Functional mimics of copper enzymes. Synthesis and stereochemical properties of the copper(II) complexes of a trinucleating ligand derived from L-histidine

Tetrahedron Asymmetry

Volumn 10, Issue 2, 1999, Pages 281-295

  Santagostini, Laura ^a   Gullotti, Michele ^a   Pagliarin, Roberto ^a   Bianchi, Emanuela ^a   Casella, Luigi ^b   Monzani, Enrico ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 1H IMIDAZOLE 2 CARBALDEHYDE; COPPER II COMPLEX; N METHYLHISTIDINE; PIPERAZINE 1,4 BIS[4 (4 OXO 4 BUTANOIC ACID]; PIPERAZINE 1,4 BIS[4 (N(1 ACETOXY 3 (1 METHYL 1H IMIDAZOL 4 YL)) 2 PROPYL) N (1 METHYL 1H IMIDAZOL 2 YLMETHYL) AMINOBUTYL]COPPER COMPLEX; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; BINDING SITE; CHELATION; CHIRALITY; ELECTRON SPIN RESONANCE; ENZYME ANALYSIS; ENZYME SYNTHESIS; LIGAND BINDING; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033613983     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00505-9     Document Type: Article

References (55)

1. (a) Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563;
2. (b) Solomon, E. I.; Baldwin, M. J.; Lowery, M. D. Chem. Rev. 1992, 92, 521.
3. (a) Reinhammar, B. In Copper Proteins and Copper Enzymes, Vol. 3; Lontic R., Ed.; CRC Press: Boca Raton, FL, 1984; p. 1;
4. (b) Thurston, C. F. Microbiology 1994, 140, 19;
5. (c) Marzullo, L.; Cannio, R.; Giardina, P.; Santini, M. T.; Sannia, G. J. Biol. Chem. 1995, 270, 3823;
6. (d) Bollag, J. M. Met. Ions Biol. Syst. 1992, 28, 205.
7. (a) Kroneck, P. M. H.; Armstromg, F. A.; Merckle, H.; Marchesini, A. Adv. Chem. Ser. 1982, 200, 223;
8. (b) Chichiriccò, G.; Cerù, P.; M. D'Alessandro, A.; Oratore, A.; Avigliano, L. Plant Sci. 1989, 64, 61;
9. (c) Mondovì, B.; Avigliano, L. In Copper Proteins and Copper Enzymes, Vol. 3; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; p. 101.
10. (a) Ryden, L. In Copper Proteins and Copper Enzymes, Vol. 3; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; p. 37;
11. (b) Messerschmidt, A.; Huber, R. Eur. J. Biochem. 1990, 187, 341;
12. (c) Musci, G.; Carbonaro, M.; Adriani, A.; Lania, A.; Galtieri, A.; Calabrese, L. Biochem. Biophys. 1990, 279, 8.
13. (a) Messerschmidt, A.; Rossi, A.; Ladenstein, R.; Huber, R.; Bolognesi, M.; Gatti, G.; Marchesini, A.; Petruzzelli, R.; Finazzi-Agrò, A. J. Biol. Chem. 1989, 206, 513;
14. (b) Messerschmidt, A.; Ladenstein, R.; Huber, R.; Bolognesi, M.; Avigliano, L.; Petruzzelli, R.; Rossi, A.; Finazzi-Agrò, A. J. Mol. Biol. 1992, 224, 179;
15. (c) Messerschmidt, A.; Luecke, H.; Huber, H. J. Mol. Biol. 1993, 230, 997;
16. (d) Messerschmidt, A. In Bioinorganic Chemistry of Copper Karlin, K. D.; Tyeklar Z., Eds; Chapman & Hall: New York, 1996; p. 471;
17. (e) Messerschmidt, A. Adv. Inorg. Chem. 1994, 40, 121.
18. Zaitseva, I.; Zaitsev, V.; Card, G.; Moshkov, K.; Bax, B.; Ralph, A.; Lindley, P. J. Biol. Inorg. Chem. 1996, 1, 15.
19. Malkin, R.; Malmström, B. G. Adv. Enzymol. 1970, 33, 170.
20. Nguyen, H.-H. T.; Nakagawa, K. H.; Hedman, B.; Elliott, S. J.; Lidstrom, M. E.; Hodgson, K. O.; Chan, S. I. J. Am. Chem. Soc. 1996, 118, 12766.
21. (a) Carlin, K. D.; Gan, Q.-F; Farooq, A.; Liu, S.; Zubieta, J. Inorg. Chem. 1990, 29, 2085;
22. (b) Adams, H.; Bailey, N. A.; Dwyer, M. J. S.; Fenton, D. E.; Hellier, P. C.; Hempstead, P. D.; Latour, J. M. J. Chem. Soc., Dalton Trans. 1993, 1207;
23. (c) Meenakumari, S.; Tiwary, S. K.; Chakravarty, A. R. Inorg. Chem. 1994, 33, 2085;
24. (d) Frey, S. T.; Sun, H. H. J.; Murth, N. N.; Karlin, K. D. Inorg. Chim. Acta 1996, 242, 399;
25. (e) Singh, K.; Long, J. R.; Stavropoulos, P. Inorg. Chem. 1998, 37, 1073.
26. Monzani, E.; Casella, L.; Zoppellaro, G.; Gullotti, M.; Pagliarin, R.; Bonomo, R. P.; Tabbì, G.; Nardin, G.; Randaccio, L. Inorg. Chim. Acta 1998, 252/2, 180.
27. (a) Sorrell, T. N.; Borovik, A. S. J. Am. Chem. Soc. 1987, 109, 4255;
28. (b) Sorrell, T. N.; Vankai, V. A.; Garrity, M. L. Inorg. Chem. 1991, 30, 207;
29. (c) Sorrell, T. N.; Garrity, M. L. ibid. 1991, 30, 210;
30. (d) Oberhausen, K. J.; Richardson, J. F.; Buchanan, R. M.; Mc Cusker, J. K.; Hendrickson, D. N.; Latour, J. M. ibid. 1991, 30, 1357;
31. (e) Tolman, W. B.; Rardin, R. L.; Lippard, S. J. J. Am. Chem. Soc. 1989, 111, 4532;
32. (f) Lynch, W. E.; Kurtz Jr., D. M.; Wang, S.; Scott, R. A. ibid. 1994, 116, 11030;
33. (g) Sorrell, T. N.; Allen, W. E.; White, P. S. Inorg. Chem. 1995, 34, 952;
34. (h) Koolhaas, G. J. A. A.; Driessen, W. L.; Reedijk, J.; van der Plas, J. L.; de Graaff, R. A. G.; Gatteschi, D.; Kooijman, H.; Spek, A. L. ibid. 1996, 35, 1509.
35. Koning, W.; Geiger, R. Chem. Ber. 1970, 103, 788.
36. Castro, B.; Dormoy, J. R.; Dourtoglou, B.; Evin, G.; Selve, C.; Ziegler, J. C. Synthesis 1976, 751.
37. Fujita, E. Pure and Appl. Chem. 1981, A.53, 1141.
38. Dourtoglou, V.; Gross, B. Synthesis 1983, 572.
39. Asay, R. E.; Bradshaw, J. S.; Nielsen, S. F.; Thompson, M. D.; Snow, J. W.; Masihdas, D. R. K.; Izatt, R. M.; Christensen, J. J. J. Heterocycl. Chem. 1977, 14, 85.
40. Noordam, A.; Maat, L.; Beyerman, H. C. Recueil J. of the Royal Netherlands Chem. Soc. 1978, 97, 293.
41. Chen, S.; Richardson, J. F.; Buchanan, R. M. Inorg. Chem. 1994, 33, 2376.
42. (a) Fawcett, T. G.; Bernaducci, E. E.; Krogh-Jespersen, K.; Schugar, H. J. J. Am. Chem. Soc. 1980, 102, 2598;
43. (b) Bernaducci, E. E.; Schwindinger, W. F.; Hughey IV, J. L.; Krogh-Jespersen, K.; Schugar, H. J. ibid. 1981, 103, 1686.
44. (a) Casella, L.; Gullotti, M. J. Inorg. Biochem. 1983, 18, 19;
45. (b) Casella, L.; Gullotti, M. Inorg. Chem. 1983, 22, 242;
46. (c) Casella, L.; Gullotti, M. ibid. 1985, 24, 84.
47. (a) Amundsen, A. R.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6730;
48. (b) Downes, J. M.; Whelan, J.; Bosnich, B. Inorg. Chem. 1981, 20, 1081;
49. (c) Kennedy, B. P.; Lever, A. B. P. J. Am. Chem. Soc. 1973, 95, 6907.
50. Hataway, B. J. In Comprehensive Coordination Chemistry, Vol. 5; Wilkinson, G., Ed.; Pergamon Press: New York, 1987; p. 533.
51. (a) Casella, L.; Gullotti, M. Inorg. Chem. 1981, 20, 1306;
52. (b) Casella, L.; Gullotti, M.; Pacchioni, G. J. Am. Chem. Soc. 1982, 104, 2386.
53. Casella, L.; Gullotti, M.; Pallanza, G.; Buga, M. Inorg. Chem. 1991, 30, 221.
54. (a) Wayland, B. B.; Kapur, V. K. Inorg. Chem. 1974, 13, 2517;
55. (b) Kogane, T.; Hirota, R.; Abe, K.; Hirota, M. J. Chem. Soc., Perkin Trans. 2 1981, 652.