Propene activation by the oxo-iron active species of taurine/α- ketoglutarate dioxygenase (TauD) enzyme. How does the catalysis compare to heme-enzymes?

Journal of the American Chemical Society

Volumn 128, Issue 30, 2006, Pages 9813-9824

  De Visser, Sam P ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSTS; HYDROGEN BONDS; HYDROXYLATION; PROPYLENE; REACTION KINETICS; THERMODYNAMICS;

C-H BONDS; EPOXIDATION MECHANISM; PROPENE OXYGENATION; TAURINE/Α-KETOGLUTARATE DIOXYGENASE (TAUD;

ENZYMES;

2 OXOGLUTARIC ACID; DIOXYGENASE; OXIDIZING AGENT; PROPYLENE; TAURINE;

ARTICLE; CATALYSIS; COMPETITIVE INHIBITION; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ENZYME ACTIVE SITE; ENZYME SUBSTRATE; EPOXIDATION; OXYGENATION; SULFOXIDATION; SURFACE PROPERTY; THERMODYNAMICS;

ALKENES; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; IRON; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; OXIDATION-REDUCTION; OXYGEN; PROTEIN CONFORMATION; SUBSTRATE SPECIFICITY;

EID: 33746604011     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061581g     Document Type: Article

References (75)

1. Ortiz de Montellano, P. R., Ed. Cytochrome P450: Structure, Mechanism and Biochemistry, 3rd ed.: Kluwer Academic/Plenum Publishers: New York, 2004.
2. (a) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
3. (b) Woggon, W.-D. Top. Curr. Chem. 1996, 184, 39-96.
4. (c) Groves, J. T. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3569-3574.
5. (d) Groves, J. T. Chapter 1 in ref 1. pp 1-43.
6. (a) Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, R. M.; Ringe, D.; Petsko, G. A.; Sligar, S. G. Science 2000, 287, 1615-1622.
7. (b) Loew, G. H.; Harris, D. L. Chem. Rev. 2000, 100, 407-419.
8. (c) Harris, D. L. Curr. Opin. Chem. Biol. 2001, 5, 724-735.
9. (d) Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947-3980.
10. (a) Dawson, J. H.; Holm, R. H.; Trudell, J. R.; Barth, G.; Linder, R. E.; Bunnenberg, E.; Djerassi, C.; Tang, S. C. J. Am. Chem. Soc. 1976, 98, 3707-3709.
11. (b) Poulos, T. L. J. Biol. Inorg. Chem. 1996, 1, 356-359.
12. (a) Berglund, G. I.; Carlsson, G. H.; Smith, A. T.; Szöke, H.; Henriksen, A.; Hajdu, J. Nature (London) 2002, 417, 463-468.
13. (b) Goodin, D. B.; McRee, D. E. Biochemistry 1993, 32, 3313-3324.
14. (a) Bugg, T. D. H. Tetrahedron 2003, 59, 7075-7101.
15. (b) Costas, M.; Mehn, M. P.; Jensen, M. P.; Que Jr., L. Chem. Rev. 2004, 104, 939-986.
16. (a) Makris, T. M.; Denisov, I.; Schlichting, I.; Sligar, S. G. Chapter 5 in ref 1, pp 149-181.
17. (b) Kumar, D.; Hirao, H.; de Visser, S. P.; Zheng, J.; Wang, D.; Thiel, W.; Shaik, S. J. Phys. Chem. B 2005, 109, 19946-19951.
18. (c) Shaik, S.; Kumar, D.; de Visser, S. P.; Altun, A.; Thiel, W. Chem. Rev. 2005, 105, 2279-2328.
19. See, e.g., (a) Choroba, O. W.; Williams, D. H.; Spencer, J. B. J. Am. Chem. Soc. 2000, 122, 5389-5390.
20. (b) Higgins, L. J.; Yan, F.; Liu, P.; Liu, H.-W.; Drennan, C. L. Nature (London) 2005, 437, 838-844.
21. See, for instance: (a) Trewick, S. C.; Henshaw, T. F.; Hausinger, R. P.; Lindahl, T.; Sedgwick, B. Nature (London) 2002, 419, 174-178.
22. (b) Falnes, P. Ø.; Johansen, R. F.; Seeberg, E. Nature (London) 2002, 419, 178-182.
23. (c) Duncan, T.; Trewick, S. C.; Koivisto, P.; Bates, P. A.; Lindahl, T.; Sedgwick, B. Proc. Natl. Acad. Sci. USA 2002, 99, 16660-16665.
24. (d) Aas, P. A.; Otterlei, M.; Falnes, P. Ø.; Vågbø, C. B.; Skorpen, F.; Akbari, M.; Sundheim, O.; Bjørås, M.; Slupphaug, G.; Seeberg, E.; Krokan, H. E. Nature (London) 2003, 421, 859-863.
25. (e) Mishina, Y.; Duguid, E. M.; He, C. Chem. Rev. 2006, 106, 215-232.
26. Solomon, E. I.; Brunold, T. C.; Davis, M. I.; Kemsley, J. N.; Lee, S.-K.; Lehnert, N.; Neese, F.; Skulan, A. J.; Yang, Y.-S.; Zhou, J. Chem. Rev. 2000, 100, 235-349.
27. Ryle, M. J. Hausinger, R. P. Curr. Opin. Chem. Biol. 2002, 6, 193-201.
28. Bollinger Jr., J. M.; Price, J. C.; Hoffart, L. M.; Barr, E. W.; Krebs, C. Eur. J. Inorg. Chem. 2005, 4245-4254.
29. Elkins, J. M.; Ryle, M. J.; Clifton, I. J.; Dunning Hotopp, J. C.; Lloyd, J. S.; Burzlaff, N. I.; Baldwin, J. E.; Hausinger, R. P.; Roach, P. L. Biochemistry 2002, 41, 5185-5192.
30. O'Brien, J. R.; Schuller, D. J.; Yang, V. S.; Dillard, B. D.; Lanzilotta, W. N. Biochemistry 2003, 42, 5547-5554.
31. Price, J. C.; Barr, E. W.; Tirupati, B.; Bollinger Jr., J. M.; Krebs, C. Biochemistry 2003, 42, 7497-7508.
32. Grzyska, P. K.; Ryle, M. J.; Monterosso, G. R.; Liu, J.; Ballou, D. P.; Hausinger, R. P. Biochemistry 2005, 44, 3845-3855.
33. Krebs, C.; Price, J. C.; Baldwin, J.; Saleh, L.; Green, M. T.; Bollinger Jr., J. M. Inorg. Chem. 2005, 44, 742-757.
34. Proshlyakov, D. A.; Henshaw, T. F.; Monterosso, G. R.; Ryle, M. J.; Hausinger, R. P. J. Am. Chem. Soc. 2004, 126, 1022-1023.
35. Price, J. C.; Barr, E. W.; Hoffart, L. M.; Krebs, C.; Bollinger Jr., J. M. Biochemistry 2005, 44, 8138-8147.
36. (a) Ryle, M. J.; Koehntop, K. D.; Liu, A.; Que Jr., L.; Hausinger, R. P. Proc. Natl. Acad. Sci., U.S.A. 2003, 100, 3790-3795.
37. (b) Koehntop, K. D.; Marimanikkupam, S.; Ryle, M. J.; Hausinger, R. P.; Que Jr., L. J. Biol. Inorg. Chem. 2006, 11, 63-72.
38. (a) Decker, A.; Solomon, E. I. Angew. Chem., Int. Ed. 2005, 44, 2252-2255.
39. (b) Kumar, D.; Hirao, H.; Que Jr., L.; Shaik, S. J. Am. Chem. Soc. 2005, 127, 8026-8027.
40. de Visser, S. P. Angew. Chem., Int. Ed. 2006, 45, 1790-1793.
41. (a) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. Angew. Chem., Int. Ed. 2002, 41, 1947-1951.
42. (b) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809-11826.
43. Kumar, D.; de Visser, S. P.; Sharma, P. K.; Derat, E.; Shaik, S. J. Biol. Inorg. Chem. 2005, 10, 181-189.
44. Shaik, S.; de Visser, S. P.; Kumar, D. J. Am. Chem. Soc. 2004, 126, 11746-11749.
45. de Visser, S. P. J. Phys. Chem. A 2005, 109, 11050-11057.
46. Green, M. T. J. Am. Chem. Soc. 2000, 122, 9495-9499.
47. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
48. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
49. Hay, J. P.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
50. Jaguar 5.5; Schrödinger. Inc.: Portland OR, 2000.
51. Initially, we attempted to calculate the reaction profile with one atom of each ligand bound to iron fixed in position so that the structure matches the IOS7 pdb. However, this created technical problems with frequency calculations with several imaginary modes. Therefore, we subsequently removed all constraints from the geometries and did full geometry optimizations in Jaguar 5.5. Previous theoretical studies ((a) Siegbahn, P. E. M. Q. Rev. Biophys. 2003, 36, 91-145.
52. -1 between the fully optimised structure and a constraint one.
53. Frisch, M. J. et al., Gaussian-98, Gaussian, Inc., full reference see Supporting Information.
54. Ogliaro, F.; Harris, N.; Cohen, S.; Filatov, M.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 8977-8989.
55. (a) Bassan, A.; Borowski, T.; Siegbahn, P. E. M. Dalton Trans. 2004, 3153-3162.
56. (b) Borowski, T.; Bassan, A.; Siegbahn, P. E. M. Chem.-Eur. J. 2004, 10, 1031-1041.
57. Shiota, Y.; Yoshizawa, K. J. Phys. Chem. B 2004, 108, 17226-17237.
58. Andreoletti, P.; Pernoud, A.; Sainz, G.; Gouet, P.; Jouve, H. M. Acta Cryst. D 2003, 59, 2163-2168.
59. de Visser, S. P.; Shaik, S.; Sharma, P. K.; Kumar, D.; Thiel, W. J. Am. Chem. Soc. 2003, 125, 15779-15788.
60. Groves, J. T.; McClusky, G. A. J. Am. Chem. Soc. 1976, 98, 859-861.
61. Price, J. C.; Barr, E. W.; Glass, T. E.; Krebs, C.; Bollinaer, Jr.; J. M. J. Am. Chem. Soc. 2003, 125, 13008-13009.
62. Kumar, D.; de Visser, S. P.; Shaik, S. Chem.-Eur. J. 2005, 11, 2825-2835.
63. de Visser, S. P. J. Biol. Inorg. Chem. 2006, 11, 168-178.
64. Shaik, S.; de Visser, S. P.; Ogliaro, F.; Schwartz, H.; Schröder, D. Curr. Opin. Chem. Biol. 2002, 6, 556-567.
65. (a) de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2003, 125, 7413-7424.
66. (b) Sharma, P. K.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2003, 125, 8698-8699.
67. (c) Kumar, D.; de Visser, S. P.; Sharma, P. K.; Cohen, S.; Shaik, S. J. Am. Chem. Soc. 2004, 126, 1907-1920.
68. (d) de Visser, S. P.; Kumar, D.; Shaik, S. J. Inorg. Biochem. 2004, 98, 1183-1193.
69. (e) Kumar, D.; de Visser, S. P.; Sharma, P. K.; Hirao, H.; Shaik, S. Biochemistry 2005, 44, 8148-8158.
70. de Visser, S. P.; Ogliaro, F.; Shaik, S. Angew. Chem., Int. Ed. 2001, 40, 2871-2874.
71. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450.
72. Kaizer, J.; Klinker, E. J.; Oh, N. Y.; Rohde, J.-U.; Song, W. J.; Stubna, A.; Kim, J.; Münck, E.; Nam, W.; Que Jr., L. W. J. Am. Chem. Soc. 2004, 126, 472-473.
73. de Visser, S. P.; Kumar, D.; Cohen, S.; Shacham, R.; Shaik, S. J. Am. Chem. Soc. 2004, 126, 8362-8363.
74. Kumar, D.; Derat, E.; Khenkin, A. M.; Neumann, R.; Shaik, S. J. Am. Chem. Soc. 2005, 127, 17712-17718.
75. Shaik, S.; Shurki, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 586-625.