Less symmetrical dicopper(II) complexes as catechol oxidase models - An adjacent thioether group increases catecholase activity

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1201-1209

  Merkel, Michael ^a   Möller, Niclas ^a   Piacenza, Manuel ^a   Grimme, Stefan ^a   Rompel, Annette ^a   Krebs, Bernt ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Bioinorganic chemistry; Catechol oxidase; Copper; Enzyme models; Structure property relationships

Indexed keywords

COPPER; MIXTURES; NUCLEATION; PHENOLS; POSITIVE IONS; SPECTROSCOPY;

COPPER COMPLEXES; COPPER IONS; LIGANDS; PHENOLIC RING;

ENZYMES;

4 BROMO 2 (4 METHYLPIPERAZIN 1 YLMETHYL) 6 [[2 (1 PIPERIDYL)ETHYL]AMINOMETHYL]PHENOL; 4 BROMO 2 (4 METHYLPIPERAZIN 1 YLMETHYL) 6 [[2 (MORPHOLIN 4 YL)ETHYL]AMINOMETHYL]PHENOL; 4 BROMO 2 (4 METHYLPIPERAZIN 1 YLMETHYL) 6 [[2 (THIOMORPHOLIN 4 YL)ETHYL]AMINOMETHYL]PHENOL; CATECHOL OXIDASE; COPPER COMPLEX; DICOPPER COMPLEX; LIGAND; PHENOL DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BINDING SITE; COMPARTMENT MODEL; COMPLEX FORMATION; ENZYME ACTIVITY; ENZYME STRUCTURE; LIGAND BINDING; METAL BINDING; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

CATECHOL OXIDASE; COPPER; CRYSTALLOGRAPHY, X-RAY; ENZYME ACTIVATION; KINETICS; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MORPHOLINES; ORGANOMETALLIC COMPOUNDS; PHENOLS; PIPERIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES;

EID: 14544299586     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400768     Document Type: Article

References (69)

1. E. I. Solomon, U. M. Sundaram, T. E. Machonkin, Chem. Rev. 1996, 96, 2563.
2. J. Bonaventura, C. Bonaventura, Am. Zool. 1980, 20, 7.
3. T. T. Herskovitz, Comp. Biochem. Physiol. 1988, 91, 597.
4. H. S. Mason, Nature 1956, 177, 79.
5. F. Kubowitz, Biochem. Z. 1937, 292, 222.
6. F. Kubowitz, Biochem. Z. 1938, 299, 32.
7. A. M. Mayer, E. Harel, Phytochemistry 1979, 18, 193.
8. Y. M. Jiang, J. R. Fu, G. Zauberman, Y. Fuchs, J. Sci. Food Agric. 1999, 79, 950.
9. B. Paul, L. R. Gowda, J. Agric. Food Chem. 2000, 48, 3839.
10. C. P. Yang, S. Fujita, S. M. Ashrafuzzaman, N. Nakamura, N. Hayashi, J. Agric. Food Chem. 2000, 48, 2732.
11. F. Bilka, A. Balazova, A. Bilkova, M. Psenak, Pharmazie 2000, 55, 155.
12. P. Mazzafera, S. P. Robinson, Phytochemistry 2000, 55, 285.
13. A. Rompel, H. Fischer, D. Meiwes, K. Büldt-Karentzopoulos, R. Dillinger, F. Tuczek, H. Witzel, B. Krebs, J. Biol. Inorg. Chem. 1999, 4, 56.
14. T. Klabunde, C. Eicken, J. C. Sacchettini, B. Krebs, Nat. Struct. Biol. 1998, 5, 1084.
15. K. Lerch, J. Biol. Chem. 1982, 257, 6414.
16. C. Gielens, N. De Geest, X. Q. Xin, B. Devreese, J. Ban Beeumen, G. Preaux, Eur. J. Biochem. 1997, 248, 879.
17. M. E. Muff, K. I. Miller, K. E. van Holde, W. A. Hendrickson, J. Mol. Biol. 1998, 278, 855.
18. N. Ito, S. E. V. Phillips, K. D. S. Yadav, P. F. Knowles, J. Mol. Biol. 1994, 238, 794.
19. T. Kruse, T. Weyhermüller, K. Wieghardt, Inorg. Chim. Acta 2002, 331, 81.
20. L. M. Mirica, X. Ottenwaelder, T. D. P. Stack, Chem. Rev. 2004, 104, 1013.
21. E. A. Lewis, W. B. Tolman, Chem. Rev. 2004, 104, 1047.
22. K. D. Karlin, S. Kaderli, A. D. Zuberbühler, Acc. Chem. Res. 1997, 30, 139.
23. S. Fox, K. D. Karlin, Active Oxygen in Biochemistry (Eds.: J. S. Valentine, C. S. Foote, A. Greenberg, J. F. Liebman), Chapman & Hall, Glasgow, 1995, p. 188.
24. N. Kitajima, W. B. Tolman, Prog. Inorg. Chem. 1995, 43, 419.
25. W. B. Tolman, Acc. Chem. Res. 1997, 30, 227.
26. E. I. Solomon, F. Tuczek, D. E. Root, C. A. Brown, Chem. Rev. 1994, 94, 827.
27. N. Kitajima, Y. Moro-oka, Chem. Rev. 1994, 94, 737.
28. K. D. Karlin, Z. Tyeklár, Adv. Inorg. Biochem. 1994, 9, 123.
29. N. Kitajima, Y. Moro-oka, J. Chem. Soc. Dalton Trans. 1993, 2665.
30. T. N. Sorrell, Tetrahedron 1989, 45, 3.
31. Z. Tyeklár, K. D. Karlin, Acc. Chem. Res. 1989, 22, 241.
32. K. D. Karlin, Y. Gultneh, Prog. Inorg. Chem. 1987, 35, 219.
33. C. Belle, J.-L. Pierre, Eur. J. Inorg. Chem. 2003, 4137.
34. S. Torelli, C. Belle, S. Hamman, J.-L. Pierre, Inorg. Chem. 2002, 41, 3983.
35. C. Eicken, B. Krebs, J. C. Sacchettini, Curr. Opin. Struct. Biol. 1999, 9, 677.
36. K. D. Karlin, Y. Gultneh, T. Nicholson, J. Zubieta, Inorg. Chem. 1985, 24, 3727.
37. J. Ackermann, F. Meyer, E. Kaifer, H. Pritzkow, Chem. Eur. J. 2002, 8, 247.
38. I. A. Koval, M. Huisman, A. F. Stassen, P. Gamez, M. Lutz, A. L. Spek, J. Reedijk, Eur. J. Inorg. Chem. 2004, 591.
39. I. A. Koval, D. Pursche, A. F. Stassen, P. Gamez, B. Krebs, J. Reedijk, Eur. J. Inorg. Chem. 2003, 1669.
40. N. Möller, M. Lüken, B. Krebs, J. Inorg. Biochem. 2001, 86, 344.
41. M. S. Nasir, K. D. Karlin, D. McGowty, J. Zubieta, J. Am. Chem. Soc. 1991, 113, 698.
42. J. Reim, B. Krebs, J. Chem. Soc. Dalton Trans. 1997, 3893.
43. N. N. Murthy, M. Mahroof-Tahir, K. D. Karlin, Inorg. Chem. 2001, 40, 628.
44. C. Fernandes, A. Neves, A. J. Bortoluzzi, A. S. Mangrich, E. Rentschler, B. Szpoganicz, E. Schwingel, Inorg. Chim. Acta 2001, 320, 12.
45. C. Eicken, F. Zippel, K. Büldt-Karentzopoulos, B. Krebs, FEBS Lett. 1998, 436, 293.
46. H. Adams, G. Candeland, J. D. Crane, D. E. Fenton, A. J. Smith, J. Chem. Soc. Chem. Commun. 1990, 93.
47. J. D. Crane, D. E. Fenton, J.-M. Latour, A. J. Smith, J. Chem. Soc. Dalton Trans. 1991, 2979.
48. L. D. Wise, G. C. Morrison, K. Egan, M. A. Commarato, G. Kopia, E. C. Lattime, J. Med. Chem. 1974, 17, 1232.
49. G. M. Sheldrick, SHELX-97, Universität Göttingen, 1997.
50. CCDC-244275, CCDC-244276, and CCDC-244277 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk).
51. R. Ahlrichs, M. Bär, H.-P. Baron, R. Bauernschmitt, S. Böcker, M. Ehring, K. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Häser, H. Horn, C. Huber, U. Huniar, M. Kattannek, C. Kölmel, M. Kollwitz, K. May, C. Ochsenfeld, H. Öhm, A. Schäfer, U. Schneider, O. Treutier, M. von Arnim, F. Weigend, P. Weis, H. Weiss, TURBOMOLE (Version 5.3), Universität Karlsruhe, 2000.
52. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
53. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
54. F. Weigend, M. Häser, Theor. Chem. Acc. 1997, 97, 331.
55. The basis sets are available from the TURBOMOLE homepage (http://www.turbomole.com) through the FTP Server button (in the subdirectories basen, jbasen, and cbasen).
56. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571.
57. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829.
58. A. W. Addison, A. N. Rao, J. Reedjik, J. Rijn, G. C. Verschoor, J. Chem. Soc. Dalton Trans. 1984, 1349; definition of τ: τ = (largest bond angle - second largest bond angle)/60, that is τ = 1 for trigonal bipyramidal, τ = 0 for square pyramidal.
59. E. I. Solomon, K. W. Penfield, D. E. Wilcox, Struct. Bonding (Berlin) 1983, 53, 1.
60. P. K. Coughlin, S. J. Lippard, J. Am. Chem. Soc. 1981, 103, 3228.
61. K. D. Karlin, A. Farooq, J. C. Hayes, B. I. Cohen, T. M. Rowe, E. Sinn, J. Zubieta, Inorg. Chem. 1987, 26, 1271.
62. Y. Nakao, Y. Oohata, Y. Fujiwara, M. Itadani, T. Sakurai, A. Ichimura, W. Mori, Bull. Chem. Soc. Jpn. 1993, 66, 2112.
63. K. D. Karlin, I. Sanyal, A. Farooq, R. R. Jacobson, S. N. Shaikh, J. Zubieta, Inorg. Chim. Acta 1990, 174, 13.
64. E. W. Ainscough, A. G. Bingham, A. M. Brodie, J. M. Husbands, J. E. Plowman, J. Chem. Soc. Dalton Trans. 1981, 1701.
65. K. Bertoncello, G. D. Fallon, J. H. Hodgkin, K. S. Murray, Inorg. Chem. 1988, 27, 4750.
66. B. J. Hathaway, J. Chem. Soc. Dalton Trans. 1972, 1196.
67. B. J. Hathaway in Comprehensive Coordination Chemistry, Vol. 5 (Ed.: G. Wilkinson), Pergamon, New York, 1987, 553.
68. A. L. Capparelli, J. Marañon, O. M. Sobarrain, R. R. Filgueira, J. Mol. Struct. 1974, 23, 145.
69. M. Ladika, N. G. Rondan, J. Mol. Struct. 1996, 365, 21.