IBTM-containing gramicidin S analogues: Evidence for IBTM as a suitable type II' β-turn mimetic

Journal of the American Chemical Society

Volumn 119, Issue 44, 1997, Pages 10579-10586

  Andreu, David ^a   Ruiz, Sergi ^a   Carreño, Cristina ^a   Alsina, Jordi ^a   Albericio, Fernando ^a   Jiménez, María Angeles ^b   De La Figuera, Natalia ^c   Herranz, Rosario ^c   García López, María Teresa ^c   González Muñiz, Rosario ^c  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUTO DE ESTRUCTURA DE LA MATERIA   (Spain)

^c CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GRAMICIDIN DERIVATIVE; GRAMICIDIN S;

ARTICLE; CONFORMATION; DIASTEREOISOMER; DRUG STRUCTURE;

EID: 16944365743     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9705755     Document Type: Article

References (34)

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2. Parts of this work have been previously reported in preliminary form: (a) De la Figuera, N.; Jiménez, M. A.; Biacs, M.; Garća-López, M. T.; Gonzdlez-Muniz, R.; Andreu, D. In Peplides 1994: Proceedings of the Twenty-Third European Peptide Symposium; Maia, H. L. S., Ed.; ESCOM Science Publishers: Leiden, The Netherlands, 1994; pp 702-703. (b) Andreu, D.; Ruiz, S.; Carreño, C.; Alsina; J.; Albericio, F.; Jiménez, M. A.; De la Figuera, N.; Herranz, R.; García-López, M. T.; González-Mun̄iz, R. In Peptides 1996: Proceedings of the Twenty-Fourth European Peptide Symposium; Ramage, R., Epton, R., Eds.; Mayflower Worldwide Ltd.: Kingswinford, England, 1997; in press.
3. Parts of this work have been previously reported in preliminary form: (a) De la Figuera, N.; Jiménez, M. A.; Biacs, M.; Garća-López, M. T.; Gonzdlez-Muniz, R.; Andreu, D. In Peplides 1994: Proceedings of the Twenty-Third European Peptide Symposium; Maia, H. L. S., Ed.; ESCOM Science Publishers: Leiden, The Netherlands, 1994; pp 702-703. (b) Andreu, D.; Ruiz, S.; Carreño, C.; Alsina; J.; Albericio, F.; Jiménez, M. A.; De la Figuera, N.; Herranz, R.; García-López, M. T.; González-Mun̄iz, R. In Peptides 1996: Proceedings of the Twenty-Fourth European Peptide Symposium; Ramage, R., Epton, R., Eds.; Mayflower Worldwide Ltd.: Kingswinford, England, 1997; in press.
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8. For recent reviews on peptide conformation mimetics see: (a) Holzemann, G. Kontakte 1991, 3-12, 55-63. (b) Kahn, M. Synlett 1993, 821-826. (c) 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, 3039-3049. (d) Liskamp, R. M. J. Red. Trav. Chim, Pays-Bas 1994, 113, 1-19.
9. For recent reviews on peptide conformation mimetics see: (a) Holzemann, G. Kontakte 1991, 3-12, 55-63. (b) Kahn, M. Synlett 1993, 821-826. (c) 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, 3039-3049. (d) Liskamp, R. M. J. Red. Trav. Chim, Pays-Bas 1994, 113, 1-19.
10. For recent reviews on peptide conformation mimetics see: (a) Holzemann, G. Kontakte 1991, 3-12, 55-63. (b) Kahn, M. Synlett 1993, 821-826. (c) 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, 3039-3049. (d) Liskamp, R. M. J. Red. Trav. Chim, Pays-Bas 1994, 113, 1-19.
11. For recent reviews on peptide conformation mimetics see: (a) Holzemann, G. Kontakte 1991, 3-12, 55-63. (b) Kahn, M. Synlett 1993, 821-826. (c) 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, 3039-3049. (d) Liskamp, R. M. J. Red. Trav. Chim, Pays-Bas 1994, 113, 1-19.
12. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
13. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
14. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
15. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
16. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
17. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
18. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
19. Other representative examples of β-tum mimetics include: (a) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860-866. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147-6149. (d) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175-4178. (e) Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400. (f) Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091-4092. (h) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. (i) Slomczynska, U.; Chalmer, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
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