Solution and structural characterization of iron(II) complexes with ortho -halogenated phenolates: Insights into potential substrate binding modes in hydroquinone dioxygenases

Inorganic Chemistry

Volumn 49, Issue 23, 2010, Pages 10914-10929

  Rocks, Sara S ^a   Brennessel, William W ^a   MacHonkin, Timothy E ^b   Holland, Patrick L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

^b WHITMAN COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FERROUS ION; HYDROQUINONE DEHYDROGENASES; HYDROQUINONE DERIVATIVE; OXIDOREDUCTASE; PHENOL DERIVATIVE;

ARTICLE; BACTERIUM; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; HALOGENATION; X RAY CRYSTALLOGRAPHY;

BACTERIA; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; FERROUS COMPOUNDS; HALOGENATION; HYDROQUINONES; MODELS, MOLECULAR; OXIDOREDUCTASES; PHENOLS; SUBSTRATE SPECIFICITY;

EID: 78650237290     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101377u     Document Type: Article

References (83)

1. Toxicological Profile for Pentachlorophenol; PB/2001/109106/AS; U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry: Atlanta, GA, 2001.
2. Reregistration Eligibility Decision for Pentachlorophenol; EPA 739-R-08-008; U.S. Environmental Protection Agency, Office of Pesticide Programs: Arlington, VA, 2008.
3. Haggblom, M. M. FEMS Microbiol. Rev. 1992, 103, 29-72
4. Saber, D. L. and Crawford, R. L. Appl. Environ. Microbiol. 1985, 50, 1512-1518
5. Ederer, M. M., Crawford, R. L., Herwig, R. P., and Orser, C. S. Mol. Ecol. 1997, 6, 39-49
6. Nohynek, L. J., Suhonen, E. L., Nurmiaho-Lassila, E. L., Hantula, J., and Salkinoja-Salonen, M. Syst. Appl. Microbiol. 1996, 18, 527-538
7. Cai, M. and Xun, L. Y. J. Bacteriol. 2002, 184, 4672-4680
8. Dai, M. H. and Copley, S. D. Appl. Environ. Microbiol. 2004, 70, 2391-2397
9. Xu, L., Resing, K., Lawson, S. L., Babbitt, P. C., and Copley, S. D. Biochemistry 1999, 38, 7659-7669
10. Ohtsubo, Y., Miyauchi, K., Kanda, K., Hatta, T., Kiyohara, H., Senda, T., Nagata, Y., Mitsui, Y., and Takagi, M. FEBS Lett. 1999, 459, 395-398
11. Xun, L., Bohuslavek, J., and Cai, M. Biochem. Biophys. Res. Commun. 1999, 266, 322-325
12. Endo, R., Kamakura, M., Miyauchi, K., Fukuda, M., Ohtsubo, Y., Tsuda, M., and Nagata, Y. J. Bacteriol. 2005, 187, 847-853
13. Miyauchi, K., Adachi, Y., Nagata, Y., and Takagi, M. J. Bacteriol. 1999, 181, 6712-6719
14. Nagata, Y., Endo, R., Ito, M., Ohtsubo, Y., and Tsuda, M. Appl. Microbiol. Biotechnol. 2007, 76, 741-752
15. Bugg, T. D. H. and Winfield, C. J. Nat. Prod. Rep. 1998, 513-530
16. Solomon, E. I., Brunold, T. C., Davis, M. I., Kemsley, J. N., Lee, S.-K., Lehnert, N., Neese, F., Skulan, A. J., Yang, Y.-S., and Zhou, J. Chem. Rev. 2000, 100, 235-349
17. Bugg, T. D. H. and Lin, G. Chem. Commun. 2001, 941-952
18. Vaillancourt, F. H., Bolin, J. T., and Eltis, L. Ring-Cleavage Dioxygenases. In Pseudomonas; Ramos, J.-L., Ed.; Kluwer Academic/Plenum: New York, 2004; Vol. 3, pp 359 - 396.
19. Vaillancourt, F. H., Bolin, J. T., and Eltis, L. D. Crit. Rev. Biochem. Mol. Biol. 2006, 41, 241-267
20. Bugg, T. D. H. and Ramaswamy, S. Curr. Opin. Chem. Biol. 2008, 12, 134-140
21. Machonkin, T. E., Holland, P. L., Smith, K. N., Liberman, J. S., Dinescu, A., Cundari, T. R., and Rocks, S. S. J. Biol. Inorg. Chem. 2010, 10, 291-301
22. Klecka, G. M. and Gibson, D. T. Appl. Environ. Microbiol. 1981, 41, 1159-1165
23. Bartels, I., Knackmuss, H.-J., and Reineke, W. Appl. Environ. Microbiol. 1984, 47, 500-505
24. Cerdan, P., Wasserfallen, A., Rekik, M., Timmis, K. N., and Harayama, S. J. Bacteriol. 1994, 176, 6074-6081
25. Vaillancourt, F. H., Labbé, G., Drouin, N. M., Fortin, P. D., and Eltis, L. D. J. Biol. Chem. 2002, 277, 2019-2027
26. Dai, S., Vaillancourt, F. H., Maaroufi, H., Drouin, N. M., Neau, D. B., Snieckus, V., Bolin, J. T., and Eltis, L. D. Nat. Struct. Biol. 2002, 9, 934-939
27. Costas, M., Mehn, M. P., Jensen, M. P., and Que, L. Chem. Rev. 2004, 104, 939-986
28. Rheingold, A. L. and Miller, J. Private Communication to Cambridge Structural Database, 2003.
29. Heistand, R. H., Roe, A. L., and Que, L. Inorg. Chem. 1982, 21, 676-681
30. Maroney, M. J., Day, R. O., Psyris, T., Fleury, L. M., and Whitehead, J. P. Inorg. Chem. 1989, 28, 173-175
31. Doerner, A. E. and Machonkin, T. E. unpublished work.
32. Cambridge Structural Database, v. 5.31 (November 2009 update): Allen, F. H. Acta Crystallogr. 2002, B58, 380-388
33. Boxwell, C. J., Bhalla, R., Cronin, L., Turner, S. S., and Walton, P. H. J. Chem. Soc., Dalton Trans. 1998, 2449-2450
34. Cronin, L., Foxon, S. P., Lusby, P. J., and Walton, P. H. J. Biol. Inorg. Chem. 2001, 6, 367-377
35. Nairn, A. K., Bhalla, R., Foxon, S. P., Liu, X. M., Yellowlees, L. J., Gilbert, B. C., and Walton, P. H. J. Chem. Soc., Dalton Trans. 2002, 1253-1255
36. Archibald, S. J., Foxon, S. P., Freeman, J. D., Hobson, J. E., Perutz, R. N., and Walton, P. H. J. Chem. Soc., Dalton Trans. 2002, 2797-2799
37. Greener, B., Cronin, L., Wilson, G. D., and Walton, P. H. J. Chem. Soc., Dalton Trans. 1996, 401-403
38. Greener, B., Moore, M. H., and Walton, P. H. Chem. Commun. 1996, 27-28
39. Cronin, L., Greener, B., Foxon, S. P., Heath, S. L., and Walton, P. H. Inorg. Chem. 1997, 36, 2594-2600
40. Further details: Rocks, S. S. Ph.D. Thesis, University of Rochester, Rochester, New York, 2009.
41. Cushion, M., Ebrahimpour, P., Haddow, M. F., Hallett, A. J., Mansell, S. M., Orpen, A. G., and Wass, D. F. Dalton Trans. 2009, 1632-1635
42. 2 and phenolate without a supporting ligand. Additional spectra are shown in the Supporting Information.
43. Torzilli, M. A., Colquhoun, S., Kim, J., and Beer, R. H. Polyhedron 2002, 21, 705-713
44. Weber, B. and Walker, F. A. Inorg. Chem. 2007, 46, 6794-6803
45. Bertini, I., Luchinat, C., and Parigi, G. Solution NMR of Paramagnetic Molecules; Elsevier: Amsterdam, 2001.
46. Topspin, 1.3; Bruker: Rheinstetten, Germany, 2005.
47. Bollinger, J. E., Mague, J. T., Oconnor, C. J., Banks, W. A., and Roundhill, D. M. J. Chem. Soc., Dalton Trans. 1995, 1677-1688
48. Bollinger, J. E., Mague, J. T., and Roundhill, D. M. Inorg. Chem. 1994, 33, 1241-1242
49. Yang, J. Y., Shores, M. P., Sokol, J. J., and Long, J. R. Inorg. Chem. 2003, 42, 1403-1419
50. There are more than 100 crystallographically characterized iron(II) complexes with tethered phenolates as part of supporting multidentate ligands, primarily derived from salen. Selected examples: Jameson, G. B., March, F. C., Robinson, W. T., and Koon, S. S. J. Chem. Soc., Dalton Trans. 1978, 185-191
51. Cini, R. Inorg. Chim. Acta 1983, 73, 146-152
52. Kayal, A. and Lee, S. C. Inorg. Chem. 2002, 41, 321-330; see also ref 21
53. Ainscough, E. W., Addison, A. W., Dolphin, D., and James, B. R. J. Am. Chem. Soc. 1978, 100, 7585-7591
54. Phillippi, M. A., Shimomura, E. T., and Goff, H. M. Inorg. Chem. 1981, 20, 1322-1325
55. Weigel, J. A. and Holm, R. H. J. Am. Chem. Soc. 1991, 113, 4184-4191
56. Bartlett, R. A., Ellison, J. J., Power, P. P., and Shoner, S. C. Inorg. Chem. 1991, 30, 2888-2894
57. Ito, M., Amagai, H., Fukui, H., Kitajima, N., and Moro-oka, Y. Bull. Chem. Soc. Jpn. 1996, 69, 1937-1945
58. Pavel, E. G., Kitajima, N., and Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 3949-3962
59. Richard, M. J., Shaffer, C. D., and Evilia, R. F. Electrochim. Acta 1982, 27, 979-983
60. Arasasingham, R. D., Balch, A. L., Hart, R. L., and Latosgrazynski, L. J. Am. Chem. Soc. 1990, 112, 7566-7571
61. Johnston, D. H. and Shriver, D. F. Inorg. Chem. 1993, 32, 1045-1047
62. Hunter, C. A. and Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534
63. A review of different viewpoints may be found in: Wheeler, S. E., McNeil, A. J., Müller, P., Swager, T. M., and Houk, K. N. J. Am. Chem. Soc. 2010, 132, 3304-3311
64. There are two crystallographically characterized iron(III) phenolate compounds with 2,6-chloro substituents. Koch, S. A. and Millar, M. J. Am. Chem. Soc. 1982, 104, 5255-5257
65. Helms, A. M., Jones, W. D., and McLendon, G. L. J. Coord. Chem. 1991, 23, 351-359
66. Examples: Meyer, R., Gagliardi, J., and Wulfsberg, G. J. Mol. Struct. 1983, 111, 311-316
67. Wulfsberg, G., Yanisch, J., Meyer, R., Bowers, J., and Essig, M. Inorg. Chem. 1984, 23, 715-719
68. Colsman, M. R., Newbound, T. D., Marshall, L. J., Noirot, M. D., Miller, M. M., Wulfsberg, G. P., Frye, J. S., Anderson, O. P., and Strauss, S. H. J. Am. Chem. Soc. 1990, 112, 2349-2362
69. Kulawiec, R. J. and Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89-115
70. Garcia, M. P., Jimenez, M. V., Cuesta, A., Siurana, C., Oro, L. A., Lahoz, F. J., Lopez, J. A., Catalan, M. P., Tiripicchio, A., and Lanfranchi, M. Organometallics 1997, 16, 1026-1036
71. Poignant, G., Nlate, S., Guerchais, V., Edwards, A. J., and Raithby, P. R. Organometallics 1997, 16, 124-132
72. Wulfsberg, G., Parks, K. D., Rutherford, R., Jackson, D. J., Jones, F. E., Derrick, D., Ilsley, W., Strauss, S. H., Miller, S. M., Anderson, O. P., Babushkina, T. A., Gushchin, S. I., Kravchenko, E. A., and Morgunov, V. G. Inorg. Chem. 2002, 41, 2032-2040
73. Richardson, M. F., Wulfsberg, G., Marlow, R., Zaghonni, S., McCorkle, D., Shadid, K., Gagliardi, J., and Farris, B. Inorg. Chem. 1993, 32, 1913-1919
74. Our values come from a search of terminal Fe-halide complexes with four-coordinate iron, from structures without disorder, with R < 10%, in the Cambridge Crystallographic Database (November 2009). Similar numbers are quoted in the literature: Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G., and Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1-S83
75. Camurlu, P., Yilmaz, A., Tatar, L., Kisakürek, D., and Ülkü, D. Cryst. Res. Technol. 2005, 40, 271-276
76. Addison, A. W., Rao, T. N., Reedijk, J., Vanrijn, J., and Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356
77. Erikson, T. K. G., Bryan, J. C., and Mayer, J. M. Organometallics 1988, 7, 1930-1938
78. Holland, P. L. Comments Inorg. Chem. 1999, 21, 115-129
79. Hagadorn, J. R., Que, L., and Tolman, W. B. Inorg. Chem. 2000, 39, 6086-6090
80. Sheldrick, G. M. SADABS, version 2008/1; University of Göttingen: Göttingen, Germany, 2008.
81. SAINT, version 7.60A; Bruker AXS: Madison, WI, 2008.
82. Altomare, A., Burla, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., and Spagna, R. SIR97: A new program for solving and refining crystal structures; Istituto di Cristallografia, CNR: Bari, Italy, 1999.
83. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388