Evidence for the participation of two distinct reactive intermediates in iron(III) porphyrin complex-catalyzed-epoxidation reactions

Journal of the American Chemical Society

Volumn 122, Issue 28, 2000, Pages 6641-6647

  Nam, Wonwoo ^a   Lim, Mi Hee ^a   Lee, Ha Jin ^a   Kim, Cheal ^b  

^a Ewha Womans University   (South Korea)

^b Seoul National University of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX; PORPHYRIN;

ARTICLE; BINDING COMPETITION; CATALYSIS; CHEMICAL REACTION KINETICS; EPOXIDATION; LIGAND BINDING; METAL BINDING;

EID: 0041082719     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000289k     Document Type: Article

References (79)

1. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
2. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
3. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
4. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
5. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
6. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
7. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
8. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
9. Reviews for heme-containing iron enzymes and iron porphyrin models: (a) McLain, J.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169. (b) Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221. (c) Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282. (d) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887. (e) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995. (f) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187. (g) Erman, J. E.; Hager, L. P.; Sligar, S. G. Adv. Inorg. Biochem. 1994, 10, 71-118. (h) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994. (i) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
10. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
11. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
12. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
13. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375-1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
14. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
15. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325-330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
16. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331-336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
17. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
18. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250-5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
19. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052- 7054.
20. Selected examples for nonheme iron enzymes and non-porphyrin iron complexes: (a) Choi, S.-Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. J. Am. Chem. Soc. 1999, 121, 12198-12199. (b) Chen, K.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2227-2229. (c) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887. (d) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375- 1376. (e) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331. (f) Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325- 330. (g) Lipscomb, J. D.; Que, L., Jr. J. Biol. Inorg. Chem. 1998, 3, 331- 336. (h) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624. (i) Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250- 5256. (J) Valentine, J. S.; Nam, W.; Ho, R. Y. N. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 183-198. (k) Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052-7054.
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