A first-principles quantum chemical study of coenzyme F430: Interplay of skeletal stereoisomerism and conformation in the stabilization of nickel(I)

Journal of the American Chemical Society

Volumn 122, Issue 27, 2000, Pages 6375-6381

  Wondimagegn, Tebikie ^a   Ghosh, Abhik ^a,b  

^a UNIVERSITY OF TROMSØ   (Norway)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL; NITROGEN; OXIDOREDUCTASE;

ARTICLE; CALCULATION; COENZYME; CONFORMATION; PREDICTION; QUANTUM CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 0034641232     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000648b     Document Type: Article

References (47)

1. Telser, J. Struct. Bonding 1998, 91, 31.
2. The term corphin describes a hybrid of a porphyrin-type C-N skeleton and corrin-type conjugation: Won, H.; Olson, K. D.; Summers, M. F.; Wolfe, R. S. Comments Inorg. Chem. 1993, 15, 1.
3. (a) DiMarco, A. A.; Bobik, T. A.; Wolfe, R. S. Annu. Rev. Biochem. 1990, 59, 355.
4. (b) Hartzell, P. L.; Wolfe, R. S. Syst. Appl. Microbiol. 1986, 7, 376.
5. (c) Wolfe, R. S. Annu. Rev. Microbiol. 1991, 45, 1.
6. Thauer, R. K. Microbiology 1998, 144, 2377.
7. Jaun, B. Helv. Chim. Acta 1990, 73, 2209.
8. Telser, J.; Horng, Y.-C.; Becker, D. F.; Hoffman, B. M.; Ragsdale, S. W. J. Am. Chem. Soc. 2000, 122, 182.
9. (a) Rospert, S. R.; Böcher, R.; Albracht, S. P. J.; Thauer, R. K. FEBS Lett. 1991, 291, 371.
10. (b) Rospert, S. R.; Voges, M.; Berkessel, A.; Albracht, S. P. J.; Thauer, R. K. Eur. J. Biochem. 1992, 210, 101.
11. (c) Albracht, S. P. J.; Ankel-Fuchs, D.; Böcher, R.; Ellermann, J.; Moll, J.; van der Zwaan, J. W.; Thauer, R. K. Biochim. Biophys. Acta 1986, 955, 86.
12. (d) Krzycki, J. A.; Prince, R. C. Biochim. Biophys. Acta 1990, 1015, 53.
13. (e) Jaun, B.; Pfaltz, A. J. Chem. Soc., Chem. Comm. 1986, 1327.
14. 430, see: (a) Holliger, C.; Pierik, A. J.; Reijerse, E. J.; Hagen, W. R. J. Am. Chem. Soc. 1993, 115, 5651. (b) Telser, J.; Fann, Y.-C.; Renner, M. W.; Fajer, J.; Wang, S.; Zhang, H.; Scott, R. A.; Hoffman, B. M. J. Am. Chem. Soc. 1997, 119, 733.
15. 430, see: (a) Holliger, C.; Pierik, A. J.; Reijerse, E. J.; Hagen, W. R. J. Am. Chem. Soc. 1993, 115, 5651. (b) Telser, J.; Fann, Y.-C.; Renner, M. W.; Fajer, J.; Wang, S.; Zhang, H.; Scott, R. A.; Hoffman, B. M. J. Am. Chem. Soc. 1997, 119, 733.
16. (a) Shelnutt, J. A.; Song, X.-Z.; Ma, J.-G.; Jia, S.-L.; Jentzen, W.; Medforth, C. J. Chem. Soc. Rev. 1998, 27, 31.
17. (b) Zimmer, M. J. Biomol. Struct. Dyn. 1993, 11, 203.
18. (c) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062.
19. For recent reviews of DFT studies of the molecular structures of porphyrins and metalloporphyrins, see: (a) Ghosh, A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic: New York, 2000; Vol 7, Chapter 47, pp 1-38. (b) Ghosh, A. Acc. Chem. Res. 1998, 31, 189.
20. For recent reviews of DFT studies of the molecular structures of porphyrins and metalloporphyrins, see: (a) Ghosh, A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic: New York, 2000; Vol 7, Chapter 47, pp 1-38. (b) Ghosh, A. Acc. Chem. Res. 1998, 31, 189.
21. (a) Vangberg, T.; Ghosh, A. J. Am. Chem. Soc. 1999, 121, 12154.
22. (b) Ghosh, A.; Gonzalez, E.; Vangberg, T. J. Phys. Chem. B 1999, 103, 1363.
23. (c) meso-Tetrakis(perfluoroalkyl)porphyrins: Wondimagegn, T.; Ghosh, A. J. Phys. Chem. B, submitted,
24. (d) Nickel and zinc complexes of hydroporphyrins and chlorophin: Wondimagegn, T.; Ghosh, A. J. Phys. Chem. B (Thomas G. Spiro Festschrift), in press.
25. Barkigia, K. M.; Fajer, J. In The Photosynthetic Reaction Center: Deisenhofer, J., Norris, J. R., Eds.; Academic Press: San Diego, 1993; Vol. 2, p 513.
26. Suh, M. P.; Swepston, P. N.; Ibers, J. A. J. Am. Chem. Soc. 1984, 106, 5164.
27. Brückner, C.; Sternberg, E. D.; MacAlpine, J. K.; Rettig, S. J.; Dolphin, D. J. Am. Chem. Soc. 1999, 121, 2609.
28. The ADF program is obtainable from: Scientific Computing and Modelling, Department of Theoretical Chemistry, Vrije Universiteit, 1081 HV Amsterdam, The Netherlands.
29. Convergence criteria for the geometry optimizations were 0.0001 hartrees for the molecular energy, 0.001 for gradients, 0.005 Å for bond distances, and 0.2° for angles.
30. Färber, G.; Keller, W.; Kratky, C.; Jaun, B.; Pfaltz, A.; Spinner, C.; Kobelt, A.; Eschenmoser, A. Helv. Chim. Acta 1991, 74, 697.
31. For a recent study on the stereochemical properties of molecular faces, see: Ghosh, A. Theor. Chem. Acc. 2000, in press.
32. Ozawa, S.; Watanabe, Y.; Morishima, I. Tetrahedron Lett. 1994, 35, 4141.
33. Kaplan, W. A.; Suslick, K. S.; Scott, R. A. J. Am. Chem. Soc. 1991, 113, 9824.
34. Ermler, U.; Grabarse, W.; Shima, S.; Goubeaud, M.; Thauer, R. K. Science 1997, 278, 1457.
35. Furenlid, L. R.; Renner, M. W.; Fajer, J. J. Am. Chem. Soc. 1990, 112, 8987.
36. (a) Renner, M. W.; Furenlid, L. R.; Stolzenberg, A. M. J. Am. Chem. Soc. 1995, 117, 293.
37. (b) Renner, M. W.; Furenlid, L. R.; Barkigia, K. M.; Forman, A.; Shim, H. K.; Simpson, D. J.; Smith, K. M.; Fajer, J. J. Am. Chem. Soc. 1991, 113, 6891.
38. Furenlid, L. R.; Renner, M. W.; Szalda, D. J.; Fujita, E. J. Am. Chem. Soc. 1991, 113, 883.
39. Shiemke, A. K.; Kaplan, W. A.; Hamilton, C. L.; Shelnutt, J. A.; Scott, R. A. J. Biol. Chem. 1989, 264, 7276.
40. Pfaltz, A.; Livinston, D. A.; Jaun, B.; Diekert, G.; Thauer, R. K.; Eschenmoser, A. Helv. Chim. Acta 1985, 68, 1338.
41. Keltjens, J. T.; Hermans, J. M. H.; Rijsdijk, G. J. F. A.; van der Drift, C.; Vogels, J. D. Antonie van Leeuwenhoek 1988, 54, 207.
42. Furenlid, L. R.; Renner, M. W.; Fajer, J. J. Am. Chem. Soc. 1990, 112, 8987.
43. Helvenston M. C.; Castro, C. E. J. Am. Chem. Soc. 1992, 114, 8490.
44. Seth, J.; Palaniappan, V.; Bocian, D. F. Inorg. Chem. 1995, 34, 2201.
45. Ghosh, A.; Wondimagegn, T.; Gonzalez, E.; Halvorsen, I. J. Inorg. Biochem. 2000, 78, 79.
46. (a) Brown, T. G.; Hoffman, B. M. Mol. Phys. 1980, 39, 1073.
47. (b) Ghosh, A.; Wondimagegn, T. Unpublished results.