Metallocyclopeptide complexes with M(II)(S·Cys)4 chromophores

Inorganic Chemistry

Volumn 39, Issue 11, 2000, Pages 2306-2313

  Nivorozhkin, Alexander L ^a   Segal, Brent M ^a   Musgrave, Kristin B ^c   Kates, Steven A ^b,d   Hedman, Britt ^c   Hodgson, Keith O ^c   Holm, R H ^a  

^a HARVARD UNIVERSITY   (United States)

^b PE Biosystems   (United States)

^c SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

^d Consensus Pharmaceuticals ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METALLOPROTEIN; COBALT; CYCLO(LYS1,12)(GLN CYS GLY VAL CYS GLY LYS CYS ILE ALA CYS LYS); CYCLO(LYS1,12)(GLN-CYS-GLY-VAL-CYS-GLY-LYS-CYS-ILE-ALA-CYS-LYS); CYCLOPEPTIDE; CYSTEINE;

ARTICLE; CHROMATOPHORE; CRYSTAL STRUCTURE; GEL PERMEATION CHROMATOGRAPHY; REACTION ANALYSIS; SOLID PHASE EXTRACTION; SPECTROPHOTOMETRY; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS; AMINO ACID SEQUENCE; BINDING SITE; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS; PROTEIN CONFORMATION; RADIODENSITOMETRY;

AMINO ACID SEQUENCE; BINDING SITES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COBALT; CYSTEINE; DENSITOMETRY, X-RAY; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; PROTEIN CONFORMATION;

EID: 0034729044     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic990421l     Document Type: Article

References (63)

1. Camarero, J. A.; Pavel, J.; Muir, T. W. Angew. Chem., Int. Ed. Engl. 1998, 37, 347.
2. Haubner, R.; Finsinger, D.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1375.
3. Rizo, J.; Gierasch, L. Annu. Rev. Biochem. 1992, 61, 387.
4. Yamazaki, T.; Said-Nejad, O. E.; Schiller, P. W.; Goodman, M. Biopolymers 1991, 31, 887.
5. Al-Obedi, F.; Castrucci, A. M. del L.; Hadley, M. E.; Hruby, V. J. J. Med. Chem. 1989, 32, 2555.
6. Goldenberg, D. P. J. Cell. Biochem. 1985, 29, 321.
7. Goldenberg, D. P.; Greighton, T. E. J. Mol. Biol. 1984, 179, 527.
8. Haas, K.; Ponikwar, W.; Nöth, H.; Beck, W. Angew. Chem., Int. Ed. 1998, 37, 1086.
9. Comba, P.; Cusack, R.; Fairlie, D. P.; Gahan, L. R.; Hanson, G. R.; Kazmaier, U.; Ramlow, A. Inorg. Chem. 1998, 37, 6721.
10. Tuchscherer, G.; Lehmann, C.; Mathieu, M. Angew. Chem., Int. Ed. 1998, 37, 2990.
11. For a recent example of metal binding to a cyclic cysteinyl peptide, cf.: Tanaka, K.; Shigemori, K.; Shionoya, M. Chem. Commun. 1999, 2475.
12. Regan, L. Annu. Rev. Biophys. Biomol. Struct. 1993, 22, 257.
13. Regan, L. Trends Biochem. Sci. 1995, 20, 280.
14. Gibney, B. R.; Rabanal, F.; Dutton, P. L. Curr. Opin. Chem. Biol. 1997, 1, 537.
15. Holm, R. H.; Kennepohl, P.; Solomon, E. I. Chem. Rev. 1996, 96, 2239.
16. Berg, J. M.; Shi, Y. Science 1996, 271, 1081.
17. Beinert, H.; Holm, R. H.; Münck, E. Science 1997, 277, 653.
18. Dance, I. G. Polyhedron 1986, 5, 1037.
19. Blower, P. J.; Dilworth, J. R. Coord. Chem. Rev. 1987, 76, 121.
20. Krebs, B.; Henkel, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 769.
21. Volbeda, A.; Charon, M.-H.; Piras, C.; Hatchikian, E. C.; Frey, M.; Fontecilla-Camps, J. C. Nature 1995, 373, 580.
22. Volbeda, A.; Garsin, E.; Piras, C.; de Lacey, A. L.; Fernandez, V. M.; Hatchikian, E. C.; Frey, M.; Fontecilla-Camps, J. C. J. Am. Chem. Soc. 1996, 118, 12989.
23. Higuchi, Y.; Yagi, T.; Yasuoka, N. Structure 1997, 5, 1671.
24. Holah, D. G.; Coucouvanis, D. J. Am. Chem. Soc. 1975, 97, 6917.
25. Swenson, D.; Baenziger, N. C.; Coucouvanis, D. J. Am. Chem. Soc. 1978, 100, 1932.
26. Yamamura, T.; Miyame, H.; Katayama, Y.; Sasaki, Y. Chem. Lett. 1985, 269.
27. Rosenfield, S. G.; Armstrong, W. H.; Mascharak, P. K. Inorg. Chem. 1986, 25, 3014.
28. Snyder, B. S.; Rao, Ch. P.; Holm, R. H. Aust. J. Chem. 1986, 39, 963.
29. Baidya, N.; Marscharak, P. K.; Stephan, D. W.; Campagna, C. F. Inorg. Chim. Acta 1990, 177, 233.
30. Fox, S.; Wang, Y.; Silver, A.; Millar, M. J. Am. Chem. Soc. 1990, 112, 3218.
31. Leussing, D. L.; Alberts, G. S. J. Am. Chem. Soc. 1960, 82, 4458.
32. Kowal, A. T.; Zambrano, I. C.; Moura, I.; Moura J. J. G.; Le Gall, J.; Johnson M. K. Inorg. Chem. 1988, 27, 1162.
33. This statement excludes mononuclear Ni(II) complexes with unsaturated ligands such as dithiolenes, dithiooxalate, dithiosquarate, and dithiotropolonate.
34. Nivorozhkin, A.; Kates, S. A.; Holm, R. H. In Peptides 1998; Bajkusz, S., Hudecz, F., Eds.; Akadémiai Kiadó: Budapest, 1999; pp. 522-523.
35. 2-o-xyl, o-xylyl-α,α′-dithiolate(2-); TFA, trifluoroacetic acid; TIS, triisopropylsilane; XAS, X-ray absorption spectroscopy.
36. Kates, S. A.; Sole, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549.
37. Londo, T. R.; Kehoe, T.; Kates, S. A.; Hantman, S.; Gordon, N. F. Lett. Peptide Sci. 1998, 5, 285.
38. Atherton, D. In Techniques in Protein Chemistry; Hugh, T. E., Ed.; Academic Press: New York, 1989; pp 273-283.
39. Cramer, S. P.; Tench, O.; Yocum, M.; George, G. N. Nucl. Instr. Methods A 1988, 266, 586.
40. DeWitt, J. G.; Bentsen, J. G.; Rosenzweig, A. C.; Hedman, B.; Green, J.; Pilkington, S.; Papaefthymiou, G. C.; Dalton, H.; Hodgson, K. O.; Lippard, S. J. J. Am. Chem. Soc. 1991, 113, 9219.
41. Filipponi, A.; Di Cicco, A.; Tyson, T. A.; Natoli, C. R. Solid State Commun. 1991, 78, 265.
42. Westre, T. E.; Di Cicco, A.; Filipponi, A.; Natoli, C. R.; Hedman, B.; Solomon, E. I.; Hodgson, K. O. J. Am. Chem. Soc. 1995, 117, 1566.
43. Filipponi, A.; Di Cicco, A.; Natoli, C. R. Phys. Rev. B 1995, 52, 15122, 15135.
44. Cavelier-Frontin, F.; Pèpe, G.; Verducci, J.; Siri, D.; Jacquier, R. J. Am. Chem. Soc. 1992, 114, 8885.
45. Lovenberg, W.; Sobel, B. E. Proc. Natl. Acad. Sci. U.S.A. 1965, 54, 193.
46. Lane, R. W.; Ibers, J. A.; Frankel, R. B.; Papaefthymiou, G. C.; Holm, R. H. J. Am. Chem. Soc. 1977, 99, 84.
47. May, S. W.; Kuo, J.-Y. Biochemistry 1978, 17, 3333.
48. Hagen, K. S.; Holm, R. H. Inorg. Chem. 1984, 23, 418.
49. Krizek, B. A.; Merkle, D. L.; Berg, J. M. J. Am. Chem. Soc. 1993, 32, 937.
50. Tremel, W.; Krebs, B.; Henkel, G. Angew. Chem., Int. Ed. Engl. 1984, 96, 604.
51. Tremel, W.; Kriege, M.; Krebs, B. Inorg. Chem. 1988, 27, 3886.
52. Shulman, R. G.; Yafet, Y.; Eisenberger, P.; Blumberg, W. E. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 1284.
53. Bair, R. A.; Goddard, W. A. Phys. Rev. 1980, B22, 2767.
54. Westre, T. E.; Kennepohl, P.; DeWiti, J. G.; Hedman, B.; Hodgson, K. O.; Solomon, E. I. J. Am. Chem. Soc. 1997, 119. 6297.
55. Eidsness, M. K.; Sullivan, R. J.; Scott, R. A. In The Bioinorganic Chemistry of Nickel; Lancaster, J. R., Jr., Ed.; VCH: New York, 1988, Chapter 4.
56. Cramer, S. P. Eidsness, M. K.; Pan, W. H.; Morton, T. A.; Ragsdale, S. W.; DerVartanian, D. V.; Ljungdahl, L. G.; Scott, R. A. Inorg. Chem. 1987, 26, 2477.
57. Colpas, G. J.; Maroney, M. J.; Bagyinka, C.; Kumar, M.; Willis, W. S.; Suib, S. L.; Baidya, N.; Mascharak, P. K. Inorg. Chem. 1991, 30, 920.
58. Maroney, M. J.; Colpas, G. J.; Bagyinka, C.; Baidya, N.; Mascharak, P. K. J. Am. Chem. Soc. 1991, 113, 3962.
59. Kobayashi, A.; Sasaki, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2650.
60. Baker, D. J.; Goodall, D. C.; Moss, D. S. Chem. Commun. 1969, 325.
61. Barclay, G. A.; McPartlin, E. M.; Stephenson, N. C. Acta Crystallogr. 1969, B25, 1262.
62. Tremel, W.; Krebs, B.; Henkel, G. Angew. Chem., Int. Ed. Engl. 1984, 23, 634.
63. Dance, I. G. J. Am. Chem. Soc. 1979, 101, 6264.