Catalase and epoxidation activity of manganese salen complexes bearing two xanthene scaffolds

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8192-8198

  Yang, Jenny Y ^a   Nocera, Daniel G ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; ELECTRON TRANSITIONS; EPOXIDATION; HYDROGEN PEROXIDE; STEREOCHEMISTRY;

CATALASES; ELECTRON TRANSFER; MACROCYCLES; PROTON-COUPLED ELECTRON TRANSFER (PCET); XANTHENE;

MANGANESE COMPOUNDS;

CATALASE; CYCLOHEXANE DERIVATIVE; DIAMINE DERIVATIVE; HYDROGEN PEROXIDE; LIGAND; MACROCYCLIC COMPOUND; MANGANESE DERIVATIVE; NAPHTHALENE DERIVATIVE; OXIDIZING AGENT; OXYGEN; WATER; XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; DEPROTECTION REACTION; ELECTRON TRANSPORT; ENANTIOMER; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SUZUKI REACTION;

CATALASE; ETHYLENEDIAMINES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; XANTHENES;

EID: 34447121484     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070358w     Document Type: Article

References (43)

1. Reece, S. Y.; Hodgkiss, J. M.; Stubbe, J.; Nocera, D. G. Philos. Trans. R. Soc. London, Ser. B 2006, 361, 1351-1364.
2. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
3. Yeh, D.-Y.; Chang, C. J.; Nocera, D. G. J. Am. Chem. Soc. 2001, 5, 1513-1514.
4. Chng, L. L.; Chang, C. J.; Nocera, D. G. Org. Lett. 2003, 5, 2421-2424.
5. Chang, C. J.; Chng, L. L.; Nocera, D. G. J. Am. Chem. Soc. 2003, 125, 1866-1876.
6. Liu, S.-Y.; Nocera, D. G. J. Am. Chem. Soc. 2005, 127, 5278-5279.
7. Yang, J. Y.; Bachmann, J.; Nocera, D. G. J. Org. Chem. 2006, 71, 8706-8714.
8. Yeh, C.-Y.; Chang, C. J.; Nocera, D. G. J. Am. Chem. Soc. 2001, 123, 1513-1514.
9. Chang, C. J.; Yeh, C.-Y.; Nocera, D. G. J. Org. Chem. 2002, 67, 1403-1406.
10. Liu, S.-Y.; Nocera, D. G. J. Am. Chem. Soc. 2005, 127, 5278-5279.
11. Doctrow, S. R.; Adinolfi, C.; Baudry, M.; Huffman, K.; Malfroy, B.; Marcus, C. B.; Melov, S.; Pong, K.; Rong, Y.; Smart, J. L.; Tocco, G. In Critical Reviews of Oxidative Stress and Aging: Advances in Basic Science, Diagnostics, and Intervention, Vol. 2; Cutler, R. G., Rodriquez, H., Eds.; World Scientific: Hackensack, NJ, 2003; pp 1324-1343.
12. Gonzalez, P. K.; Zhuang, J.; Doctrow, S. R.; Malfroy, B.; Benson, P. F.; Menconi, M. J.; Fink, M. P. J. Pharmacol. Exp. Ther. 1995, 275, 798-806.
13. McDonald, M. C.; d'Emmanuele di Villa Bianca, R.; Wayman, N. S.; Pinto, A.; Sharpe, M. A.; Cuzzocrea, S.; Chatterjee, P. K.; Thiemermann, C. Eur. J. Pharmacol. 2003, 466, 181-189.
14. Olcott, A. P.; Tocco, G.; Tian, J.; Zekzer, D.; Fukuto, J.; Ignarro, L.; Kaufman, D. L. Diabetes 2004, 53, 2574-2579.
15. Baker, K.; Marcus, C. B.; Huffman, K.; Kruk, H.; Malfroy, B.; Doctrow S. R. J. Pharmacol. Exp. Ther. 1998, 284, 215-221.
16. d'Emmanuele di Villa Bianca, R.; Wayman, N. S.; McDonald, M. C.; Pinto, A.; Sharpe, M. A.; Chatterjee, P. K.; Thiemermann, C. Med. Sci. Monit. 2002, 8, BR1-7.
17. Decraene, D.; Smaers, K.; Gan, D.; Mammone, T.; Matusi, M.; Maes, D.; Declercq, L.; Garmyn, M. J. Invest. Dermatol. 2004, 122, 484-491.
18. Doctrow, S. R.; Huffman, K.; Marcus, C. B.; Tocco, G.; Malfroy, E.; Adinolfi, C. A.; Kruk, H.; Baker, K.; Lazarowych, N.; Mascarenhas, J. J. Med. Chem. 2002, 45, 4549-4558.
19. Abashkin, Y. G.; Burt, S. K. J. Phys. Chem. B 2004, 108, 2708-2711.
20. Abashkin, Y. G.; Burt, S. K. Inorg. Chem. 2005, 44, 1425-1432.
21. Liu, S.-Y.; Soper, J. D.; Yang, J. Y.; Rybak-Akimova, E. V.; Nocera, D. G. Inorg. Chem. 2006, 45, 7572-7574.
22. Jacobsen, E. N.; Wu, M. H. Epoxidation of Alkenes Other than Allylic Alcohols. In Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; pp 649-677.
23. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
24. Cavazzini, M.; Manfredi, A.; Montanari, F.; Quici, S.; Pozzi, G. Eur. J. Org. Chem. 2001, 4639-4649.
25. Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813-9816.
26. Chang, C. J.; Yeh, C.-Y.; Nocera, D. G. J. Org. Chem. 2002, 67, 1403-1406.
27. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Infrared Spectroscopy. In Spectrometric Identification of Organic Compounds; Wiley: New York, 1991; p 118.
28. Nomura, Y.; Kubozono, T.; Hidaka, M.; Horibe, M.; Mizushima, N.; Yamamoto, N.; Takahashi, T.; Komiyama, M. Bioorg. Chem. 2004, 32, 26-37.
29. Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Sec. 1986, 108, 2309-2320.
30. Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416.
31. Khavrutskii, I. V.; Musaev, D. G.; Morokuma, K. Inorg. Chem. 2005, 44, 206-315.
32. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
33. Watanabe, Y. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 4, pp 97-117.
34. Veitch, N. C.; Smith, A. T. In Advances in Inorganic Chemistry; Academic Press: New York, 2001; Vol. 51, pp 107-162.
35. Poulos, T. L. In Advances in Inorganic Biochemistry; Eichhorn, G. L., Marzilli, L. G., Eds.; Elsevier: New York, 1988; Vol. 7, pp 1-36.
36. Dawson, J. H. Science 1988, 240, 433-439.
37. Soper, J. D.; Kryatov, S. V.; Rybak-Akimova, E. V.; Nocera, D. G. J. Am. Chem. Soc. 2007, 129, 5069-5075.
38. Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 1994, 255-256.
39. McGarrigle, E. M.; Gilheany, D. C. Chem. Rev. 2005, 105, 1563-1602.
40. Lin, G.-Q.; Li, Y.-M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley: New York, 2001; pp 237-249.
41. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4m ed.; Butterworth-Heinemann: Oxford, 1966.
42. Cavazzini, M.; Manfredi, A.; Montanari, F.; Quici, S.; Pozzi, G. Eur. J. Org. Chem. 2001, 24, 4639-4649.
43. Zheng, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296-2298.