Halogen bonding in DNA base pairs

Journal of the American Chemical Society

Volumn 134, Issue 11, 2012, Pages 5165-5172

  Parker, Anna J ^a   Stewart, John ^a   Donald, Kelling J ^a   Parish, Carol A ^a  

^a UNIVERSITY OF RICHMOND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTIFICIAL PROTEINS; BASE PAIRS; COPLANAR STRUCTURE; DNA BASE PAIRS; HALOGEN BONDING; HALOGEN BONDS; MODIFIED GUANINE; POLARIZABILITIES; RATIONAL DESIGN; STABLE STRUCTURES;

BROMINE; CHLORINE; HALOGENATION; HYDROGEN BONDS;

IODINE;

DNA BASE; GUANINE; HALOGEN; HYDROGEN;

ARTICLE; BASE PAIRING; CHEMICAL BINDING; CHEMICAL STRUCTURE; HALOGENATION; HYDROGEN BOND; POLARIZATION;

BASE PAIRING; BINDING SITES; DNA; HALOGENS; HYDROGEN BONDING; QUANTUM THEORY;

EID: 84858654839     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2105027     Document Type: Article

References (54)

1. Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; W. H. Freeman: San Francisco, 1960; see especially Chapters 1, 8-11.
2. Pauling, L. The Nature of the Chemical Bond, 3 rd ed.; Cornell University Press: Ithaca, NY, 1960. In this book, Pauling credits T. S. Moore and T. F. Winmill with the first mention of the hydrogen bond.
3. Huggins, M. L. J. Chem. Educ. 1960, 37, A754
4. Dumas, J.-M.; Peurichard, H.; Gomel, M. J. Chem. Res. Synop. 1978, 2, 54
5. For a historical overview of these interactions and examples of complexes stabilized by these interactions see Odd Hassel's Nobel Lecture (1969): http://www.nobelprize.org/nobel-prizes/chemistry/laureates/1969/hassel-lecture. html, republished in ref 6.
6. Hassel, O. Science 1970, 170, 497
7. Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686
8. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386
9. Politzer, P.; Murray, J. S.; Lane, P. Int. J. Quantum Chem. 2007, 107, 3046
10. Voth, A. R.; Khuu, P.; Oishi, K.; Ho, P. S. Nature Chem. 2009, 1, 74
11. Fourmigue, M. Curr. Opin. Solid State Mater. Sci. 2009, 13, 36
12. Espallargas, G. M.; Zordan, F.; Marin, L. A.; Adams, H.; Shankland, K.; van de Streek, J.; Brammer, L. Chem.-Eur. J. 2009, 15, 7554
13. Lu, Y.; Shi, T.; Wang, Y.; Yang, H.; Luo, X.; Jiang, H.; Zhu, W. J. Med. Chem. 2009, 52, 2854
14. Bent, H. A. Chem. Rev. 1968, 68, 587
15. Murray, J. S.; Riley, K. E.; Politzer, P.; Clark, T. Aust. J. Chem. 2010, 63, 1598
16. Metrangolo, P.; Resnati, G. Science 2008, 321, 918
17. Shields, Z. P.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 2010, 110, 2823
18. Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 1992, 19, 57
19. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305
20. Politzer, P.; Murray, J. S. An Overview of Sigma-Hole Bonding: An Important and Widely Occuring Noncovalent Interaction. In Practical Aspects of Computational Chemistry Methods, Concepts and Applications; Leszczynski, J.; Shukla, M. K., Eds.; Springer: Heidelberg, 2009; Chapter 6.
21. Valerio, G.; Raos, G.; Meille, S. V.; Metrangolo, P.; Resnati, G. J. Phys. Chem. A 2000, 104, 1617
22. Li, Q.; Xu, X.; Liu, T.; Jing, B.; Li, W.; Cheng, J.; Gong, B.; Sun, J. Phys. Chem. Chem. Phys. 2010, 12, 6837
23. Donald, K. J.; Wittmaack, B. K.; Crigger, C. J. Phys. Chem. A 2010, 114, 7213
24. Li, Q.-Z.; Li, R.; Guo, P.; Li, H.; Li, W.-Z.; Cheng, J.-B. Comput. Theor. Chem. 2012, 980, 56
25. Li, Q.-Z.; Jing, B.; Li, R.; Liu, Z.-B.; Li, W.-Z.; Luan, F.; Cheng, J.-B.; Gong, B.-A.; Sun, J.-Z. Phys. Chem. Chem. Phys. 2011, 13, 2266
26. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789
27. Bayse, C. A.; Rafferty, E. R. Inorg. Chem. 2010, 49, 5365
28. Cody, V.; Murray-Rust, P. J. Mol. Struct. 1984, 112, 189
29. He, J.; Becher, G.; Budow, S.; Seela, F. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 573
30. Seela, F.; Shaikh, K.; Wiglenda, T. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 1239
31. Seela, F.; Kroschel, R. Nucleic Acids Res. 2003, 31, 7150
32. Seela, F.; Peng, X.; Li, H. J. Am. Chem. Soc. 2005, 127, 7739
33. Tawarada, R.; Seio, K.; Sekine, M. J. Org. Chem. 2008, 73, 383
34. Hawkins, C. L.; Davies, M. J. Chem. Res. Toxicol. 2002, 15, 83
35. Hawkins, C. L.; Davies, M. J. Chem. Res. Toxicol. 2001, 14, 1071
36. Gould, J. P.; Richards, J. T.; Miles, M. G. Water Res. 1984, 18, 991
37. Ohkubo, A.; Noma, Y.; Aoki, K.; Tsunoda, H.; Seio, K.; Sekine, M. J. Org. Chem. 2009, 74, 2817
38. Kawai, Y.; Matsui, Y.; Kondo, H.; Morinaga, H.; Uchida, K.; Miyoshi, N.; Nakamura, Y.; Osawa, T. Chem. Res. Toxicol. 2008, 21, 1407
39. Kawai, Y.; Morinaga, H.; Kondo, H.; Miyoshi, N.; Nakamura, Y.; Uchida, K.; Osawa, T. J. Biol. Chem. 2004, 279, 51241
40. Ikehara, M.; Ogiso, Y.; Maruyama, T. Chem. Pharm. Bull. 1977, 25, 575
41. Politzer, P.; Murray, J. S.; Concha, M. C. J. Mol. Model. 2007, 13, 643
42. Wang, Y.-H.; Lu, Y.-X.; Zou, J.-W.; Yu, Q.-S. Int. J. Quantum Chem. 2008, 108, 1083
43. Metrangolo, P.; Murray, J. S.; Pilati, T.; Politzer, P.; Resnati, G.; Terraneo, G. Cryst. Growth Des. 2011, 11, 4238
44. Frisch, M. J.; Gaussian 03, Revision B.04; Gaussian, Inc.: Wallingford, CT, 2004.
45. Becke, A. D. J. Phys. Chem. 1993, 98, 5648
46. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
47. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623
48. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. J. Comput. Chem. 2001, 22, 976
49. Petersen, K. A.; Shelper, B. C.; Figgen, D.; Stoll, H. J. Phys. Chem. A 2006, 110, 13877
50. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364
51. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
52. van der Wijst, T.; Guerra, C. F.; Swart, M.; Bickelhaupt, F. M. Chem. Phys. Lett. 2006, 426, 415
53. Hamm, M. L.; Parker, A. J.; Carman, J. L.; Steele, T. W. E.; Parish, C. A. J. Org. Chem. 2010, 75, 5661
54. Alabugin, I. B.; Manoharan, M.; Buck, M.; Clark, R. J. J. Mol. Struct. (THEOCHEM) 2007, 813, 21