C-H activation by a mononuclear manganese(III) hydroxide complex: Synthesis and characterization of a manganese-lipoxygenase mimic?

Journal of the American Chemical Society

Volumn 127, Issue 27, 2005, Pages 9904-9912

  Goldsmith, Christian R ^a   Cole, Adam P ^a   Stack, T Daniel P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACIDS; MANGANESE; SUBSTRATES; THERMODYNAMIC PROPERTIES;

ALKYL PEROXIDES; C-H ACTIVATION; IRON COMPLEX; LIPOXYGENASES; MONONUCLEAR MANGANESE (III)HYDROXIDE COMPLEX; THERMODYNAMIC ANALYSIS;

ACTIVATION ANALYSIS;

LIPOXYGENASE; MANGANESE DERIVATIVE; MANGANESE HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DISSOCIATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

BIOMIMETIC MATERIALS; BIOMIMETICS; CARBON; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS; HYDROGEN; HYDROXIDES; LIPOXYGENASE; MANGANESE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 22144433689     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039283w     Document Type: Article

References (57)

1. Nelson, M. J.; Seitz, S. In Active Oxygen in Biochemistry: Valentine. J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Chapman and Hall: Glasgow, U.K., 1995; pp 276-312.
2. Su, C.; Oliw, E. J. Biol. Chem. 1998, 273, 13072-13079.
3. Hamberg, M.; Su, C.; Oliw, E. J. Biol. Chem. 1998, 273, 13080-13088.
4. Su, C.; Sahlin, M.; Oliw, E. H. J. Biol. Chem. 2000, 275, 18830-18835.
5. Glickman, M. H.; Klinman, J. P. Biochemistry 1995, 34, 14077-14092.
6. Segraves, E. N.; Holman, T. R. Biochemistry 2003, 42, 5236-5243.
7. Minor, W.; Steczko, J.; Stec, B.; Otwinowski, Z.; Bolin, J. T.; Walter, R.; Axelrod, B. Biochemistry 1996, 35, 10687-10701.
8. Skrzypczak-Jankun, E.; Amzel, L. M.; Kroa, B. A.; Funk, M. O., Jr. Proteins: Struct., Funct., Genet. 1997, 29, 15-31.
9. Boyington, J. C.; Gaffney, B. J.; Amzel, L. M. Science 1993, 260, 1482-1486.
10. Gillmor, S. A.; Villaseñor, A.; Fletterick, R.; Sigal, E.; Browner, M. F. Nat. Struct. Biol. 1997, 4, 1003-1009.
11. Sigal, E.; Craik, C. S.; Highland, E.; Grunberger, D.; Costello, L. L.; Dixon, R. A. F.; Nadel, J. A. Biochem. Biophys. Res. Commun. 1988, 157, 457-464.
12. Jisaka, M.; Kim, R. B.; Boeglin, W. E.; Nanney, L. B.; Brash, A. R. J. Biol. Chem. 1997, 272, 24410-24416.
13. Hörnsten, L.; Su, C.; Osbourn, A. E.; Hellman, U.; Oliw, E. H. Eur. J. Biochem 2002, 269, 2690-2697.
14. Lah, M. S.; Dixon, M. M.; Pattridge, K. A.; Stallings, W. C.; Fee, J. A.; Ludwig, M. L. Biochemistry 1995, 34, 1646-1660.
15. Maliekal, J.; Karapetian, A.; Vance, C.; Yikilmaz, E.; Wu, Q.; Jackson, T.; Brunold, T. C.; Spiro, T. G.; Miller, A.-F. J. Am. Chem. Soc. 2002, 124, 15064-15075.
16. Renault, J. P.; Verchère-Béaur, C.; Morgenstern-Badarau, I.; Yamakura, F.; Gerloch, M. Inorg. Chem. 2000, 39, 2666-2675.
17. Yikilmaz, E.; Xie, J.; Brunold, T. C.; Miller, A.-F. J. Am. Chem. Soc. 2002, 124, 3482-3483.
18. Vance, C. K.; Miller, A.-F. Biochemistry 2001, 40, 13079-13087.
19. Schenk, G.; Neidig, M. L.; Zhou, J.; Holman, T. R.; Solomon, E. I. Biochemistry 2003, 42, 7294-7302.
20. Scarrow, R. C.; Trimitsis, M. G.; Buck, C. P.; Grove, G. N.; Cowling, R. A.; Nelson, M. J. Biochemistry 1994, 33, 15023-15035.
21. Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624.
22. Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 8566-8567.
23. Goldsmith, C. R.; Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 124, 83-96.
24. Klein Gebbink, R. J. M.; Jonas, R. T.; Goldsmith, C. R.; Stack, T. D. P. Inorg. Chem. 2002, 41, 4633-4641.
25. Hubin, T. J.; McCormick, G. J.; Collinson, S. R.; Buchalova, M.; Perkins, C. M.; Alcock, N. W.; Kahol, P. K.; Raghunathan, A.; Busch, D. H. J. Am. Chem. Soc. 2000, 122, 2512-2522.
26. Wittmann, H.; Raab, V.; Schorm, A.; Plackmeyer, J.; Sundermeyer, J. Eur. J. Inorg. Chem. 2001, 8, 1937-1948.
27. deVries, M. E.; LaCrois, R. M.; Roelfes, G.; Kooijman, H.; Spek, A. L.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 1549-1550.
28. Goldsmith, C. R.; Jonas, R. T.; Cole, A. P.; Stack, T. D. P. Inorg. Chem. 2002, 41, 4642-4652.
29. The labeling schemes for 1 and 2 are congruent with previously reported PY5 structures.
30. Gupta Sreerama, S.; Pal, S.; Pal, S. Inorg. Chem. Commun. 2001, 4, 656-660.
31. Shonswe, M. S.; Mikuriya, M.; Ainscough, E. W.; Brodie, A. M. J. Chem. Soc., Chem. Commun, 1994, 7, 887-888.
32. Hubin, T. J.; McCormick, J. M.; Alcock, N. W.; Busch, D. H. Inorg. Chem. 2001, 40, 435-444.
33. Eichhorn, D. M.; Armstrong, W. H. J. Chem. Soc., Chem. Commun. 1992, 85-87.
34. Gupta, R.; MacBeth, C. E.; Young, V. G., Jr.; Borovik, A. S. J. Am. Chem. Soc. 2002, 124, 1136-1137.
35. Evans, D. F. J. Chem. Soc. 1959, 2003-2005.
36. See Supporting Information.
37. Bordwell, F. G.; Cheng, J. P.; Harrelson, J. A., Jr. J. Am. Chem. Soc. 1988, 110, 1229-1231.
38. Wang, K.; Mayer, J. M. J. Am. Chem. Soc. 1997, 119, 1470-1471.
39. Pedulli, G. F.; Lucarini, M.; Pedrielli, P.; Cabiddu, S.; Fattuoni, C. J. Org. Chem. 1996, 61, 9259-9263.
40. Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X. J. Am. Chem. Soc. 1991, 113, 9790-9795.
41. Rossi, M. J.; McMillen, D. F.; Golden, D. M. J. Phys. Chem. 1984, 88, 5031-5039.
42. Horner, O.; Anxolabéhère-Mallart, E.; Charlot, M.-F.; Tchertanov, J. G.; Mattioli, T. A.; Boussac, A.; Girerd, J.-J. Inorg. Chem. 1999, 38, 1222-1232.
43. Balland, V.; Banse, F.; Anxolabéhère-Mallart, E.; Ghiladi, M.; Mattioli, T. A.; Philouze, C.; Blondin, G.; Girerd, J.-J. Inorg. Chem. 2003, 42, 2470-2477.
44. Salah, N. B.; Mhalla, F. M. J. Electroanal Chem. 2000, 485, 42-48.
45. Bard, A. J. Encyclopedia of Electrochemistry of the Elements; Marcel Dekker: New York, 1978; Vol. 11.
46. Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567-3577.
47. Gardner, K. A.; Kuehnert, L. L.; Mayer, J. M. Inorg. Chem. 1997, 368, 2069-2078.
48. Bryant, J. R.; Mayer, J. M. J. Am. Chem. Soc. 2003, 125, 10351-10361.
49. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9-16.
50. Guthrie, J. P. J. Am. Chem. Soc. 1997, 119, 1151-1152.
51. Roth, J. P.; Yoder, J. C.; Won, T.-J.; Mayer, J. M. Science 2001, 294, 2524-2526.
52. Deng, Y.; Burns, J. H.; Moyer, B. A. Inorg. Chem. 1995, 34, 209-213.
53. Zuman, P.; Meites, L. Electrochemical Data; John Wiley & Sons: New York, 1974; Vol. A.
54. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Birmingham: 1974; Vol. IV.
55. Creagh, D. C.; McAuley, W. J. In International Tables for Crystallography, Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, 1992; Vol. C, pp 219-222, Table 214.212.216.218.
56. Creagh, D. C.; Hubbell, J. H. In International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, 1992; Vol. C, p 200-206 Table 204.202.204.203.
57. Kolthoff, I. M.; Chantooni, M. K., Jr.; Bhowmik, S. Anal Chem. 1967, 39, 315-320.