Metallopeptide design: Tuning the metal cation affinities with unnatural amino acids and peptide secondary structure

Journal of the American Chemical Society

Volumn 118, Issue 46, 1996, Pages 11349-11356

  Cheng, Richard P ^a   Fisher, Stewart L ^a   Imperiali, Barbara ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL ION;

AMINO ACID COMPOSITION; ARTICLE; BINDING AFFINITY; BINDING SITE; CIRCULAR DICHROISM; DRUG DESIGN; PROTEIN BINDING; PROTEIN STRUCTURE; SPECTROPHOTOMETRY;

EID: 0029912809     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9619723     Document Type: Article

References (41)

1. Rabanal, F.; DeGrado, W. F.; Dutton, P. L. J. Am. Chem. Soc. 1996, 118, 473-474.
2. Regan, L. Trends Biochem. Sci. 1995, 20, 280-285 and references therein.
3. (a) Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 3053-3054.
4. (b) Godwin, H. A.; Berg, J. M. J. Am. Chem. Soc. 1996, 118, 6514-6515.
5. Kazmierski, W. M. Int. J. Pept. Protein Res. 1995, 45, 241-247.
6. Gilbertson, S. R.; Chen, G.; McLoughlin, M. J. Am. Chem. Soc. 1994, 116, 4481-4482.
7. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616.
8. (b) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759.
9. (c) Imperiali, B.; Fisher, S. L. J. Am. Chem. Soc. 1991, 113, 8527-8528.
10. Rana, T. M.; Ban, M.; Hearst, J. E. Tetrahedron Lett. 1992, 33, 4521-4524.
11. Wilson, S. R.; Yasmin, A.; Wu, Y. J. Org. Chem. 1992, 57, 6941-6945.
12. Ruan, F.; Chen, Y.; Hopkins, P. B. J. Am. Chem. Soc. 1990, 112, 9403-9404.
13. (a) Summers, L. A. Adv. Heterocyclic Chem. 1978, 22, 1-69.
14. (b) McWhinnie, W. R.; Miller, J. D. Adv. Inorg. Chem. Radiochem. 1969, 12, 135-213.
15. (c) König, E. Coord. Chem. Rev. 1968, 3, 471-495.
16. (d) Lindoy, L. F.; Livingstone, S. E. Coord. Chem. Rev. 1961, 2, 173-193.
17. (e) Brandt, W. W.; Dwyer, F. P.; Gyarfas, E. C. Chem. Rev. 1954, 54, 959-1017.
18. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry; Jonh Wiley & Sons, Inc: Singapore, 1988.
19. Wuttke, D. S.; Gray, H. B.; Fisher, S. L.; Imperiali, B. J. Am. Chem. Soc. 1993, 115, 8455-8456.
20. (a) Struthers, M. D.; Cheng, R. P.; Imperiali, B. Science 1996, 271, 342-345.
21. (b) Struthers, M. D.; Cheng, R. P.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 3073-3081.
22. Chen, S.-T.; Wang, K.-T.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1986, 1514-1516.
23. Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161-214.
24. Imperiali, B.; Kapoor, T. M. Tetrahedron 1993, 49, 3501-3510.
25. Kraulis, P. J. J. Appl. Crystallogr. 1991, 24, 946-950.
26. Hutchinson, E. G.; Thornton, J. M. Protein Sci. 1994, 3, 2207-2216.
27. Imperiali, B.; Fisher, S. L.; Moats, R. A.; Prins, T. J. J. Am. Chem. Soc. 1992, 114, 3182-3188.
28. Dyson, H. J.; Rance, M.; Houghten, R. A.; Lerner, R. A.; Wright, P. E. J. Mol. Biol. 1988, 201, 161-200.
29. Fisher, S. L. Ph.D. Thesis, California Institute of Technology, 1993.
30. Prins, T. J. M.S. Thesis, California Institute of Technology, 1992.
31. Albertson, N. F. J. Am. Chem. Soc. 1946, 68, 450-453.
32. Experimental details for the preparation of compounds 6 and 7 are described in the Supporting Information.
33. Greenstein, J. P.; Winitz, W. D. Chemistry of the Amino Acids; John Wiley & Sons, New York, 1961; pp 1879-2155.
34. Connors, K. A. Binding Constants: the Measurement of Molecular Complex Stability; Wiley: New York, 1987.
35. Smith, R. M.; Martell, A. E. Critical Stability Constants, Volume 2, Amines; Plenum Press: New York, 1975; pp 235-262.
36. Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, 1994.
37. King, D. S.; Fields, C. G.; Fields, G. B. Int. J. Pept. Protein Res. 1990, 36, 255-266.
38. (a) Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203.
39. (b) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
40. Kuroda, H.; Chen, Y.-N.; Kimura, T.; Sakakibara, S. Int. J. Pept. Protein Res. 1992, 40, 294-299.
41. Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 4202-4207.