An examination of the steric effects of 5-tert-butylproline on the conformation of polyproline and the cooperative nature of type II to type I helical interconversion

Biopolymers

Volumn 53, Issue 3, 2000, Pages 249-256

  Beausoleil, Eric ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

5 tert butylproline; Amide isomer equilibrium; Conformational analysis; Polyproline

Indexed keywords

AMIDE; POLYMER; PROLINE DERIVATIVE; WATER;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; GEOMETRY; ISOMER; ISOMERISM; PROTEIN CONFORMATION; PROTEIN STABILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

PEPTIDES; PROLINE; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 0033950183     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(200003)53:3<249::AID-BIP4>3.0.CO;2-J     Document Type: Article

References (61)

1. Traub, W.; Shmueli, U. Nature 1963, 198, 1165.
2. Cowan, P. M.; McGavin, S. Nature 1955, 176, 501.
3. Torchia, D. A., Bovey, F. A. Macromolecules 1971, 4, 246.
4. Gornick, F.; Mandelkern, L.; Diorio, A. F.; Roberts, D. E. J. Am. Chem. Soc. 1964, 86, 2549.
5. Engel, J. Biopolymers 1966, 4, 945.
6. Farmer, B. L.; Hopfinger, A. J. Macromolecules 1974, 7, 793-796.
7. Mandelkern, L. In Poly-α-Amino Acids; Fasman, G. D., Ed.; Marcel Dekker: New York, 1967, ch 13.
8. Rabanal, F.; Ludevid, M. D.; Pons, M.; Giralt, E. Biopolymers 1993, 33, 1019.
9. Rothe, M.; Rott, H. Angew Chem Int Ed Engl 1976, 15, 770.
10. Dorman, D. E.; Torchia, D. A., Bovey, F. A. Macromolecules 1973, 6, 80.
11. Chao, Y.-Y. H.; Bersohn, R. Biopolymers 1978, 17, 2761.
12. Dukor, R. K.; Keiderling, T. A. Biospectroscopy 1996, 2, 83.
13. Harrington, W. F.; Sela, M. Biochim Biophys Acta 1958, 27, 24.
14. Steinberg, I. Z.; Harrington, W. F.; Berger, A.; Sela, M.; Katchalski, E. J Am Chem Soc 1960, 82, 5263.
15. Delaney, N. G.; Madison, V. J Am Chem Soc 1982, 104, 6635.
16. Delaney, N. G.; Madison, V. Int J Peptide Protein Res 1982, 19, 543.
17. Montelione, G. T.; Hughes, P.; Clardy, J.; Scheraga, H. A. J Am Chem Soc 1986, 108, 6765.
18. Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett 1993, 34, 381.
19. Beausoleil, E.; Sharma, R.; Michnick, S.; Lubell, W. D. In Peptides 1996 (Proceedings of the 24th European Peptide Symposium); Ramage, R., Epton, R., Eds.; ESCOM: Leiden, The Netherlands, 1997; pp 241-242.
20. Beausoleil, E.; Lubell, W. D. J Am Chem Soc 1996, 118, 12902.
21. Beausoleil, E.; Sharma, R.; Michnick, S.; Lubell, W. D. J Org Chem 1998, 63, 6572.
22. Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Peptide Res 1997, 50, 1.
23. Zhang, R.; Brownewell, F.; Madalengoitia, J. S. J Am Chem Soc 1998, 120, 3894.
24. McCafferty, D. G.; Friesen, D. A.; Danielson, E.; Wall, C. G.; Saderholm, M. J.; Erickson, B. W.; Meyer, T. J. Proc Natl Acad Sci USA 1996, 93, 8200-8204.
25. McCafferty, D. G.; Slate, C. A.; Nahkle, B. M.; Graham, H. D., Jr.; Austell, T. L.; Vachet, R. W.; Mullis, B. H.; Erickson, B. W. Tetrahedron 1995, 51, 9859.
26. Slate, C. A.; Striplin, D. R., Moss, J. A.; Chen, P. Erickson, B. W.; Meyer, T. J. J Am Chem Soc 1998, 120, 4885.
27. Overberger, C. G.; Jon, Y. S. J Polym Sci Polym Chem Ed. 1977 15, 1413-1421.
28. Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373.
29. Overberger, C. G.; Han, M. J. J Polym Sci Polym Chem Ed 1975, 13, 2251-2258.
30. Overberger, C. G.; Han, M. J. Pure Appl Chem 1974, 39, 33-44.
31. Ahn, K.-D.; Overberger, C. G. J Polym Sci Polym Chem Ed 1983, 21, 1699-1715.
32. Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J Polym Sci Polym Chem Ed 1983, 21, 1741-1749.
33. Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym Sci Polym Chem Ed 1983, 21, 1643-1656.
34. Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J Polym Sci Polym Chem Ed 1983, 21, 1751-1761.
35. McGrady, K. A. W.; Overberger, C. G. Polym J 1987, 19, 539-555.
36. McGrady, K. A. W.; Overberger, C. G. Polym Prepr (Am Chem Soc Div Polym Chem) 1987, 28, 429-430.
37. Tiba, O.; Overberger, C. G. J Polym Sci Pat A Polym Chem 1987, 25, 2941-2952.
38. Beausoleil, E.; L'Archevêque, B.; Bélec, L.; Atfani, M.; Lubell, W. D. J Org Chem 1996, 61, 9447.
39. Okabayashi, H.; Isemura, T.; Sakakibara, S. Biopolymers 1968, 6, 323.
40. Deber, C. M.; Bovey, F. A.; Carver, J. P.; Blout, E. R. J Am Chem Soc 1970, 92, 6191.
41. Hopfinger, A. J.; Walton, A. G. J Macromol Sci-Phys 1969, B3(1), 171.
42. Poznanski, J.; Ejchart, A.; Wierzchowski, K. L.; Ciurak, M. Biopolymers 1993, 33, 781 and refs therein.
43. Zhang, R.; Madalengoitia, J. S. Tetrahedron Lett 1996, 37, 6235.
44. Rink, H. Tetrahedron Lett 1987, 28, 3787.
45. Lapatsanis, L.; Milias, G.; Kleanthis, F.; Miltiadis, K. Synthesis 1983, 671.
46. Albericio, F.; Bofill, J. M.; El-Faham, A.; Kates, S. K. J Org Chem 1998, 63, 9678-9683.
47. Wellings, D. A.; Atherton, E. Methods Enzymol 1997, 289, 44-66.
48. Guy, C. A.; Fields, G. B. Methods Enzymol 1997, 289, 67-83.
49. Halab, L.; Lubell, W. D. J Org Chem 1999, 64, 3312-3321.
50. Van Der Auwera, C.; Anteunis, M. J. O. Int J Peptide Protein Res 1987, 29, 574-588.
51. Tung, R. D.; Rich, D. H. J Am Chem Soc 1985, 107, 4342-4343.
52. Lloyd-Williams, P.; Merzouk, A.; Guibé, F.; Albericio, F.; Giralt, E. Tetrahedron Lett 1994, 35, 4437-4440.
53. Fields, G. B.; Prockop, D. Biopolymers 1996, 40, 345.
54. Dambaugh, T.; Henennessey, K.; Chamnankit, L.; Keiff, E. Proc Natl Acad Sci USA 1984, 81, 7632-7636.
55. Reviewed in Siligardi, G.; Drake, A. F. Biopolymers (Peptide Sci) 1995, 37, 281-292.
56. Voyer, N.; Lamothe, J. Tetrahedron 1995, 54, 9241-9284.
57. Isied, S. S.; Ogawa, M. Y.; Wishart, J. F. Chem Rev 1992, 92, 381-394.
58. Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.; Armand, P.; Bradley, E. K.; Truong, K. T. V.; Dill, K. A.; Cohen, F. E.; Zuckermann, R. N. Proc Natl Acad. Sci USA 1998, 95, 4303-4308.
59. Armand, P.; Kirshenbaum, K.; Goldsmith, R. A.; Farr-Jones, S.; Barron, A. E.; Truong, K. T. V.; Dill, K. A.; Mierke, D. F.; Cohen, F. E.; Zuckermann, R. N.; Bradley, E. K. Proc Natl Acad Sci USA 1998, 95, 4309-4314.
60. Murphy, J. E.; Uno, T.; Hamer, J. D.; Cohen, F. E.; Dwarki, V.; Zuckermann, R. N. Proc Natl Acad Sci USA 1997, 94, 1517-1522.
61. Slate, C. A.; Binstead, R. A.; Meyer, T. J.; Erickson, B. W. Lett Peptide Sci 1999, 6, 61.