Ab initio density functional theory calculations and vibrational analysis of zinc-bound 4-methylimidazole as a model of a histidine ligand in metalloenzymes

Journal of Physical Chemistry A

Volumn 106, Issue 14, 2002, Pages 3377-3390

  Hasegawa, Koji ^a   Ono, Taka Aki ^a   Noguchi, Takumi ^a  

^a RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HISTIDINE; METALLOENZYMES; METHYLLIMIDAZOLE; VIBRATIONAL ANALYSIS;

AMINO ACIDS; CATALYSIS; ENZYME KINETICS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR VIBRATIONS; PROBABILITY DENSITY FUNCTION; PROTEINS;

ZINC COMPOUNDS;

EID: 0037061931     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp012251f     Document Type: Article

References (58)

1. Sundberg, R. J.; Martin, R. B. Chem. Rev. 1974, 74, 471.
2. Regan, L. Annu. Rev. Biophys. Biomol. Struct. 1993, 22, 257.
3. Ascone, I.; Castaner, R.; Tarricone, C.; Bolognesi, M.; Stroppolo, M. E.; Desideri, A. Biochem. Biophys. Res. Commun. 1997, 241, 119.
4. Murphy, L. M.; Strange, R. W.; Hasnain, S. S. Structure 1997, 5, 371.
5. Wang, D.; Zhao, X.; Vargek, M.; Spiro, T. G. J. Am. Chem. Soc. 2000, 122, 2193.
6. Hashimoto, S.; Ono K.; Takeuchi, H. J. Raman Spectrosc. 1998, 29, 969.
7. Morgan, J. E.; Verkhovsky, M. I., Wikström, M. J. Bioenerg. Biomembr. 1994, 26, 599.
8. Wikström, M. Biochim. Biophys. Acta 2000, 1458, 188.
9. Garfinkel, D.; Edsall, J. T. J. Am. Chem. Soc. 1958, 80, 3807.
10. Bellocq, A. M.; Perchard, C.; Novak, A.; Josien, M. L. J. Chim. Phys. 1965, 62, 1334.
11. Lord, R. C.; Yu, N.-T. J. Mol. Biol. 1970, 51, 203.
12. Yoshida, C. M.; Freedman, T. B.; Loehr, T. M. J. Am. Chem. Soc. 1975, 97, 1028.
13. Salama, S.; Spiro, T. G. J. Am. Chem. Soc. 1978, 100, 1105.
14. Stein, P.; Mitchell, M.; Spiro, T. G. J. Am. Chem. Soc. 1980, 102, 7795.
15. Caswell, D. S.; Spiro, T. G. J. Am. Chem. Soc. 1986, 108, 6470.
16. Smulevich, G.; Mauro, J. M.; Fishel, L. A.; English, A. M.; Kraut, J.; Spiro, T. G. Biochemistry 1988, 27, 5477.
17. Zhao, X.; Wang, D.; Spiro, T. G. J. Am. Chem. Soc. 1998, 120, 8517.
18. Zhao, X.; Wang, D.; Spiro, T. G. Inorg. Chem. 1998, 37, 5414.
19. Vargek, M.; Zhao, X.; Lai, Z.; McLendon, G. L.; Spiro, T. G. Inorg. Chem. 1999, 38, 1372.
20. Zhao, X.; Chen, R.; Deng, Q.; Mabrouk, P. A.; Spiro, T. G. Isr. J. Chem. 2000, 40, 15.
21. Ashikawa, I.; Itoh, K. Biopolymers 1979, 18, 1859.
22. Itabashi, M.; Itoh, K. Chem. Lett. 1979, 1331.
23. Teraoka, J.; Kitagawa, T. J. Biol. Chem. 1981, 256, 3969.
24. Tasumi, M.; Harada, I.; Takamatsu, T.; Takahashi, S. J. Raman Spectrosc. 1982, 12, 149.
25. Chinsky, L.; Jolles, B.; Laigle, A.; Turpin, P. Y. J. Raman Spectrosc. 1985, 16, 235.
26. Asher, S. A.; Murtaugh, J. L. Appl. Spectrosc. 1988, 42, 83.
27. Hashimoto, S.; Ohsaka, S.; Takeuchi, H.; Harada, I. J. Am. Chem. Soc. 1989, 111, 8926.
28. Takeuchi, H.; Kimura, Y.; Koitabashi, I.; Harada, I. J. Raman Spectrosc. 1991, 22, 233.
29. Hashimoto, S.; Takeuchi, H. J. Am. Chem. Soc. 1998, 120, 11012.
30. Miura, T.; Satoh, T.; Hori-i, A.; Takeuchi, H. J. Raman Spectrosc. 1998, 29, 41.
31. Miura, T.; Satoh, T.; Takeuchi, H. Biochim. Biophys. Acta 1998, 1384, 171.
32. Miura, T.; Hori-i, A.; Mototani, H.; Takeuchi, H. Biochemistry 1999, 38, 11560.
33. Miura, T.; Suzuki, K.; Kohata, N.; Takeuchi, H. Biochemistry 2000, 39, 7024.
34. Berthomieu, C.; Boussac, A.; Mäntele, W.; Breton, J.; Nabedryk, E. Biochemistry 1992, 31, 11460.
35. Hienerwadel, R.; Berthomieu, C. Biochemistry 1995, 34, 16288.
36. Berthomieu, C.; Hienerwadel, R. Biochemistry 2001, 40, 4044.
37. Markham, L. M.; Mayne, L. C.; Hudson, B. S.; Zgierski, M. Z. J. Phys. Chem. 1993, 97, 10319.
38. Wellner, N.; Zundel, G. J. Mol. Struct. 1994, 317, 249.
39. Majoube, M.; Millié, Ph.; Vergoten, G. J. Mol. Struct. 1995, 344, 21.
40. Torreggiani, A.; Bonora, S.; Fini, G. Biopolymers 2000, 57, 352.
41. Noguchi, T.; Inoue, Y. J. Biochem. 1995, 118, 9.
42. Noguchi, T.; Inoue, Y.; Tang, X.-S. Biochemistry 1999, 38, 399.
43. Noguchi, T.; Kurrech, J.; Inoue, Y.; Renger, G. Biochemistry 1999, 38, 4846.
44. Noguchi, T.; Inoue, Y.; Tang, X.-S. Biochemistry 1999, 38, 10187.
45. Hasegawa, K.; Ono, T.; Noguchi, T. J. Phys. Chem. B 2000, 104, 4253.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
47. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
48. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
49. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 27.
50. Shimanouchi, T. Computer Programs of Normal Coordinate Treatment of Polyatomic Molecules; The University of Tokyo: Tokyo, Japan, 1968.
51. Yoshida, H.; Tasumi, M. J. Chem. Phys. 1988, 89, 2803.
52. Pulay, P.; Fogarasi, G.; Pang, F.; Boggs, J. E. J. Am. Chem. Soc. 1979, 101, 2550.
53. Basch, H.; Krauss, M.; Stevens, W. J. Int. J. Quantum Chem. 1987, XXXI, 405.
54. Cini, R.; Musaev, D. G.; Marzilli, L. G.; Morokuma, K. J. Mol. Struct.: THEOCHEM 1997, 392, 55.
55. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1 (in Gaussian 98); Gaussian, Inc.: Pittsburgh, PA, 1998.
56. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
57. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, 5th ed.; John Wiley & Sons: New York, 1997.
58. El Yazal, J.; Pang, Y.-P. J. Phys. Chem. B 1999, 103, 8773.