Dinuclear nickel(II) complexes as models for the active site of urease

Inorganic Chemistry

Volumn 35, Issue 13, 1996, Pages 3792-3803

  Volkmer, Dirk ^a   Hommerich, Birgit ^a   Griesar, Klaus ^b   Haase, Wolfgang ^b   Krebs, Bernt ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001542285     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic951567x     Document Type: Article

References (89)

1. For comprehensive reviews see: (a) Blakeley, R. L.; Zerner, B J. Mol. Catal. 1984, 23, 263. (b) Andrews, R. K.; Blakeley, R. L.; Zerner, B. Met. Ions Biol. Syst. 1988, 23, 186 (c) Mobley, H L. T.; Hausinger, R P. Microbiol. Rev. 1989, 53, 85. (d) Kolodziej, A. F. Prog. Inorg. Chem. 1994, 41, 493.
2. For comprehensive reviews see: (a) Blakeley, R. L.; Zerner, B J. Mol. Catal. 1984, 23, 263. (b) Andrews, R. K.; Blakeley, R. L.; Zerner, B. Met. Ions Biol. Syst. 1988, 23, 186 (c) Mobley, H L. T.; Hausinger, R P. Microbiol. Rev. 1989, 53, 85. (d) Kolodziej, A. F. Prog. Inorg. Chem. 1994, 41, 493.
3. For comprehensive reviews see: (a) Blakeley, R. L.; Zerner, B J. Mol. Catal. 1984, 23, 263. (b) Andrews, R. K.; Blakeley, R. L.; Zerner, B. Met. Ions Biol. Syst. 1988, 23, 186 (c) Mobley, H L. T.; Hausinger, R P. Microbiol. Rev. 1989, 53, 85. (d) Kolodziej, A. F. Prog. Inorg. Chem. 1994, 41, 493.
4. For comprehensive reviews see: (a) Blakeley, R. L.; Zerner, B J. Mol. Catal. 1984, 23, 263. (b) Andrews, R. K.; Blakeley, R. L.; Zerner, B. Met. Ions Biol. Syst. 1988, 23, 186 (c) Mobley, H L. T.; Hausinger, R P. Microbiol. Rev. 1989, 53, 85. (d) Kolodziej, A. F. Prog. Inorg. Chem. 1994, 41, 493.
5. Sumner, J. B. J. Biol. Chem. 1926, 69, 435.
6. (a) Dixon, N E.; Gazzola, C.; Watters, J. J.; Blakeley, R. L.; Zerner, B. J. Am. Chem. Soc. 1975, 97, 4130.
7. (b) Dixon, N. E.; Gazzola, C.; Blakeley, R. L.; Zerner, B. J. Am. Chem. Soc. 1975, 97, 4131.
8. (a) Todd, M. J.; Hausinger, R. P. J. Biol. Chem. 1987, 262, 5963.
9. (b) Breitenbach, J. M.; Hausinger, R. P Biochem. J. 1988, 250, 917.
10. (c) Jones, B. D.; Mobley, H. L. T. J. Bacteriol. 1988, 170, 3342.
11. (d) Hu, L.-T.; Mobley, H. L. T. Infect. Immun. 1990, 58, 992.
12. Sriwanthana, B.; Mobley, H L. T. Infect. Immun. 1993, 61, 2570.
13. Dixon, N. E.; Riddles, P. W.; Gazzola, C.; Blakeley, R. L.; Zerner, B. Can. J. Biochem. 1980, 58, 1335; Erratum. Ibid. 1981, 59, 564.
14. Jabri, E.; Carr, M. B.; Hausinger, R. P., Karplus, P. A Science 1995, 268, 998.
15. (a) Wang, S.; Lee, M. H.; Hausinger, R. P.; Clark, P. A.; Wilcox, D. E.; Scott, R. A. Inorg. Chem. 1994, 33, 1589.
16. (b) Day, E. P.; Peterson, J.; Sendova, M. S.; Todd, M. J.; Hausinger, R. P. Inorg. Chem. 1993, 32, 634.
17. (c) Clark, P. A.; Wilcox, D. E. Inorg. Chem. 1989, 28, 1326.
18. (d) Clark, P. A.; Wilcox, D. E.; Scott, R. A. Inorg. Chem. 1990, 29, 579.
19. (e) Blakeley, R. L.; Dixon, N. E.; Zerner, B. Biochim. Biophys. Acta 1983, 744, 219.
20. (f) Alagna, L., Hasnam, S. S.; Piggott, B.; Williams, D. J. Biochem. J. 1984, 220, 591.
21. Volkmer, D.; Horstmann, A.; Griesar, K.; Haase, W.; Krebs, B. Inorg. Chem. 1996, 35, 1132.
22. Suzuki, M.; Kanatomi, H., Murase, I. Bull. Chem. Soc. Jpn. 1984, 57, 36.
23. McKee, V.; Zvagulis, M.; Dagdigian, J. V.; Patch, M. G., Reed, C. A. J. Am. Chem. Soc. 1984, 106, 4765.
24. Grandberg, I. I.; Sharova, G. I. Khim. Geterosikl. Soedin 1968, 2, 325; Chem. Abstr. 1968, 69, 96564k.
25. Grandberg, I. I.; Sharova, G. I. Khim. Geterosikl. Soedin 1968, 2, 325; Chem. Abstr. 1968, 69, 96564k.
26. International Tables for X-Ray Crystallography, Kynoch Press: Birmingham, U.K., 1974; Vol. 4.
27. (a) Todd, M. J., Hausinger, R. P. J. Biol. Chem. 1989, 264, 15835.
28. (b) Unmack, A. Z. Phys. Chem. 1928, 133, 45.
29. -1.
30. Wilkins, R. G. Kinetics and Mechanism of Reactions of Transition Metal Complexes: 2nd, thoroughly revised ed.; VCH:Weinheim. Germany, 1991; Chapters 1.2.1 and 3.
31. m(cat)).
32. (a) Uhlenbrock, S.; Krebs, B. Angew. Chem. 1992, 104, 1631; Angew. Chem., Int. Ed. Engl. 1992, 31, 1647.
33. (a) Uhlenbrock, S.; Krebs, B. Angew. Chem. 1992, 104, 1631; Angew. Chem., Int. Ed. Engl. 1992, 31, 1647.
34. (b) Wall, M.; Hynes, R. C., Chin, J. Angew. Chem. 1993, 105, 1696; Angew. Chem., Int. Ed. Engl. 1993, 32, 1633.
35. (b) Wall, M.; Hynes, R. C., Chin, J. Angew. Chem. 1993, 105, 1696; Angew. Chem., Int. Ed. Engl. 1993, 32, 1633.
36. (c) Berends, H. P.; Stephan, D. W. Inorg. Chim. Acta 1985, 99, L53.
37. (d) Berends, H. P.; Stephan, D. W. Inorg. Chem. 1987, 26, 749.
38. (e) Patch, M. G.; Hok-kin Choi; Chapman, D. R.; Bau, R.; McKee, V.; Reed, C. A. Inorg. Chem. 1990, 29, 110.
39. (a) Pessiki, P. J.; Khangulov, S. V.; Ho, D. M.; Dismukes, G. C. J. Am. Chem. Soc. 1994, 116, 891.
40. (b) Bremer, B.; Schepers, K.; Fleischhauer, P.; Haase, W.; Henkel, G.; Krebs B. J. Chem. Soc., Chem. Commun. 1991, 510.
41. (c) Ménage, S.: Brennan, B. A.: Juarez-Garcia, C.; Munck, E.: Que, L., Jr. J. Am. Chem. Soc. 1990, 112, 6423.
42. (d) Yanhong Dong; Ménage, S.: Brennan, B. A.; Elgren, T. E.; Jang, Ho G., Pearce, L. L.; Que, L, Jr. J. Am. Chem. Soc. 1993, 115, 1851.
43. (e) Brennan, B. A.; Qiuhao Chen; Juarez-Garcia, C.; True, A. E.: O'Connor, C. J.; Que, L., Jr Inorg. Chem. 1991, 30, 1937.
44. (f) Qiuhao Chen; Lynch. J. B.; Gomez-Romero, P.; Ben-Hussein, A.; Jameson, G. B.; O'Connor, C. J.; Que, L, Jr. Inorg. Chem. 1988, 27, 2673.
45. (g) McKee, V.; Dagdigian, J. V.; Bau, R.; Reed, C A. J. Am. Chem. Soc. 1981, 103, 7000.
46. (h) McKee, V.; Zvagulis, M.; Reed, C. A. Inorg. Chem. 1985, 24, 2914.
47. (a) Satcher, J. H.; Droege, M. W.; Weakley, T. J. R.; Taylor, R. T. Inorg. Chem. 1995, 34, 3317.
48. (b) Droege, M. W.; Satcher, J. H., Jr.; Reibold, R. A., Weakley, T. J. R.; Chauffe, L.; Watkins, B. E. Prepr. Pap. Am. Chem. Soc., Div Fuel Chem. 1992, 37, 1534
49. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
50. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
51. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
52. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
53. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
54. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
55. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
56. -, LH = N-phenylsalicylaldimine, Ni⋯Ni = 3.10 Å, φ = 106.6°. (h) Butcher, R. J., O'Connor, C J.; Sinn, E. Inorg. Chem. 1982, 21, 661.
57. Since compound 4 was the only example for type 3 that we were actually aware of. we did not think it right to assign typical values for that structure type.
58. O'Connor, C. D. Prog. Inorg. Chem. 1982, 29, 239
59. 2/3 kT) (2kT/D) + 2 exp(-D/kT)/(D/kT) + exp(-D/kt)/ 1 + 2 exp(-D/kT)
60. Turpeinen, U.; Hämälämen, R.; Reedijk, J. Polyhedron 1987, 6, 1603.
61. For magnetic susceptibility measurements the compounds were powdered and dried under high vacuum in order to remove the solvent molecules which are included in the crystal lattice. We cannot rule out the possibility of changes in the coordination of the Ni(II) ions due to the treatment of the samples, e.g. the terminally coordinated oxygen donors O(6) in the structures of 2 and 3 may become bridging ligands or dissociate off
62. Gorun, S. M.; Lippard, S. J. Inorg. Chem, 1991, 30, 1625.
63. Underbill, A. E., Billing, D. E. Nature 1966, 210, 834.
64. (a) Ciampolini, M. Inorg. Chem. 1966, 5, 35.
65. (b) Sacconi, L.; Ciampolini, M.; Speroni, G. P. J. Am. Chem. Soc. 1965, 87, 3102.
66. (c) Ciampolini, M.; Nardi, N. Inorg. Chem. 1966, 5, 41.
67. 2g. 1300 nm. Magnetic circular dichroism study: Finnegan, M. G . Kowal, A. T.; Werth, M. T.; Clark, P. A.; Wilcox, D. F.; Johnson, M. K. J. Am Chem. Soc. 1991, 113, 4030.
68. 2g. 1300 nm. Magnetic circular dichroism study: Finnegan, M. G . Kowal, A. T.; Werth, M. T.; Clark, P. A.; Wilcox, D. F.; Johnson, M. K. J. Am Chem. Soc. 1991, 113, 4030.
69. The primary structure of the ureases from P. mirabilis, H. pylori, K. aerogenes, and jack beans have a common conservative sequence of 20 amino acid residues. Among those three histidine residues are found that are expected to be directly coordinated to the metal ions; cf. ref 5
70. 14a (c) Nonbuffered solutions of the complexes in MeOH, titrations with sodium 2-hydroxyethanethiolate, absorption coefficient related to the stoichiometric ratio of the complex/2-hydroxyethanethiolate of 1:1.
71. (a) Gould, R. O.; Harding. M. M. J. Chem. Soc. A 1970, 875.
72. -1), Krüger, T. Ph.D. Thesis, Münster. 1990.
73. The detection of mononuclear complexes of the ligands tbpOH, m-tbpOH, and bpepOH could not be proven by the electronic absorption spectra, which are dominated by the intense CT transitions of the cyclic polymers. Our experiences with complex formation with this kind of ligand show that mononuclear complexes are formed preferentially if no bridging anions are present that stabilize the dinuclear unit (vide infra).
74. (a) Chin, J. Acc. Chem. Res. 1991, 24, 145.
75. (b) Breslow, R. Acc. Chem. Res. 1995, 28, 146.
76. (a) De Rosch, M. A., Trogler, W. C. Inorg. Chem. 1990, 29, 2409.
77. (b) Koike, T., Kimura, E. J. Am. Chem. Soc. 1991, 113, 8935.
78. (c) Vance, D. H., Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165.
79. (d) Akkaya, E. U.; Czarnik, A W. J. Phys. Org. Chem. 1992, 5, 1992.
80. The use of substrates that contain activated leaving groups has been criticized repeatedly. However, the broad use of the mentioned test substrates allows us to compare the hydrolysis efficiency of different model systems and thus has set its own standard, (a) Menger, F. M: Ladika. M. J. Am. Chem. Soc. 1987, 109, 3145. (b) Breslow, R.; Singh, S. Bioorg. Chem. 1988, 16, 408.
81. The use of substrates that contain activated leaving groups has been criticized repeatedly. However, the broad use of the mentioned test substrates allows us to compare the hydrolysis efficiency of different model systems and thus has set its own standard, (a) Menger, F. M: Ladika. M. J. Am. Chem. Soc. 1987, 109, 3145. (b) Breslow, R.; Singh, S. Bioorg. Chem. 1988, 16, 408.
82. -1), which is presumably due to the coordination of the phenolate to one of the Ni(II) ions (vide infra).
83. (a) Mauser, H. Z. Naturforsch. 1968, 23B, 1025.
84. (b) Lachmann, H.; Mauser, H , Schneider, F.; Wenck, H. Z. Naturforsch. 1971, 26B, 629.
85. 5 at pH 14. Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3209.
86. Beringer, F. M.; Findler, E. M. J. Am. Chem. Soc. 1955, 77, 3200
87. (a) Wahnon, D.; Lebuis, A.-M; Chin, J. Angew. Chem. 1995, 107, 2594: Angew: Chem., Int Ed Engl 1995, 34, 2412.
88. (a) Wahnon, D.; Lebuis, A.-M; Chin, J. Angew. Chem. 1995, 107, 2594: Angew: Chem., Int Ed Engl 1995, 34, 2412.
89. (b) Chin. J.; Banaszczyk, M. J. Am. Chem Soc. 1989, 111, 4103