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.
35. F. Biegler-König, J. Schönbohm and D. Bayles, J. Comput. Chem., 2001, 22, 545-559.
36. F. M. Aicken and P. L. A. Popelier, Can. J. Chem., 2000, 78, 415.
37. I. Rozas, I. Alkorta and J. Elguero, J. Phys. Chem. A, 1998, 102, 9925-9932.
38. N. Kobko, L. Paraskevas, E. del Rio and J. J. Dannenberg, J. Am. Chem. Soc., 2001, 123, 4348-4349.
39. S. J. Grabowski, J. Mol. Struct., 2001, 562, 137-143.
40. G. Louit and A. Hocquet, to be published.