Copper monooxygenase models. Aromatic hydroxylation by a dinuclear copper(I) complex containing methionine sulfur ligands

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 24, 1997, Pages 4789-4794

  Alzuet, Gloria ^a   Casella, Luigi ^a   Villa, Maria Laura ^a   Carugo, Oliviero ^a   Gullotti, Michele ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748826191     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705225a     Document Type: Article

References (82)

1. (a) K. D. Karlin and Z. Tyeklàr, Bioinorganic Chemistry of Copper, Chapman & Hall, New York, 1993;
2. (b) K. D. Karlin, Z. Tyeklàr and A. D. Zuberbühler in Bioinorganic Catalysis, ed. J. Reedijk, Marcel Dekker, New York, 1993, p. 261;
3. (c) K. D. Karlin, S. Kaderli and A. D. Zuberbühler, Acc. Chem. Res., 1997, 30, 139;
4. (d) W. B. Tolman, Acc. Chem. Res., 1997, 30, 327.
5. K. D. Karlin and Y. Gultneh, Prog. Inorg. Chem., 1987, 35, 219;
6. Z. Tyeklàr and K. D. Karlin, Acc. Chem. Res., 1989, 22, 241;
7. K. D. Karlin and Z. Tyeklàr, Adv. Inorg. Biochem., 1993, 9, 123;
8. T. N. Sorrell, Tetrahedron, 1989, 45, 3;
9. P. A. Vigato, S. Tamburini and D. E. Fenton, Coord. Chem. Rev., 1990, 106, 25.
10. N. Kitajima, Adv. Inorg. Chem., 1992, 39, 1;
11. N. Kitajima and Y. Moro-oka, Chem. Rev., 1994, 94, 737;
12. L. I. Simàndi in Catalytic Activation of Dioxygen by Metal Complexes, Kluwer, Dordrecht, 1992, ch. 5;
13. E. Spodine and J. Manzur, Coord. Chem. Rev., 1991, 119, 171;
14. T. N. Sorrell, W. E. Allen and P. S. White, Inorg. Chem., 1995, 34, 952;
15. S. Mahapatra, J. A. Halfen, E. C. Wilkinson, G. Pan, C. J. Cramer, L. Que, jun. and W. B. Tolman, J. Am. Chem. Soc., 1995, 117, 8865;
16. Y. Moro-oka, K. Fujisawa and N. Kitajima, Pure App. Chem., 1995, 67, 241;
17. J. A. Halfen, S. Mahapatra, E. C. Wilkinson, S. Kaderli, V. G. Young, jun., L. Que, jun., A. D. Zuberbühler and W. B. Tolman, Science, 1996, 271, 1397.
18. E. I. Solomon, M. J. Baldwin and M. D. Lowery, Chem. Rev., 1992, 92, 521;
19. E. I. Solomon in Copper Proteins, ed. T. G. Spiro, Wiley, New York, 1981, ch. 2;
20. K. Lerch, Life Chem. Rep., 1987, 5, 221;
21. D. A. Robb in Copper Proteins and Copper Enzymes, ed. R. Lontie, CRC Press, Boca Raton, FL, 1984, vol. 2, p. 207;
22. K. A. Magnus, H. Ton-That and J. E. Carpenter, Chem. Rev., 1994, 94, 727;
23. E. I. Solomon, U. M. Sundaramand T. E. Machonkin, Chem. Rev., 1996, 96, 2563.
24. R. R. Gagné, R. S. Gall, G. C. Lisensky, R. E. Marsh and L. M. Speltz, Inorg. Chem., 1979, 18, 771;
25. M. Réglier, E. Amadei, R. Tadayoni and B. Waegell, J. Chem. Soc., Chem. Commun., 1989, 447.
26. (a) K. D. Karlin, J. C. Hayes, Y. Gultneh, R. W. Cruse, J. W. McKown, J. P. Hutchinson and J. Zubieta, J. Am. Chem. Soc., 1984, 106, 2121;
27. (b) M. S. Nasir, K. D. Karlin, D. McGowty and J. Zubieta, J. Am. Chem. Soc., 1991, 113, 698;
28. (c) K. D. Karlin, M. S. Nasir, B. I. Cohen, R. W. Cruse, S. Kaderli and A. D. Zuberbühler, J. Am. Chem. Soc., 1994, 116, 1324.
29. (a) L. Casella, M. Gullotti, G. Pallanza and L. Rigoni, J. Am. Chem. Soc., 1988, 110, 4221;
30. (b) O. J. Gelling, A. Meetsma and B. L. Feringa, Inorg. Chem., 1990, 29, 2816;
31. (c) R. Menif, A. E. Martell, P. J. Squattrito and A. Clearfield, Inorg. Chem., 1990, 29, 4723;
32. (d) T. N. Sorrell and M. L. Garrity, Inorg. Chem., 1991, 30, 210;
33. (e) L. Casella, M. Gullotti, M. Bartosek, G. Pallanza and E. Laurenti, J. Chem. Soc., Chem. Commun., 1991, 1235.
34. (a) J. S. Thompson, J. Am. Chem. Soc., 1984, 106, 8308;
35. (b) M. G. Patch, V. McKee and C. A. Reed, Inorg. Chem., 1987, 26, 776;
36. (c) P. Capdevielle and M. Maumy, Tetrahedron Lett., 1991, 32, 3831;
37. (d) E. Amadéi, E. H. Alilou, F. Eydoux, M. Pierrot, M. Réglier and B. Waegell, J. Chem. Soc., Chem. Commun., 1992, 1782;
38. (e) A. E. Koziol, R. C. Palenik and G. J. Palenik, J. Chem. Soc., Chem. Commun., 1989, 650;
39. (f) K. V. Reddy, S.-J. Jin, P. K. Arora, D. S. Sfeir, S. C. F. Maloney, F. L. Urbach and L. M. Sayre, J. Am. Chem. Soc., 1990, 112, 2332;
40. (g) S. Itoh, T. Kondo, M. Komatsu, Y. Ohshiro, C. Li, N. Kanehisa, Y. Kai and S. Fukuzumi, J. Am. Chem. Soc., 1995, 117, 4714;
41. (h) S. Mahapatra, J. A. Halfen and W. B. Tolman, J. Am. Chem. Soc., 1996, 118, 11 575;
42. (i) J. A. Halfen, V. G. Young, jun. and W. B. Tolman, J. Am. Chem. Soc., 1996, 118, 10 920.
43. (a) L. C. Stewart and J. R Klinman, Annu. Rev. Biochem., 1988, 57, 551;
44. (b) M. C. Brenner and J. R Klinman, Biochemistry, 1989, 28, 4664;
45. (c) T. M. Pettingill, R. W. Strange and N. J. Blackburn, J. Biol. Chem., 1991, 266, 16 996;
46. (d) N. J. Blackburn, S. S. Hasnain, T. M. Pettingill and R. W. Strange, J. Biol. Chem., 1991, 266, 23 120;
47. (e) B. J. Reedy and N. J. Blackburn, J. Am. Chem. Soc., 1994, 116, 1924;
48. (f) B. J. Reedy, N. N. Murthy, K. D. Karlin and N. J. Blackburn, J. Am. Chem. Soc., 1995, 117, 9826.
49. (a) D. J. Merkler, R. Kulathila, S. D. Young, J. Freeman and J. J. Villafranca in ref. 1(a), p. 196;
50. (b) B. A. Eipper, A. S. W. Quon, R. E. Mains, J. S. Boswell and N. J. Blackburn, Biochemistry, 1995, 34, 2857;
51. (c) J. S. Boswell, B. J. Reedy, R. Kulathila, D. Merkler and N. J. Blackburn, Biochemistry, 1996, 35, 12 241.
52. L. Casella and M. Gullotti in ref. 1(a), p. 292.
53. R. A. Scott, R. J. Sullivan, W. E. De Wolf, jun., R. E. Dolle and L. I. Kruse, Biochemistry, 1988, 27, 5411.
54. L. Casella and J. A. Ibers, Inorg. Chem., 1981, 20, 2438;
55. D. E. Fogg and B. R. James, Inorg. Chem., 1995, 34, 2557.
56. S. K. Mandai and K. Nag, J. Chem. Soc., Chem. Commun., 1984, 2141.
57. D. E. Nikles, A. B. Anderson and F. L. Urbach in Copper Coordination Chemistry: Biochemical and Inorganic Perspectives, eds. K. D. Karlin and J. Zubieta, Adenine Press, New York, 1983, p. 203;
58. H. J. Schugar, Copper Coordination Chemistry: Biochemical and Inorganic Perspectives, ibid., p. 43;
59. J. V. Dagdigian, V. McKeeand C. A. Reed, Inorg. Chem., 1982, 21, 1332;
60. L. Casella, Inorg. Chem., 1984, 23, 2781.
61. (a) A. R. Amundsen, J. Whelan and B. Bosnien, J. Am. Chem. Soc., 1977, 99, 6730;
62. (b) A. Garnier-Suillerot, J.-P. Albertini, A. Collet, L. Faury, J.-M. Pastor and L. Tosi, J. Chem. Soc., Dalton Trans., 1981, 2544;
63. (c) T. Kiss and A. Gergely, J. Chem. Soc., Dalton Trans., 1984, 1951;
64. (d) L. Lorösch, W. Haase and P. Huong, J. Inorg. Biochem., 1986, 27, 53;
65. (e) R. C. Holz, J. M. Brink, F. T. Gobena and C. J. O'Connor, Inorg. Chem., 1994, 33, 6086.
66. L. Casella and M. Gullotti, J. Am. Chem. Soc., 1981, 103, 6338;
67. L. Casella, M. Gullotti and G. Pacchioni, J. Am. Chem. Soc., 1982, 104, 2386;
68. L. Casella and M. Gullotti, J. Am. Chem. Soc., 1983, 105, 803;
69. Inorg. Chem., 1986, 25, 1293;
70. L. Casella, M. Gullotti, A. Pintar, L. Messori, A. Rockenbauer and M. Györ, Inorg. Chem., 1987, 26, 1031.
71. S. S. Tandon, L. K. Thompson, J. N. Bridson, V. McKee and A. J. Downard, Inorg. Chem., 1992, 31, 4635.
72. M. Becker, S. Schindler and R. van Eldik, Inorg. Chem. 1994, 33, 5370.
73. K. D. Karlin, P. Ghosh, R. W. Cruse, A. Farooq, Y. Gultneh, R. R. Jacobson, N. J. Blackburn, R. W. Strange and J. Zubieta, J. Am. Chem. Soc., 1988, 110, 6769;
74. P. Ghosh, Z. Tyeklár, K. D. Karlin, R. R. Jacobson and J. Zubieta, J. Am. Chem. Soc., 1987, 109, 6889;
75. M. Mahroof-Tahir, N. N. Murthy, K. D. Karlin, N. J. Blackburn, S. N. Shaikh and J. Zubieta, Inorg. Chem., 1992, 31, 3001.
76. P. Hemmerich and C. Sigwart, Experientia, 1963, 19, 488.
77. (a) A. B. Frenz and Associated Inc., SDP Structure Determination Package, College Station, TX, Enraf-Nonius, Delft, 1985;
78. (b) MOLEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, 1990.
79. P. Main, S. J. Fiske, S. J. Hull, L. Lessinger, G. Germain, J. P. Declercq and M. M. Woolfson, MULTAN 80, A System of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data, Universities of York and Louvain, 1980.
80. W. H. Zachariesen, Acta Crystallogr., 1963, 16, 1139.
81. International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, 1974, vol. 4, pp. 99 and 149.
82. N. Walker and D. Stuart, Acta Crystallogr., Sect. A, 1983, 39, 159.