External electric field will control the selectivity of enzymatic-like bond activations

Journal of the American Chemical Society

Volumn 126, Issue 37, 2004, Pages 11746-11749

  Shaik, Sason ^a   De Visser, Sam P ^a   Kumar, Devesh ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSTS; CHEMICAL BONDS; ELECTRIC FIELDS; HYDROXYLATION; MOLECULAR ORIENTATION; ORGANOMETALLICS; STEREOCHEMISTRY;

EPOXIDATION; HEME-ENZYMES; NONPOLAR BONDS;

CATALYST SELECTIVITY;

CARBON; HYDROGEN;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; ELECTRIC FIELD; ENZYME CHEMISTRY; ENZYME SPECIFICITY; EPOXIDATION; HYDROXYLATION;

BIOMIMETIC MATERIALS; ELECTRICITY; ENZYMES; EPOXY COMPOUNDS; HEMEPROTEINS; HYDROXYLATION; THERMODYNAMICS;

EID: 4544352396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047432k     Document Type: Article

References (33)

1. Loew, G. H.; Harris, D. L. Chem. Rev. 2000, 700, 407-419.
2. (a) Harris, D. L. Curr. Opin. Chem. Biol. 2001, 5, 724-735.
3. (b) Green, M. T. J. Am. Chem. Soc. 1999, 121, 7939-7340.
4. (c) Ogliaro, F.; de Visser, S. P.; Cohen, S.; Kaneti, J.; Shaik, S. ChemBioChem. 2001, 848-851.
5. Kaizer, J.; Klinker, E. J.; Oh, N. Y.; Rohde, J.-U.; Song, W. J.; Stubna, A.; Kim, J.; Münck, E.; Nam, W.; Que, L., Jr. J. Am. Chem. Soc. 2004, 726, 472-473.
6. Rohde, J.-U.; In, J.-H.; Lim, M. H.; Brennessel, W. W.; Bukowski, M. R.; Stubna, A.; Münck, E.; Nam, W.; Que, L., Jr. Science 2003, 299, 1037-1039.
7. Groves, J. T.; Shalyaev, K.; Lee, J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Chapter 27, pp 17-40.
8. Neuman, R.; Dahan, M. Nature 1997, 388, 353-355.
9. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450.
10. Ortiz de Montellano, P. R.; De Voss, J. J. Nat. Prod. Rep. 2002, 79, 1-18.
11. Groves, J. T.; Han, Y.-Z. in Cytochrome P450: Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; Chapter 1, pp 3-48.
12. Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
13. Woggon, W.-D. Top. Curr. Chem. 1996, 184, 40-96.
14. Schöneboom, J. C.; Lin, H.; Reuter, N.; Thiel, W.; Cohen, S.; Ogliaro, F.; Shaik, S. J. Am. Chem. Soc. 2002, 724, 8142-8151.
15. (a) Shaik, S.; de Visser, S. P.; Ogliaro, F.; Schwarz, H.; Schröder, D. Curr. Opin. Chem. Biol. 2002, 6, 556-567.
16. (b) Shaik, S.; Cohen, S.; de Visser, S. P.; Sharma, P. K.; Kumar, D.; Kozuch, S.; Ogliaro, F.; Danovich, D. Eur. J. Inorg. Chem. 2004, 207-226.
17. (a) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. Angew. Chem. Int. Ed. 2002, 41, 1947-1951.
18. (b) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11 809-11 826.
19. Groves, J. T.; Avaria-Neisser, G. E.; Fish, K. M.; Imachi, M.; Kuczkowski, R. L. J. Am. Chem. Soc. 1986, 108, 3837-3838.
20. Danciu, T.; Beckman, E. J.; Hancu, D.; Cochran, R. N.; Grey, R.; Hajnik, D. M.; Jewson, J. Angew. Chem., Int. Ed. 2003, 42, 1140-1142.
21. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
22. Treynor, T. P.; Boxer, S. G. J. Phys. Chem. A. 2004, 108, 1764-1778.
23. Yamanouchi, K. Science 2002, 295, 1659-1660.
24. Kono, H.; Koseki, S.; Fujimura, Y. J. Phys. Chem. A. 2001, 105, 5627-5636.
25. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
26. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
27. Hay, J. P.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
28. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
29. 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.; Baboul, A. G.; 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, Gaussian, Inc.: Pittsburgh, PA, 1998.
30. (a) Ogliaro, F.; Cohen, S.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 12 892-12 893.
31. (b) Ogliaro, F.; de Visser, S. P.; Groves, J. T.; Shaik, S. Angew. Chem., Int. Ed. 2001, 40, 2874-2878.
32. Poulos, T. L. J. Biol. Inorg. Chem. 1996, 1, 356-359.
33. Poulos, T. L. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guillard, R., Eds.; Academic Press: San Diego, 2000; Volume 4, pp 189-218.