Analysis of the NMR spin-spin coupling mechanism across a H-bond: Nature of the H-bond in proteins

Journal of Physical Chemistry B

Volumn 108, Issue 3, 2004, Pages 1115-1129

  Tuttle, Tell ^a   Gräfenstein, Jürgen ^a   Wu, Anan ^a   Kraka, Elfi ^a   Cremer, Dieter ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; ELECTRIC FIELD EFFECTS; ELECTRON ENERGY LEVELS; ELECTRONIC STRUCTURE; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIZATION; PROTEINS;

CHARGE TRANSFER INTERACTION; SPIN-SPIN COUPLING CONSTANT; TWO-ORBITAL STERIC EXCHANGE INTERACTION; ZEROTH-ORDER DENSITY;

HYDROGEN BONDS;

EID: 0742321701     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0363951     Document Type: Article

References (84)

1. (a) Hydrogen Bonding in Biological Structures; Jeffrey, G. A., Saenger, W., Eds.; Springer: Berlin, 1991.
2. (b) Jeffrey, G. A. An Introduction to Hydrogen Bond; Oxford University Press: New York, 1997.
3. Scheiner, S. Hydrogen Bonding; Oxford University Press: New York, 1997.
4. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond; Oxford University Press: New York, 1999.
5. (a) Chang, H.-C.; Lee, K. M.; Jaing, J.-C.; Lin, M.-S.; Lin, I. J. B.; Lin, S. H. J. Chem. Phys. A 2002, 117, 1723.
6. (b) Lindeman, S. V.; Kosynkin, D.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 13268.
7. (c) Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101.
8. (d) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
9. (e) Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Parris, K.; Williams, K.; Rebek, J. J. Am. Chem. Soc. 1989, 111, 1082.
10. (f) Zimmerman, S. C.; VanZyl, C. M.; Hamilton, G. S. J. Am. Chem. Soc. 1989, 111, 1373.
11. (g) Shepodd, T. J.; Petti, M. A.; Dougherty, D. J. Am. Chem. Soc. 1988, 110, 1983.
12. (h) Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 245.
13. (i) Diedrich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362.
14. (a) Kim, K. S.; Tarakeshwar, P.; Lee, J. Y. Chem. Rev. 2000, 100, 4145.
15. (b) Brutschy, B. Chem. Rev. 2000, 100, 3891.
16. (a) Krimm, S.; Kuroiwa, K. Biopolymers 1968, 6, 401.
17. (b) Krimm, S. Nature 1966, 212, 1482.
18. (c) Scheiner, S.; Kar, T.; Gu, Y. J. Biol. Chem. 2001, 276, 9832.
19. (d) Burely, S. K.; Petsko, G. A. Science 1985, 229, 23.
20. (e) Blundell, T.; Singh, J.; Thornton, J.; Burley, S. K.; Petsko, G. A. Science 1986, 234, 1005.
21. (f) Burely, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986, 108, 7995.
22. (g) Brandl, M.; Weiss, M. S.; Jabs, A.; Suhnel J.; Hilgenfeld, R. J. Mol. Biol. 2001, 307, 357.
23. (h) Toth, G.; Murphy, R. F.; Lovas, S. Protein Eng. 2001, 14, 543.
24. Blatchford, M. A.; Raveendran, P.; Wallen, S. L. J. Am. Chem. Soc. 2002, 124, 14818.
25. Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441.
26. Dingley, A. J.; Grezeseik, S. J. Am. Chem. Soc. 1998, 120, 8293.
27. Pervushin, K.; Ono, A.; Fernández, C.; Szyperski, T.; Kainosho, M.; Wüthrich, K. Proc. Natl. Acad. Sci. U.S.A. 1999, 121, 6019.
28. Cordier, F.; Grezeseik, S. J. Am. Chem. Soc. 1999, 121, 1601.
29. Cornilescu, G.; Hu, J.-S.; Bax, A. J. Am. Chem. Soc. 1999, 121, 2949.
30. Cornilescu, G.; Ramirez, B. E.; Frank, M. K.; Clore, G. M.; Gronenborn, A. M.; Bax, A. J. Am. Chem. Soc. 1999, 121, 6275.
31. Cordier, F.; Rogowski, M. Grzesiek, S.; Bax, A. J. Magn. Reson. 1999, 140, 510.
32. (a) Wang, Y.-X.; Jacob, J.; Cordier, F.; Wingfield, P.; Stahl, S. J.; Lee Huang, S.; Torchia, D.; Grezeseik, S.; Bax, A. J. Biomol. NMR 1999, 14, 181.
33. (b) Lohr, F.; Mayhew, S. G.; Ruterjans, H. J. Am. Chem. Soc. 2000, 122, 9289.
34. Dingley, A. J.; Masse, J. E.; Feigon, J.; Grezeseik, S. J. Biomol. NMR 2000, 16, 279
35. Sychrovsky, V.; Vacek, J.; Hobza, P.; Zidek, L.; Sklenar, V.; Cremer, D. J. Phys. Chem. B 2002, 106, 10242.
36. (a) Scheurer, C.; Brüschweiler, R. J. Am. Chem. Soc. 1999, 121, 8661.
37. (b) Case, A.; Scheurer, C.; Brschweiler, R. J. Am. Chem. Soc. 2000, 122, 10390.
38. Pecul, M.; Sadlej, J. Chem. Phys. Lett. 1999, 308, 486.
39. Benedict, H.; Shenderovich, I. G.; Malkina, O. L.; Malkin, V.G.; Denisov, G. S.; Golubev, N. S.; Limbach, H. H. J. Am. Chem. Soc. 2000, 122, 1979.
40. Arnold, W. D.; Oldfield, E. J. Am. Chem. Soc. 2000, 122, 12835.
41. Bagno, A. Chem. Eur. J. 2000, 6, 2925.
42. (a) Del Bene, J. E.; Perera, S. A.; Bartlett, R. J. J. Am. Chem. Soc. 2000, 122, 3560.
43. (b) Del Bene, J. E.; Bartlett, R. J. J. Am. Chem. Soc. 2000, 122, 10480.
44. Del Bene, J. E.; Perera, S. A.; Bartlett, R. J. J. Phys. Chem. A 2001, 105, 930.
45. Wilkens, S. J.; Westler, W. M.; Weinhold, F.; Markley, J. L. J. Am. Chem. Soc. 2002, 121, 1601.
46. Barfield, M. J. Am. Chem. Soc. 2002, 124, 4158.
47. Alabugin, I. V.; Mancharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973.
48. (a) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887.
49. (b) Cleland, W. W.; Kreevoy, M. M. Science 1995, 269, 104.
50. Tobin, J. B.; Whitt, S. A.; Cassidy, C. S.; Frey, P. A. Biochemistry 1995, 34, 6919.
51. Garcia-Viloca, M.; Gelabert, R.; Gonzales-Lafort, A.; Moreno, M.; Llush, M. J. J. Phys. Chem. A 1997, 101, 8727.
52. Schiott, B.; Iversen, B. B.; Madsen, G. K. H.; Bruice, T. C. J. Am. Chem. Soc. 1998, 120, 12117.
53. Gräfenstein, J.; Wu, A.; Tuttle, T.; Cremer, D. Submitted for publication.
54. Wu, A.; Gräfenstein, J.; Cremer, D. J. Phys. Chem. A 2003 107, 7043.
55. Wu, A.; Cremer, D. Phys. Chem. Chem. Phys., in press.
56. Ramsey, N. F. Phys. Rev. 1953, 91, 303.
57. Sychrovsky, V.; Gräfenstein, J.; Cremer, D. J. Chem. Phys. 2000, 113, 3530.
58. (b) Helgaker, T.; Watson, M.; Handy, N. C. J. Chem. Phys. 2000, 113, 9402.
59. Boys, S. F. Rev. Mod. Phys. 1960, 32, 296.
60. Huber, K. P.; Herzberg, G. Molecular Spectra and Molecular Structure, IV. Constants of Diatomic Molecules; Van Nostrand: New York, 1979.
61. Cremer, D. Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds; Wiley: Chichester, 1998; Vol. 3, p 1706.
62. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
63. Dunning, T. H., Jr. J. Chem. Phys. 1989, 99, 107.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
65. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
66. (b) Lee, C.; Yang, W.; Parr, R. P. Phys. Rev. B 1988, 37, 785.
67. Kuetzelnigg, W.; Fleischer, U.; Schindler, M. In NMR-Basics Principles and Progress; Springer: Heidelberg, 1990; Vol. 23, p 165.
68. Berger, S.; Braun, S.; Kalinowski, H.-O. NMR Spectroscopy of the Non-Metallic Elements; Wiley: Chichester, U.K., 1997.
69. Boys, F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
70. COLOGNE2003, Kraka, E.; Gräfenstein, J.; Filatov, M.; He, Y.; Gauss, J.; Wu, A.; Polo, V.; Olsson, L.; Konkoli, Z.; He, Z.; Cremer, D. Göteborg University, Göteborg, 2003.
71. (a) Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1.
72. (b) Kowalewski, J. Annu. Rep. NMR Spectrosc. 1982, 12, 81.
73. 17O NMR Spectroscopy in Organic Chemistry; CRC Press: Boca Raton, FL, 1991.
74. Berger, S.; Braun, S.; Kalinowski, H.-O. NMR Spectroscopy of the Non-Metallic Elements; Wiley: Chichester, U.K., 1997.
75. (a) Kintzinger, J.-P. Oxygen NMR: Characteristic parameters and applications in NMR-17. Oxygen-17 and Silicon-29; Diehl, P., Fluck, E., Kosfield, R., Eds.; Springer Verlag: New York, 1981; p 1.
76. (b) Kintzinger, J.-P. In Oxygen-17 NMR; Laszlo, P., Ed.; NMR of Newly Accessible Nuclei, Vol. 2; Academic Press: New York, 1983; Chapter 4.
77. - anion or the allyl anion as a suitable reference. In these molecules the charge of the terminal atoms is 1.5, as that of the central atom 1 s or π electron. In the system O⋯H⋯N the charges should be about 1.60, 1, and 1.4 electrons in view of the electronegativity difference. Hence, a charge transfer of 0.4 electron from lp2(O) into the σ*(NH) orbital at an appropriate distance R(O,H) should lead to covalent bonding. Using this value as reference one obtains the percentages given in the text. Note that the one-orbital contributions always contain the repolarization effect, thus making an estimate of the covalent effect difficult.
78. (a) Carpenter, J. E.; Weinhold, F. J. Mol. Struct. (THEOCHEM) 1988, 169, 41.
79. (b) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
80. (c) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
81. Marchand, A. P. Stereochemical Application of NMR studies in Rigid Bicyclic Systems; VCH: Deerfield Beach, FL, 1982.
82. Tell, T.; Wu, A.; Kraka, E.; Cremer, D. To be published.
83. (a) Cremer, D.; Kraka, E. Angew. Chem. Int. Ed. Engl., 1984, 23, 62.
84. (b) Cremer, D.; Kraka, E. Croat. Chem. Acta 1984, 57, 1259.