Computational modeling of standard reduction potentials of B12 cofactors

International Journal of Quantum Chemistry

Volumn 113, Issue 4, 2013, Pages 479-488

  Kumar, Manoj ^a   Galezowski, Wlodzimierz ^b   Kozlowski, Pawel M ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

AdoCbl; B12 cofactors; electrochemistry; MeCbl; reduction potential

Indexed keywords

ADENOSYLCOBALAMIN; ADOCBL; AXIAL LIGAND; COFACTORS; COMPUTATIONAL MODELING; DESCRIPTORS; DIMETHYLFORAMIDE; ELECTRON-DONATING; ELECTRONIC NATURES; ELECTRONIC STRUCTURE CALCULATIONS; ELECTRONWITHDRAWING; EXPERIMENTAL VALUES; FLUORINATED LIGANDS; FUNCTIONALS; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MECBL; POLARIZABLE CONTINUUMS; REDUCTION POTENTIAL; REPRODUCIBILITIES; STANDARD REDUCTION POTENTIALS;

DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRONIC STRUCTURE; EXPERIMENTS; LIGANDS; MOLECULAR ORBITALS;

REDUCTION;

EID: 84872975663     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.24155     Document Type: Article

References (68)

1. 12; Wiley: New York, 1999.
2. R. G. Matthews, Acc. Chem. Res. 2001, 34, 681.
3. R. Banerjee, S. W. Ragsdale, Annu. Rev. Biochem. 2003, 72, 209.
4. K. L. Brown, Chem. Rev. 2005, 105, 2075.
5. R. G. Matthews, In Metal Ions in Life Sciences, A. Sigel, H. Sigel, R. K. O. Sigel, Eds.; Royal Society of Chemistry: Cambridge, UK, 2009; Vol. 6, p. 53.
6. L. Randaccio, S. Geremia, N. Demitri, J. Wuerges, Molecules 2010, 15, 3228.
7. D. Lexa, J.-M. Savéant, J. Am. Chem. Soc. 1978, 100, 3220.
8. D. Lexa, J.-M. Savéant, Acc. Chem. Res. 1983, 16, 235.
9. R. L. Birke, Q. Huang, T. Spataru, D. K. Gosser, Jr., J. Am. Chem. Soc. 2006, 128, 1922.
10. T. Spataru, R. L. Birke, J. Electroanal. Chem. 2006, 593, 74.
11. P. M. Kozlowski, J. Kuta, W. Galezowski, J. Phys. Chem. B 2007, 111, 7638.
12. W. Galezowski, J. Kuta, P. M. Kozlowski, J. Phys. Chem. B 2008, 112, 3177.
13. R. G. Finke, B. D. Martin, J. Inorg. Biochem. 1990, 40, 19.
14. B. D. Martin, R. G. Finke, J. Am. Chem. Soc. 1992, 114, 585.
15. M. Kumar, P. M. Kozlowski, J. Phys. Chem. B 2009, 113, 9050.
16. P. M. Kozlowski, T. Kamachi, M. Kumar, T. Nakayama, K. Yoshizawa, J. Phys. Chem. B 2010, 114, 5928.
17. C. L. Drennan, S. Huang, J. T. Drummond, R. G. Mathews, M. L. Ludwig, Science 1994, 266, 1669.
18. F. Mancia, N. H. Keep, A. Nakagawa, P. F. Leadlay, S. McSweeney, B. Rasmussen, P. Bosecke, O. Diat, P. R. Evans, Struct. 1996, 4, 339.
19. A. D. Becke, J. Chem. Phys. 1986, 84, 4524.
20. J. P. Perdew, Phys. Rev. B 1986, 33, 8822.
21. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
22. K. P. Jensen, U. Ryde, J. Phys. Chem. A 2003, 107, 7539.
23. J. Kuta, S. Patchkovskii, M. Z. Zgierski, P. M. Kozlowski, J. Comp. Chem. 2006, 27, 1429.
24. P. M. Kozlowski, T. Kamachi, T. Toraya, K. Yoshizawa, Angew. Chem. Int. Ed. 2007, 46, 980.
25. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
26. S. Grimme, J. Comp. Chem. 2006, 27, 1787.
27. J. P. Perdew, J. A. Chevary, S. H. Vosko, K. A. Jackson, M. R. Pederson, D. J. Singh, C. Fiolhais, Phys. Rev. B 1992, 46, 6671.
28. J. P. Perdew, J. A. Chevary, S. H. Vosko, K. A. Jackson, M. R. Pederson, D. J. Singh, C. Fiolhais, Phys. Rev. B 1993, 48, 4978.
29. J. P. Perdew, K. Burke, Y. Wang, Phys. Rev. B 1996, 54, 16533.
30. J. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
31. J. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396.
32. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158.
33. C. Adamo, V. Barone, J. Chem. Phys. 1998, 108, 664.
34. P. E. M. Siegbahn, M. R. A. Blomberg, S.-L. Chen, J. Chem. Theory Comput. 2010, 6, 2040.
35. S.-L. Chen, M. R. A. Blomberg, P. E. M. Siegbahn, J. Phys. Chem. B 2011, 115, 4066.
36. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 109, 2999.
37. M. J. Frisch, et al. Gaussian 03, revision C.02, Gaussian, Inc., Wallingford, CT, 2003.
38. M. J. Frisch, et al. Gaussian 09, revision C.02, Gaussian, Inc., Wallingford, CT, 2009.
39. S. Trasatti, Pure Appl. Chem. 1986, 58, 955.
40. A. Lewis, J. A. Bumpus, D. G. Truhlar, C. J. Cramer, J. Chem. Educ. 2004, 81, 596.
41. A. Lewis, J. A. Bumpus, D. G. Truhlar, C. J. Cramer, J. Chem. Educ. 2007, 84, 934.
42. A. J. Bard, L. R. Faulkner, Electrochemical Methods; Wiley: New York, 1980.
43. K. Fujii, J. H. Galivan, F. M. Huennekens, Arch. Biochem. Biophys. 1977, 178, 662.
44. R. T. Taylor, H. Weisbach, J. Biol. Chem. 1967, 242, 1502.
45. D. M. Hoover, J. T. Jarrett, R. H. Sands, W. R. Dunham, M. L. Ludwig, R. G. Matthews, Biochemistry 1997, 36, 127.
46. M. D. Liptak, S. Datta, R. G. Matthews, T. C. Brunold, J. Am. Chem. Soc. 2008, 130, 16374.
47. M. Koutmos, S. Datta, K. A. Pattridge, J. L. Smith, R. G. Matthews, Proc. Natl. Acad. Sci. USA 2009, 106, 18527.
48. M. D. Liptak, T. C. Brunold, J. Am. Chem. Soc. 2006, 128, 9144.
49. D.-L. Zhou, O. Tinembart, R. Scheffold, L. Walder, Helv. Chim. Acta 1990, 73, 2225.
50. O. Tinembart, L. Walder, R. Scheffold, B. Bunsenges, Phys. Chem. 1988, 92, 1225.
51. R. Scheffold, S. Albrecht, R. Orlinski, H.-R. Ruf, P. Stamouli, O. Tinembart, L. Walder, C. Weymuth, Pure Appl. Chem. 1987, 59, 363.
52. P. Zuman, Substitutent Effects in Organic Polarography; Plenum: New York, 1967.
53. H. P. C. Hogenkamp, S. Holmes, Biochemistry 1970, 9, 1886.
54. C. P. Andrieux, I. Gallardo, J.-M. Savéant, J. Am. Chem. Soc. 1989, 111, 1620.
55. A. M. Calafat, L. G. Marzilli, J. Am. Chem. Soc. 1993, 111, 9182.
56. J. Kuta, J. Wuerges, L. Randaccio, P. M. Kozlowski, J. Phys. Chem. A 2009, 113, 11604.
57. R. E. Shepherd, S. Zhang, C. Goiygong, B. Wilk, S.-C. Choi, Inorg. Chim. Acta 1990, 174, 249.
58. R. Guilard, K. M. Kadish, Chem. Rev. 1988, 88, 1121.
59. A. Qiu, D. T. Sawyer, J. Porphyr,. Phthalocyanines 1997, 1, 125.
60. J. H. Grate, G. N. Schrauzer, J. Am. Chem. Soc. 1979, 101, 4601.
61. D. C. Woska, Z. D. Xie, A. A. Gridnev, S. D. Ittel, M. Fryd, B. B. Wayland, J. Am. Chem. Soc. 1996, 118, 9102.
62. A. A. Gridnev, S. D. Ittel, M. Fryd, B. B. Wayland, Organometallics 1993, 101, 4871.
63. N. Isaacs, Physical Organic Chemistry, 2nd ed.; Longman: Essex, England, 1995.
64. J.-E. Dubois, G. Mouvier, Tetrahedron Lett. 1963, 4, 1325.
65. D. P. White, J. C. Anthony, A. D. Oyefeso, J. Org. Chem. 1999, 64, 7707.
66. M. S. A. Hamza, X. Zou, K. L. Brown, R. van Eldik, Eur. J. Inorg. Chem. 2003, 2, 268.
67. P. W. Kenny, J. Chem. Soc. Perkin Trans. 1995, 2, 907.
68. S. Okazaki, M. Oyama, S. Nomura, Electroanalysis 1997, 9, 1242.