Macrocyclic [Cu(I/II)(bite)](+/2+) (bite = biphenyldiimino dithioether): An example of fully-gated electron transfer and its biological relevance

Journal of the American Chemical Society

Volumn 119, Issue 38, 1997, Pages 8857-8868

  Flanagan, Scott ^a   Dong, Jun ^c   Haller, Kenneth ^b   Wang, Shengke ^c   Scheidt, W Robert ^b   Scott, Robert A ^c   Webb, Thomas R ^d   Stanbury, David M ^d   Wilson, Lon J ^a  

^a RICE UNIVERSITY   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

^c UNIVERSITY OF GEORGIA   (United States)

^d AUBURN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030819978     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9644034     Document Type: Article

References (67)

1. Taken in part from the following: Flanagan, J. S. Ph.D. Dissertation, Rice University, 1995.
2. Solomon, E. I. In Copper Coordination Chemistry: Biological & Inorganic Perspectives; Karlin, K. D., Zubieta, J., Eds.; Adenine Press: Guilderland, New York, 1983; pp 1-22.
3. Coggin, D. K.; González, J. A.; Kook, A. M.; Stanbury, D. M.; Wilson, L. J. Inorg. Chem. 1991, 30, 1115-1125.
4. Coggin, D. K.; González, J. A.; Kook, A. M.; Bergman, C.; Brennan, T. D.; Scheidt, W. R.; Stanbury, D. M.; Wilson, L. J. Inorg. Chem. 1991, 30, 1125-1134.
5. Knapp, S.; Keenan, T. P.; Zhang, X.; Fikar, R.; Potenza, J. A.; Schugar, H. J. J. Am. Chem. Soc. 1987, 109, 1882.
6. Knapp, S.; Keenan, T. P.; Liu, J.; Potenza, J. A.; Schugar, H. J. Inorg. Chem. 1990, 29, 2191.
7. Knapp, S.; Keenan, T. P.; Zhang, X.; Fikar, R.; Potenza, J. A.; Schugar, H. J. J. Am. Chem. Soc. 1990, 112, 3452-3464.
8. Groenveld, C. M.; van Rijn, J.; Reedijk, J.; Canters, G. W. J. Am. Chem. Soc. 1988, 110, 4893-4900.
9. Drew, M. G. B.; Cairns, C.; McFall, S. G.; Nelson, S. M. J. Chem. Soc., Dalton Trans. 1980, 2020-2027.
10. Drew, M. G. B.; Cairns, C.; Nelson, S. M.; Nelson, J. J. Chem. Soc., Dalton Trans. 1981, 942-948.
11. Goodwin, J. A.; Bodager, G. A.; Wilson, L. J.; Stanbury, D. M.; Scheidt, W. R. Inorg. Chem. 1989, 28, 35.
12. Goodwin, J. A.; Stanbury, D. M.; Wilson, L. J.; Eigenbrot, C. W.; Schiedt, W. R. Inorg. Chem. 1987, 109, 2979-2991.
13. Goodwin, J. A.; Wilson, L. J.; Stanbury, D. M.; Scott, R. A. Inorg. Chem. 1989, 28, 42-50.
14. Müller, E.; Bernardinelli, G.; Reedijk, J. Inorg. Chem. 1996, 35, 1952-1957.
15. Farnum, D. G.; Rasheed, K. J. Org. Chem. 1977, 42, 573-574.
16. Livingstone, S. E. J. Chem. Soc. 1956, 437-440.
17. Lindoy, L. F.; Smith, R. J. Inorg. Chem. 1981, 20, 1314-1316.
18. Rogers, D. Acta Crystallogr. 1981, A37, 734.
19. Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; DeClercq, J.-P.; Woolfson, M. M. MULTAN 11/82; University of York: York, England, July 1982.
20. Cromer, D. T.; Waber, J. T. In International Tables for X-Ray Crystallography; The Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.2B.
21. Ibers, J. A.; Hamilton, W. C. Acta. Crystallogr. 1964, 17, 781.
22. Cromer, D. T. In International Tables for X-Ray Crystallography; The Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.3.1.
23. Cruickshank, D. W. J. Acta. Crystallogr. 1949, 2, 154.
24. Frenz, B. A. In Computing in Crystallography; Schenk, H., Olthof-Hazelkamp, R., vanKonigsveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978; pp 64-71.
25. Scott, R. A. Methods Enzymol. 1985, 117, 414-459.
26. Bevington, P. R.; Robinson, D. K. Data Reduction and Error Analysis for the Physical Sciences; 2nd ed.; McGraw-Hill, Inc.: New York, 1992.
27. Guss, J. M.; Harrowell, P. R.; Murata, M.; Norris, V. A.; Freeman, H. C. J. Mol. Biol. 1986, 192, 361.
28. Shepard, W. E. B.; Anderson, B. F.; Lewandoski, D. A.; Norris, G. E.; Baker, E. N. J. Am. Chem. Soc. 1990, 112, 7817-7819.
29. Guss, J. M.; Bartunik, H. D.; Freeman, H. C. Acta Crystallogr. 1992, B48, 790-811.
30. Vallee, B. L.; Williams, R. J. P. Proc. Nat. Acad. Sci. U.S.A. 1968, 59, 498-505.
31. Lumry, R.; Eyring, H. J. Phys. Chem. 1954, 58, 110-120.
32. Malmström, B. G. Eur. J. Biochem. 1994, 223, 711-718.
33. Gray, H. B.; Malmström, B. G. Comments Inorg. Chem. 1983, 2, 203-209.
34. Williams, R. J. P. J. Mol. Catal. 1985, 30, 1-26.
35. Groenveld, C. M.; Canters, G. W. Eur. J. Biochem. 1985, 153, 559-564.
36. Groenveld, C. M.; Canters, G. W. Rev. Port. Quim. 1985, 27, 145.
37. Groenveld, C. M.; Dahlin, S.; Reinhammar, B.; Canters, G. W. J. Am. Chem. Soc. 1987, 109, 3247.
38. Guckert, J. A.; Lowery, M. D.; Solomon, E. I. J. Am. Chem. Soc. 1995, 117, 2817-2844.
39. Guss, J. M.; Freeman, H. C. J. Mol. Biol. 1983, 169, 521-563.
40. Anderson, O. P.; Becher, J.; Frydendahl, H.; Taylor, L. F.; Toftlund, H. J. Chem. Soc., Chem. Commun. 1986, 699-701.
41. Purcell, K. F.; Kotz, J. C. Inorganic Chemistry; W. B. Saunders Company: Philadelphia, 1977; pp 638-644.
42. Cross, L. C.; Klyne, W. Pure Appl. Chem. 1976, 45, 11-30.
43. Cheeseman, T. P.; Hall, D.; Waters, T. N. J. Chem. Soc. 1966, A, 1936.
44. Pignolet, L. H.; Taylor, R. P.; Horrocks, W. D., Jr. J. Am. Chem. Soc. 1969, 90, 5457.
45. Frydendahl, H.; Toftlund, H.; Becher, J.; Dutton, J. C.; Murray, K. S.; Taylor, L. F.; Anderson, O. P.; Tiekink, R. T. Inorg. Chem. 1995, 34, 4467-4476.
46. Brown, D. S.; Lee, J. D.; Melsom, B. G. A. Acta. Crystallogr. 1968, B24, 730.
47. Styka, M. C.; Smierciak, R. C.; Blinn, E. L.; DeSimone, R. E.; Passariello, J. V. Inorg. Chem. 1978, 17, 82.
48. Martin, M. J.; Endicott, J. F.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 1987, 26, 3012-3022.
49. Gewirth, A. A.; Solomon, E. I. J. Am. Chem. Soc. 1988, 110, 3811.
50. Brown, D. S.; Lee, J. D.; Melsom, B. G. A.; Hathaway, B. J.; Procter, I. M.; Tomlinson, A. A. G. J. Chem. Soc., Chem. Commun. 1967, 369.
51. Boas, J. F. In Copper Proteins and Copper Enzymes; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 1, p 2.
52. Dunn, B. C.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 1995, 34, 1954-1956 and references therein.
53. Salhi, C. A.; Yu, Q.; Heeg, M. J.; Villeneuve, N. M.; Juntunen, K. L.; Schroeder, R. R.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 1995, 34, 6053-6064 and references therein.
54. Vande Linde, A. M. Q.; Juntunen, K. L.; Mols, O.; Ksebati, M. B.; Ochrymowycz, L. A.; Rorabacher, D. B. Inorg. Chem. 1991, 30, 5037.
55. Corfield, P. W. R.; Ceccarelli, C.; Glick, M. D.; Moy, I. W.; Ochrymowycz, L. A.; Rorabacher, D. B. J. Am. Chem. Soc. 1985, 107, 2399-2404.
56. Rijn, J. v.; Driessen, W. L.; Reedijk, J.; Lehn, J. Inorg. Chem. 1984, 23, 3584-3588.
57. Sharpe, A. G. Inorganic Chemistry; Longman: London, 1986; p 611.
58. Williams, R. J. P. Eur. J. Biochem. 1995, 234, 363-381.
59. Kaim, W.; Schwederski, B. Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life; Wiley: Chichester, 1994; p 196.
60. Doine, H.; Yano, Y.; Swaddle, T. W. Inorg. Chem. 1989,28, 2319-2322.
61. Malmström, B. G. In New Trends in Bio-Inorganic Chemistry; Williams, R. J. P., DaSilva, R. J. R. F., Eds.; Academic Press: London, 1978; pp 59-78.
62. Reinhammar, B. R. M. Biochim. Biophys. Acta 1972, 275, 245-259.
63. Sykes, A. G. Adv. Inorg. Chem. 1991, 36, 377-408.
64. Büchi, F. N.; Bond, A. M.; Codd, R.; Huq, L. N.; Freeman, H. C. Inorg. Chem. 1992, 31, 5007-5014.
65. Armstrong, F. A.; Butt, J. N.; Govindaraju, K.; McGinnis, J.; Powls, R.; Sykes, A. G. Inorg. Chem. 1990, 29., 4858-4862.
66. Peisach, J.; Levine, W. G.; Blumberg, W. E. J. Biol. Chem. 1967, 242, 2847-2858.
67. Coggin, D. K. Ph.D. Dissertation, Rice University, 1990.