The propensities of amino acids to form parallel β-sheets

Journal of the American Chemical Society

Volumn 119, Issue 45, 1997, Pages 10903-10908

  Nowick, James S ^a   Insaf, Shabana ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; AMINO ACID; GLYCINE; LEUCINE; VALINE;

ARTICLE; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0030702048     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972074p     Document Type: Article

References (26)

1. Kim, C. A.; Berg, J. M. Nature 1993, 362, 267.
2. (a) Minor, D. L., Jr.; Kim, P. S. Nature 1994, 367, 660.
3. (b) Minor, D. L., Jr.; Kim, P. S. Nature 1994, 371, 264.
4. Smith, C. K.; Withka, J. M.; Regan, L. Biochemistry 1994, 33, 5510.
5. Smith, C. K.; Regan, L. Acc. Chem. Res. 1997, 30, 153.
6. For a study of the β-sheet forming propensities of different amino acids in a model system, see: Kemp, D. S. Trends Biotechnol. 1990, 8, 249.
7. Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 25, 401.
8. García-Moreno, E. B.; Dwyer, J. J.; Gittis, A. G.; Lattman, E. E.; Spencer, D. S.; Stiles, W. E. Biophys. Chem. 1997, 64, 211.
9. (a) Nowick, J. S.; Powell, N. A.; Martinez, E. J.; Smith, E. M.; Noronha, G. J. Org. Chem. 1992, 57, 3763.
10. (b) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89.
11. (c) Nowick, J. S.; Mahrus, S.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 1066.
12. (a) Nowick, J. S.; Smith, E. M.; Noronha, G. J. Org. Chem. 1995, 60, 7386.
13. (b) Nowick, J. S.; Holmes, D. L.; Mackin, G.; Noronha, G.; Shaka, A. J.; Smith, E. M. J. Am. Chem. Soc. 1996, 118, 2764.
14. (c) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413.
15. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Company: Rockford, IL, 1984.
16. Holmes, D. L.; Smith, E. M.; Nowick, J. S. J. Am. Chem. Soc. 1997, 119, 7665.
17. (a) Nowick, J. S.; Powell, N. A.; Nguyen, T. M.; Noronha, G. J. Org. Chem. 1992, 57, 7364.
18. (b) Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929.
19. Carpino, L. A.; Göwecke, S. J. Org. Chem. 1964, 29, 2824.
20. 1; related compounds that we have studied previously exhibit similar dimerization constants.
21. d.
22. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991; pp 35-37.
23. Chou, P. Y.; Fasman, G. D. Biochemistry 1974, 13, 211.
24. Smith, C. K.; Regan, L. Science 1995, 270, 980.
25. Blasie, C. A.; Berg, J. M. Biochemistry 1997, 36, 6218.
26. Twenty-four hours is not sufficient for the aminolysis to go to completion in the preparation of 1GV, 1AV, 1VV, and 1LV. In the preparation of these compounds, derivatives in which the top (valine) methyl ester groups are not aminolyzed are also isolated.