An extended β-strand mimic for a larger artificial β-sheet

Journal of the American Chemical Society

Volumn 119, Issue 23, 1997, Pages 5413-5424

  Nowick, James S ^a   Pairish, Mason ^a   Lee, In Quen ^a   Holmes, Darren L ^a   Ziller, Joseph W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDRAZINO 2 METHOXYBENZOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HYDROGEN BOND; MOLECULAR MODEL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030811193     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963843s     Document Type: Article

References (69)

1. Kemp, D. O. Trends Biotechnol. 1990, 8, 249.
2. (b) Hölzemann, G. Kontakte 1991, 3.
3. (c) Hölzemann, G. Kontakte 1991, 55.
4. (d) Hirschmann, R. Angew. Chem., Int. Ed. Engt. 1991, 30, 1278.
5. (e) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039.
6. (f) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327.
7. (g) Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266.
8. (h) Zuckermann, R. N. Curr. Opin. Struct. Biol. 1993, 3, 580.
9. (i) Kahn, M. Synlett 1993, 821.
10. (j) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
11. (k) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
12. (l) Liskamp, R. M. J. Red. Trav. Chim. Pays-Bas 1994, 113, 1.
13. (m) Adang, A. E. P.; Hermkens, P. H. H.; Linders, J. T. M.; Ottenheijm, H. C. J.; van Staveren, C. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 63.
14. (n) Beeley, N. Trends Biotechnol. 1994, 12, 213.
15. (o) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169.
16. (p) Goodman, M.; Shao, H. Pure Appl. Chem. 1996, 68, 1303.
17. (q) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 25, 401.
18. (a) Kemp, D. S.; Bowen, B. R. In Tetrahedron Lett. 1988, 29, 5077.
19. (b) Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081.
20. (c) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650.
21. (a) Kemp, D. S.; Bowen, B. R. In Protein Folding: Deciphering the Second Half of the Genetic Code; Gieraseh, L. M., King, J., Eds.; American Association for the Advancement of Science: Washington, DC, 1990; pp 293-303.
22. (b) Kemp, D. S.; Muendel, C. C.; Blanchard, D. E.; Bowen, B. R. In Peptides: Chemistry, Structure and Biology: Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds.; ESCOM: Leiden, 1990; pp 674-676.
23. (c) Kemp, D. S.; Blanchard, D. E.; Muendel, C. C. In Peptides: Chemistry, Structure and Biology: Proceedings of the Twelfth American Peptide Symposium; Smith, J. A., Rivier, J. E., Eds.; ESCOM: Leiden, 1992; pp 319-322.
24. (a) Martin, S. F.; Austin, R. E.; Oalmann, C. J. Tetrahedron Lett. 1990, 31, 4731.
25. (b) Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Baker, W. R.; Condon, S. L.; deLara, E.; Rosenberg, S. H.; Spina, K. P.; Stein, H. H.; Cohen, J.; Kleinert, H. D. J. Med. Chem. 1992, 35, 1710.
26. (c) Baker, W. R.; Jae, H.-S.; Martin, S. F.; Condon, S. L.; Stein, H. H.; Cohen, J.; Kleinert, H. D. Bioorg. Med. Chem. Lett. 1992, 2, 1405.
27. (d) Martin, S. F.; Oalmann, C. J.; Liras, S. Tetrahedron 1993, 49, 3521.
28. (a) Smith, A. B., III; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1992, 114, 10672.
29. (b) Smith, A. B., III; Holcomb, R. C.; Guzman, M. C.; Keenan, T. P.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1993, 34, 63.
30. (c) Smith, A. B., III; Hirschmann, R.; Pasternak, A.; Akaishi, R.; Guzman, M. C.; Jones, D. R.; Keenan, T. P.; Sprengeler, P. A.; Darke, P. L.; Emini, E. A.; Holloway, M. K.; Schleif, W. A. J. Med. Chem. 1994, 37, 215.
31. (d) Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P., Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947.
32. (e) Smith, A. B.; Akaishi, R.; Jones, D. R.; Keenan, T. P.; Guzman, M. C.; Holcomb, R. C.; Sprengeler, P. A.; Wood, J. L.; Hirschmann, R.; Holloway, M. K. Biopolymers 1995, 37, 29.
33. (f) Smith, A. B.; Hirschmann, R.; Pasternak, A.; Guzman, M. C.; Yokoyama, A.; Sprengeler, P. A.; Darke, P. L.; Emini, E. A.; Schleif, W. A. J. Am. Chem. Soc. 1995, 117, 11113.
34. Michne, W. F.; Schroeder, J. D. Int. J. Peptide Protein Res. 1996, 47, 2.
35. Boumendjel, A.; Roberts, J. C.; Hu, E.; Pallai, P. V.; Rebek, J., Jr. J. Org. Chem. 1996, 61, 4434.
36. Schrader, T.; Kirsten, C. Chem. Commun. 1996, 2089.
37. Gante, J. Synthesis 1989, 405.
38. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568.
39. Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539.
40. (a) Liskamp, R. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 633.
41. (b) Moran, E. J.; Wilson, T. E.; Cho, C. Y.; Cherry, S. R.; Schultz, P. G. Biopolymers 1995, 37, 213.
42. (a) Nowick, J. S.; Lee, I. Q.; Mackin, G.; Pairish, M.; Shaka, A. J.; Smith, E. M.; Ziller, J. W. In Molecular Design and Bioorganic Catalysis; Wilcox, C. S., Hamilton, A. D., Eds.; Kluwer Academic: Dordrecht, Netherlands, 1996; pp 111-136.
43. (b) Smith, E. M.; Pairish, M.; Nowick, J. S. In Self-Assembly in Synthetic Chemistry; Wuest, J. D., Ed.; Kluwer Academic: Dordrecht, Netherlands, in press.
44. (a) Nowick, J. S.; Powell, N. A.; Martinez, E. J.; Smith, E. M.; Noronha, G. J. Org. Chem. 1992, 57, 3763.
45. (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.
46. (c) Nowick, J. S.; Mahrus, S.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 1066.
47. Nowick, J. S.; Smith, E. M.; Noronha, G. J. Org. Chem. 1995, 60, 7386.
48. Nowick, J. S.; Holmes, D. L.; Mackin, G.; Noronha, G.; Shaka, A. J.; Smith, E. M. J. Am. Chem. Soc. 1996, 118, 2764.
49. Auerbach, J.; Weissman, S. A.; Blacklock, T. J.; Angeles, M. R.; Hoogsteen, K. Tetrahedron Lett. 1993, 34, 931.
50. Demers, J. P.; Klaubert, D. H. Tetrahedron Lett. 1987, 28, 4933.
51. Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929.
52. Holmes, D. L.; Smith, E. M.; Nowick, J. S. Submitted to J. Am. Chem. Soc.
53. h exhibit the largest concentration-dependent changes in chemical shift.
54. Wagner, G.; Pardi, A.; Wüthrich, K. J. Am. Chem. Soc. 1983, 105, 5948.
55. (a) Wishart, D. A.; Sykes, B. D.; Richards, F. M. J. Mol. Biol. 1991, 222, 311.
56. (b) Wishart, D. A.; Sykes, B. D.; Richards, F. M. Biochemistry 1992, 31, 1647, and references contained therein.
57. Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986; pp 124-129.
58. (a) Ribeiro, A. A.; Goodman, M.; Naider, F. Int. J. Peptide Protein Research 1979, 14, 414.
59. (b) Stevens, E. S.; Sugawara, N.; Bonora, G. M.; Toniolo, C. J. Am. Chem. Soc. 1980, 102, 7048.
60. (c) Gellman, S. H.; Adams, B. R. Tetrahedron Lett. 1989, 30, 3381.
61. In competitive solvents, such as water and dimethyl sulfoxide, the chemical shifts of peptide amide protons exhibit different temperature dependencies: Solvent-exposed protons exhibit large temperature dependencies, while intramolecularly hydrogen-bonded (solvent-shielded) protons exhibit small temperature dependencies.
62. (a) Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
63. (b) Dyson, H. J.; Wright, P. E. Annu. Rev. Biophys. Biophys. Chem. 1991, 20, 519.
64. Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986; pp 166-168.
65. (a) Rajarathnam, K.; Sykes, B. D.; Kay, C. M.; Dewald, B.; Geiser, T.; Baggiolini, M.; Clark-Lewis, I. Science 1994, 264, 90.
66. (b) Ghadiri, M. R.; Kobayashi, K.; Granja, J. R.; Chadha, R. K.; McRee, D. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 93.
67. (c) Kobayashi, K.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95.
68. (d) Nesloney, C. L; Kelly, J W. J. Am. Chem. Soc. 1996, 118, 5836.
69. de Paulis, T.; Janowsky, A.; Kessler, R. M.; Clanton, J. A.; Smith, H. E. J. Med. Chem. 1988, 31, 2027.