Dioxygen-initiated oxidation of heteroatomic substrates incorporated into ancillary pyridine ligands of carboxylate-rich diiron(II) complexes

Inorganic Chemistry

Volumn 45, Issue 2, 2006, Pages 837-848

  Carson, Emily C ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; IRON; LIGAND; ORGANOMETALLIC COMPOUND; OXYGEN; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ISOLATION AND PURIFICATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CARBOXYLIC ACIDS; CRYSTALLOGRAPHY, X-RAY; IRON; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; PYRIDINES; STEREOISOMERISM;

EID: 31644434018     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic051476s     Document Type: Article

References (69)

1. Erwin, D. P.; Erickson, I. K.; Delwiche, M. E.; Colwell, F. S.; Strap, J. L.; Crawford, R. L. Appl. Environ. Microbiol. 2005, 71, 2016-2025.
2. Vardar, G.; Wood, T. K. Appl. Environ. Microbiol. 2004, 70, 3253-3262.
3. Colby, J.; Stirling, D. I.; Dalton, H. Biochem. J. 1977, 165, 395-402.
4. Green, J.; Dalton, H. J. Biol. Chem. 1989, 264, 17698-17703.
5. Fox, B. G.; Borneman, J. G.; Wackett, L. P.; Lipscomb, J. D. Biochemistry 1990, 29, 6419-6427.
6. Fuse, H.; Ohta, M.; Takimura, O.; Murakami, K.; Inoue, H.; Yamaoka, Y.; Oclarit, J. M.; Omori, T. Biosci. Biotechnol. Biochem. 1998, 62, 1925-1931.
7. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759-805.
8. Wallar, B. J.; Lipscomb, J. D. Chem. Rev. 1996, 96, 2625-2657.
9. Merkx, M.; Kopp, D. A.; Sazinsky, M. H.; Blazyk, J. L.; Müller, J.; Lippard, S. J. Angew. Chem., Int. Ed. 2001, 40, 2782-2807.
10. Baik, M.-H.; Newcomb, M.; Friesner, R. A.; Lippard, S. J. Chem. Rev. 2003, 103, 2385-2419.
11. Kryatov, S. V.; Rybak-Akimova, E. V. Chem. Rev. 2005, 105, 2175-2226 and references therein.
12. Que, L., Jr.; Dong, Y. Acc. Chem. Res. 1996, 29, 190-196.
13. Que, L., Jr. J. Chem. Soc., Dalton Trans. 1997, 3933-3940.
14. Du Bois, J.; Mizoguchi, T. J.; Lippard, S. J. Coord. Chem. Rev. 2000, 200-202, 443-485.
15. Lippard, S. J. Chem. Br. 1986, 22, 221-228.
16. Lippard, S. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 344-361.
17. Lee, D.; Sorace, L.; Caneschi, A.; Lippard, S. J. Inorg. Chem. 2001, 40, 6774-6781.
18. Mandal, S. K.; Young, V. G., Jr.; Que, L., Jr. Inorg. Chem. 2000, 39, 1831-1833.
19. Herold, S.; Lippard, S. J. J. Am. Chem. Soc. 1997, 119, 145-156.
20. Goldberg, D. P.; Telser, J.; Bastos, C. M.; Lippard, S. J. Inorg. Chem. 1995, 34, 3011-3024.
21. Lee, D.; Lippard, S. J. Inorg. Chem. 2002, 41, 2704-2719.
22. Tolman, W. B.; Que, L., Jr. J. Chem. Soc., Dalton Trans. 2002, 653-660.
23. Tshuva, E. Y.; Lippard, S. J. Chem. Rev. 2004, 104, 987-1012.
24. Lee, D.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 4611-4612.
25. Lee, D.; Lippard, S. J. Inorg. Chem. 2002, 41, 827-837.
26. Yoon, S.; Lippard, S. J. Inorg. Chem. 2003, 42, 8606-8608.
27. (a) Carson, E. C.; Lippard, S. J. J. Inorg. Biochem. In press.
28. (b) Carson, E. C.; Lippard, S. J. Inorg. Chem. 2006, 2, 828-836.
29. Carson, E. C.; Lippard, S. J. J. Am. Chem. Soc. 2004, 126, 3412-3413.
30. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
31. Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341-6348.
32. Newkome, G. R.; Hager, D. C. J. Org. Chem. 1978, 43, 947-949.
33. SMART, version 5.626; Bruker AXS: Madison, WI, 2000.
34. Kuzelka, J.; Mukhopadhyay, S.; Spingler, B.; Lippard, S. J. Inorg. Chem. 2003, 42, 6447-6457.
35. Sheldrick, G. M. SHELXTL97-2: Program for Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
36. SHELXTL, version 5.10; Bruker AXS: Madison, WI, 1998.
37. Sheldrick, G. M. SADABS: Area-Detector Absorption Correction; University of Göttingen: Göttingen, Germany, 1996.
38. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 1998.
39. Kent, T. A. WMOSS, version 2.5; WEB Research Co.: Minneapolis, MN, 1998.
40. Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6th ed.; John Wiley & Sons: New York, 1998.
41. Münck, E. In Physical Methods in Bioinorganic Chemistry: Spectroscopy and Magnetism; Que, L., Jr., Ed.; University Science Books: Sausalito, CA, 2000; pp 287-319.
42. Chavez, F. A.; Ho, R. Y. N.; Pink, M.; Young, V. G., Jr.; Kryatov, S. V.; Rybak-Akimova, E. V.; Andres, H.; Münck, E.; Que, L., Jr.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 149-152.
43. Costas, M.; Cady, C. W.; Kryatov, S. V.; Ray, M.; Ryan, M. J.; Rybak-Akimova, E. V.; Que, L., Jr. Inorg. Chem. 2003, 42, 7519-7530.
44. Whittington, D. A.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 827-838.
45. Elango, N.; Radhakrishnan, R.; Froland, W. A.; Wallar, B. J.; Earhart, C. A.; Lipscomb, J. D.; Ohlendorf, D. H. Protein Sci. 1997, 6, 556-568.
46. Yoon, S.; Lippard, S. J. J. Am. Chem. Soc. 2004, 126, 2666-2667.
47. Kurtz, D. M., Jr. Chem. Rev. 1990, 90, 585-606.
48. Liu, T.; Lovell, T.; Han, W.-G.; Noodleman, L. Inorg. Chem. 2003, 42, 5244-5251.
49. Brown, I. D.; Altermatt, D. Acta Crystallogr. 1985, B41, 244-247.
50. Harlan, E. W.; Berg, J. M.; Holm, R. H. J. Am. Chem. Soc. 1986, 108, 6992-7000.
51. Rardin, R. L.; Tolman, W. B.; Lippard, S. J. New J. Chem. 1991, 15, 417-430.
52. CRC Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1979; Vol. 60.
53. Yoon, S.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 8386-8397.
54. Lee, D.; DuBois, J. L.; Pierce, B.; Hedman, B.; Hodgson, K. O.; Hendrich, M. P.; Lippard, S. J. Inorg. Chem. 2002, 41, 3172-3182.
55. Liu, K. E.; Valentine, A. M.; Wang, D.; Huynh, B. H.; Edmondson, D. E.; Salifoglou, A.; Lippard, S. J. J. Am. Chem. Soc. 1995, 117, 10174-10185.
56. Broadwater, J. A.; Ai, J.; Loehr, T. M.; Sanders-Loehr, J.; Fox, B. G. Biochemistry 1998, 37, 14664-14671.
57. Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876-3887.
58. Lee, S.-K.; Lipscomb, J. D. Biochemistry 1999, 38, 4423-4432.
59. Bollinger, J. M., Jr.; Tong, W. H.; Ravi, N.; Huynh, B. H.; Edmondson, D. E.; Stubbe, J. J. Am. Chem. Soc. 1994, 116, 8015-8023.
60. Mackle, H.; O'Hare, P. A. G. Tetrahedron 1963, 19, 961-971.
61. Douglas, T. B. J. Am. Chem. Soc. 1946, 68, 1072-1076.
62. Logan, D. T.; Su, X.-D.; Åberg, A.; Regnström, K.; Hajdu, J.; Eklund, H.; Nordlund, P. Structure 1996, 4, 1053-1064.
63. Rosenzweig, A. C.; Nordlund, P.; Takahara, P. M.; Frederick, C. A.; Lippard, S. J. Chem. Biol. 1995, 2, 409-418.
64. White, R. D.; Fox, B. G. Biochemistry 2003, 42, 7828-7835.
65. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329-2363.
66. Tshuva, E. Y.; Lee, D.; Bu, W.; Lippard, S. J. J. Am. Chem. Soc. 2002, 124, 2416-2417.
67. Moreira, R. F.; Tshuva, E. Y.; Lippard, S. J. Inorg. Chem. 2004, 43, 4427-4434.
68. Chen, C.-T.; Siegel, J. S. J. Am. Chem. Soc. 1994, 116, 5959-5960.
69. Fox, B. G.; Hendrich, M. P.; Surerus, K. K.; Andersson, K. K.; Froland, W. A.; Lipscomb, J. D.; Münck, E. J. Am. Chem. Soc. 1993, 115, 3688-3701.