Synthesis of the first tricyclic homodetic peptide. Use of coordinated orthogonal deprotection to achieve directed ring closure

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 7179-7202

  Hirschmann, Ralph ^a   Yao, Wenqing ^a   Arison, Byron ^b   Maechler, Laurie ^c   Rosegay, Avery ^b   Sprengeler, Paul A ^a   Smith III, Amos B ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c MDS Inc   (Canada)

Author keywords

Cyclization; Peptide analogues mimetics; Protecting groups; Solid phase synthesis

Indexed keywords

HORMONE ANTAGONIST; PEPTIDE; RECEPTOR SUBTYPE; SOMATOSTATIN DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; HORMONE STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032543631     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00354-8     Document Type: Article

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45. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
46. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
47. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
48. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
49. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
50. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
51. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
52. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
53. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
54. 26. For reviews see: Fields, G. B.; Noble, R. L. (1990) Int. J. Peptide Protein Res. 35, 161. Benz, H. (1994) Synthesis 337. Typical examples are cleavage from the resin by: nucleophiles, Findeis, M. A.; Kaiser, E. T. (1989) J. Org. Chem. 54, 3478; mild acid, Rink, H. (1987) Tetrahedron Lett. 28, 3787; Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. (1988) Tetrahedron Lett. 29, 4005; Albericio, F.; Barany, G. (1991) Tetrahedron Lett. 32, 1015; base, Liu, Y. Z.; Ding, S. H.; Chu, J. Y.; Felix, A. M. (1990) Int. J. Peptide Protein Res. 35, 95; fluoride, Mullen, D. G.; Barany, G. (1987) Tetrahedron Lett. 28, 491; Ramage, R.; Barron, C. A.; Bielecki, S.; Holden, R.; Thomas, D. W. (1992) Tetrahedron 48, 499; and Pd(0) catalysis, Kunz, H.; Dombo, B. (1988) Angew. Chem. Int. Ed. Engl. 27, 711.
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61. 30. Tam, J. P. (1988) In Macromolecular Sequencing and Synthesis: Selected Methods and Applications, David H. Schlesinger, Ed., Alan R. Liss, Inc., New York, 153-184.
62. 31. Hoffmann, E.; Beck-Sickinger, A. G.; Jung, G. (1991) Liebigs Ann. Chem. 585-590. Schmidt, U.; Lieberknecht, A.; Griesser, H.; Utz, R.; Beuttler, T.; Bartkowiak, F. (1986) Synthesis 361. Ueda, K.; Waki, M.; Izumiya, N. (1987) Int. J. Peptide Protein Res. 30, 33. Schmidt, R.; Neubert, K. (1991) Int. J. Peptide Protein Res. 37, 502.
63. 31. Hoffmann, E.; Beck-Sickinger, A. G.; Jung, G. (1991) Liebigs Ann. Chem. 585-590. Schmidt, U.; Lieberknecht, A.; Griesser, H.; Utz, R.; Beuttler, T.; Bartkowiak, F. (1986) Synthesis 361. Ueda, K.; Waki, M.; Izumiya, N. (1987) Int. J. Peptide Protein Res. 30, 33. Schmidt, R.; Neubert, K. (1991) Int. J. Peptide Protein Res. 37, 502.
64. 31. Hoffmann, E.; Beck-Sickinger, A. G.; Jung, G. (1991) Liebigs Ann. Chem. 585-590. Schmidt, U.; Lieberknecht, A.; Griesser, H.; Utz, R.; Beuttler, T.; Bartkowiak, F. (1986) Synthesis 361. Ueda, K.; Waki, M.; Izumiya, N. (1987) Int. J. Peptide Protein Res. 30, 33. Schmidt, R.; Neubert, K. (1991) Int. J. Peptide Protein Res. 37, 502.
65. 31. Hoffmann, E.; Beck-Sickinger, A. G.; Jung, G. (1991) Liebigs Ann. Chem. 585-590. Schmidt, U.; Lieberknecht, A.; Griesser, H.; Utz, R.; Beuttler, T.; Bartkowiak, F. (1986) Synthesis 361. Ueda, K.; Waki, M.; Izumiya, N. (1987) Int. J. Peptide Protein Res. 30, 33. Schmidt, R.; Neubert, K. (1991) Int. J. Peptide Protein Res. 37, 502.
66. 32. (a) Cavelier-Frontin, F.; Pèpe, G.; Verducci, J.; Siri, D.; Jacquier, R. (1992) J. Am. Chem. Soc. 114, 8885.
67. (b) Kessler, H.; Haase, B. (1992) Int. J. Peptide Protein Res. 39, 36.
68. 33. Brady, S. F.; Varga, S. L.; Freidinger, R. M.; Schwenk, D. A.; Mendlowski, M.; Holly, F. W.; Veber, D. F. (1979) J. Org. Chem. 44, 3101.
69. 34. Yao, W., unpublished results.
70. 35. Hirschmann, R.; Yao, W.; Cascieri, M. A.; Strader, C. D.; Maechler, L.; Cichy-Knight, M. A.; Hynes, J., Jr.; Van Rijn, R. D.; Sprengeler, P. A.; Smith, A. B., III (1996) J. Med. Chem. 39, 2441.
71. 36. Lender, A.; Yao, W. Q.; Sprengeler, P. A.; Spanevello, R. A.; Furst, G. T.; Hirschmann, R.; Smith, A. B., III (1993) Int. J. Peptide Protein Res. 42, 509.
72. 37. Dangles, O.; Guibé, F.; Balavoine, G.; Lavielle, S.; Marquet, A. (1987) J. Org. Chem. 52, 4984.
73. 38. The binding affinity of 1 was determined as previously described; see reference 35.
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