Solid-phase synthesis of peptide mimetics with (E)-alkene amide bond replacements derived from alkenylaziridines

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1586-1587

  Wipf, Peter ^a   Henninger, Todd C ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PSEUDOPEPTIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030977733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701039     Document Type: Article

References (34)

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2. For recent reviews, see: (a) Horwell, D. C. Bioorg. Med. Chem. 1996, 4, 1573. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1. (c) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
3. For recent reviews, see: (a) Horwell, D. C. Bioorg. Med. Chem. 1996, 4, 1573. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1. (c) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
4. (a) Kessler, H.; Gratias, R.; Hessler, G.; Gurrath, M.; Müller, G. Pure Appl. Chem. 1996, 68, 1201.
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6. (a) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994, 59, 4875.
7. (b) Henninger, T.; Wipf, P. In Methods in Molecular Biology: Peptidomimetics; Walker, J. M., Kazmierski, W. M., Eds.; Humana Press: Totowa, NJ, in press.
8. (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Fujii, N.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 652.
9. (b) Fujii, N.; Nakai, K.; Tamamura, H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1995, 1359.
10. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
11. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
12. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
13. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
14. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
15. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
16. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
17. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
18. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
19. For other recent synthetic routes to (E)-alkene peptide isosteres, see: (a) Kranz, M.; Kessler, H. Tetrahedron Lett. 1996, 37, 5359. (b) Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280. (d) Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703. (e) Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291. (f) Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. (g) Bartlett, P. A.; Otake, A. J. Org. Chem. 1995, 60, 3107. (h) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64. (i) Wai, J. S.; Fisher, T. E.; Embrey, M. W. Tetrahedron Lett. 1995, 36, 3461. (j) McKinney, J. A.; Eppley, D. F.; Keenan, R. M. Tetrahedron Lett. 1994, 35, 5985.
20. Wang, S.-S. J. Am. Chem. Soc. 1973, 95, 1328.
21. (a) Bodanszky, M. Principles of Peptide Synthesis, 2nd ed.; Springer-Verlag: Heidelberg, 1993.
22. (b) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367.
23. (c) Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. J. Chem. Soc., Perkin Trans. 1 1996, 995.
24. Numerous examples of the use of the Wang resin in solid-phase organic synthesis can be found in several recent reviews: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527. (e) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
25. Numerous examples of the use of the Wang resin in solid-phase organic synthesis can be found in several recent reviews: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527. (e) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
26. Numerous examples of the use of the Wang resin in solid-phase organic synthesis can be found in several recent reviews: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527. (e) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
27. Numerous examples of the use of the Wang resin in solid-phase organic synthesis can be found in several recent reviews: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527. (e) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
28. Numerous examples of the use of the Wang resin in solid-phase organic synthesis can be found in several recent reviews: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527. (e) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
29. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
30. A similar reagent, leading to α,β-unsaturated amides, was recently reported: Johnson, C. R.; Zhang, B. Tetrahedron Lett. 1995, 36, 9253.
31. Preparation of 3 is described in the Supporting Information.
32. Brook, M. A.; Chan, T. H. Synthesis 1983, 201.
33. 13C NMR, IR, MS, and HRMS.
34. For a recent synthesis of hydroxyethylene peptide isosteres and vinylogous amino acids on solid support, see: Rotella, D. P. J. Am. Chem. Soc. 1996, 118, 12246.