Stabilization of a cis amide bond in a host-guest complex

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10220-10227

  Pernía, Glen J ^a   Kilburn, Jeremy D ^a   Essex, Jonathan W ^a   Mortishire Smith, Russell J ^b   Rowley, Michael ^b  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; COMPLEX FORMATION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; THEORY;

EID: 0029955112     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9607805     Document Type: Article

References (54)

1. Schultz, G. E.; Schirman, R. H. Principles of Protein Structure; Springer-Verlag: New York, 1979.
2. Radzicka, A.; Pedersen, L.; Wolfenden, R. Biochemistry 1988, 27, 4538-4541.
3. Jorgensen, W. L.; Gao, J. J. Am. Chem. Soc. 1988, 110, 4212-4216.
4. Stewart, D. E.; Sarkar, A.; Wampler, J. E. J. Mol. Biol. 1990, 214, 253-260.
5. (a) Mierke, D. F.; Yamazaki, T.; Said-Nejad, O. E.; Felder, E. R.; Goodman, M. J. Am. Chem. Soc. 1989, 111, 6847-6849.
6. (b) Kessler, H.; Anders, U.; Schudok, M. J. Am. Chem. Soc. 1990, 112, 5908-5916.
7. (c) Kukumaran, D. K.; Prorok, M.; Lawrence, D. S. J. Am. Chem. Soc. 1991, 113, 706-707.
8. (d) Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861.
9. Bairaktari, E.; Mierke, D. F.; Mammi, S.; Peggion, E. J. Am. Chem. Soc. 1990, 112, 5383.
10. (a) Schreiber, S. L. Science 1991, 251, 283-287.
11. (b) Fischer, G.; Schmid, F. X. Biochemistry 1990, 29, 2205-2209.
12. A preliminary account of some of this work has been published: Pernia, G. J.; Kilburn, J. D.; Rowley, M. J. Chem. Soc., Chem. Commun. 1995, 305-306.
13. For recent reviews on molecular recognition, see: (a) Dowden, J.; Kilburn, J. D.; Wright, P. Contemp. Org. Synth. 1995, 2, 289. (b) Molecular Recognition (Tetrahedron Symposia No. 56). Hamilton, A. D., Ed.; Tetrahedron 1995, 51. (c) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383.
14. For recent reviews on molecular recognition, see: (a) Dowden, J.; Kilburn, J. D.; Wright, P. Contemp. Org. Synth. 1995, 2, 289. (b) Molecular Recognition (Tetrahedron Symposia No. 56). Hamilton, A. D., Ed.; Tetrahedron 1995, 51. (c) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383.
15. For recent reviews on molecular recognition, see: (a) Dowden, J.; Kilburn, J. D.; Wright, P. Contemp. Org. Synth. 1995, 2, 289. (b) Molecular Recognition (Tetrahedron Symposia No. 56). Hamilton, A. D., Ed.; Tetrahedron 1995, 51. (c) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383.
16. For recent reviews on molecular recognition, see: (a) Dowden, J.; Kilburn, J. D.; Wright, P. Contemp. Org. Synth. 1995, 2, 289. (b) Molecular Recognition (Tetrahedron Symposia No. 56). Hamilton, A. D., Ed.; Tetrahedron 1995, 51. (c) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383.
17. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
18. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
19. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
20. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
21. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
22. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
23. For recent work on synthetic receptors for amino acid and peptide derivatives see, for example: (a) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 848. (b) Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089. (c) Kuroda, Y.; Kato, Y.; Higashioli, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M ; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. (d) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. (e) Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 36, 3051. (f) Flack, S. S.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 3409. (g) Yoon, S. S.; Still, W. C. Tetrahedron 1995, 51, 567.
24. (a) Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369.
25. (b) Smith, P. J.; Reddington, M. V.; Wilcox, C. S. Tetrahedron Lett. 1992, 33, 6085.
26. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
27. (b) Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
28. Gronowitz, S.; Bobosik, V.; Lawitz, K. Chem. Scri. 1984, 23, 120.
29. (a) Dyson, G. M.; George, H. J. J. Am. Chem. Soc. 1924, 1702.
30. (b) Rasmussen, C. R.; Villani, Jr., F. J.; Weaner, L. E.; Reynolds, B. E.; Hood, A. R.; Hecker, L. R.; Nortey, S. O.; Hanslin, A.; Costanzo, M. J.; Powell, E. T.; Molinari, A. J. Synthesis 1988, 456.
31. (c) Scröeder, D. C. Chem. Rev. 1955, 55, 193.
32. Wilcox, C. S. Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Durr, H., Eds.; VCH: Weinheim, 1991; pp 123-143.
33. Kypa, E. P.; Helgeson, R. C.; Madan, K.; Gokel, G. W.; Tarnowski, T. L.; Moore, S. S.; Cram, D. J. J. Am. Chem. Soc. 1977, 199, 2564.
34. Jeener, J.; Meier, B. H.; Backmann, P.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
35. Rance, M. J. Magn. Reson. 1987, 74, 557.
36. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 63, 207.
37. Rance, M.; Sorensen, O. W.; Bodenhausen, G.; Wagner, E. R. R.; Wüthrich, K. Biochem. Biophys. Res. Commun. 1983, 117, 479.
38. To eliminate possible errors in interpretation caused by artefacts or spurious intensities, ROESY spectra were acquired with three different transmitter offsets (7.5, 5.0, and 2.5 ppm), each with two mixing times (200 and 400 ms). Each spectrum exhibited qualitatively comparable intensities for the key structure defining ROEs. Spin-lock field strength and temperature also had a minimal effect on the relative ROE intensities.
39. Dyson, H. J.; Wright, P. E. 2-Dimensional NMR Spectroscopy, Croasmun, Carlson, Eds.; VCH: 1994; p 672.
40. Tripos, Inc.: St. Louis, Missouri.
41. MacroModel V5.0; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
42. (a) Jorgensen, W. L.; Tirado-Rives, J. J. Am. Chem. Soc. 1988, 110, 1657.
43. (b) Jorgensen, W. L.; Nguyen, T. B. J. Comput. Chem. 1993, 14, 195.
44. (c) Duffy, E. M.; Severance, D. L.; Jorgensen, W. L. Isr. J. Chem. 1993, 33, 323.
45. (d) Jorgensen, W. L. J. Phys. Chem. 1986, 90, 6379.
46. Still, W. C.; Tempczyk, A.; Hawley, R. C. J. Am. Chem. Soc. 1990, 112, 6127.
47. -1).
48. (a) Connors, K. A. Binding Constants, The Measurement of Molecular Complex Stability; Wiley: 1987; pp 24-28.
49. (b) Job, A. Annales de Chimie 1928, 9, 113.
50. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327.
51. Berendsen, J. H. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684.
52. Atkins, P. W. Physical Chemistry, 3rd ed.; OUP: Oxford, 1986; p 621.
53. Weast, R. C. Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1980.
54. Tropp, J. J. Chem. Phys. 1980, 72, 6035.