A systematic approach to the solid-phase synthesis of linear and cyclic pseudopeptide libraries containing Ψ[CH2NH] amide bond surrogates

Journal of Peptide Research

Volumn 49, Issue 1, 1997, Pages 3-14

  Wen, James J ^a   Spatola, Arno F ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

Combinatorial synthesis; Cyclization; Enkephalin analogs; Pseudopeptide; Reduced peptide bond; Solid phase synthesis

Indexed keywords

PSEUDOPEPTIDE;

ARTICLE; BINDING KINETICS; DIAGNOSTIC APPROACH ROUTE; PEPTIDE ANALYSIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RACEMIC MIXTURE; STRUCTURE ANALYSIS;

EID: 0030913670     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1997.tb01115.x     Document Type: Article

References (34)

1. Reviews: (a) Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. & Gordon, E.M. (1994) J. Med. Chem. 37, 1233-1251; (b) Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. & Gordon, E.M. (1994) J. Med. Chem. 37, 1386-1401
2. Reviews: (a) Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. & Gordon, E.M. (1994) J. Med. Chem. 37, 1233-1251; (b) Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A. & Gordon, E.M. (1994) J. Med. Chem. 37, 1386-1401
3. Kessler, H. (1982) Angew. Chem.. Int. Ed. Engl. 21, 512-523
4. Spatola, A.F. (1983) in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins (B. Weinstein, ed.), vol. VII, pp. 267-357, Marcel Dekker, New York
5. Spatola, A.F., Darlak, K. & Romanovskis, P. (1993) in Peptides: Chemistry, Structure and Biology, Proceedings of the Thirteenth American Peptide Symposium (Hodges. R.S. & Smith, J.A., eds.), pp. 981-983, ESCOM, Leiden
6. Preliminary accounts of this work were presented as follows: (a) Wen, J.J. & Spatola, A.F. 'Synthesis and Characterization of Pseudopeptide Libraries,' Poster presentation, 207th ACS, San Diego, CA, March, 1994; (b) Wen, J.J., Yankeelov, T. & Spatola, A.F. 'Pseudopeptide Library: A Systematic Approach,' Poster presentation, 14th American Peptide Symposium, Columbus, Ohio, June, 1995
7. Preliminary accounts of this work were presented as follows: (a) Wen, J.J. & Spatola, A.F. 'Synthesis and Characterization of Pseudopeptide Libraries,' Poster presentation, 207th ACS, San Diego, CA, March, 1994; (b) Wen, J.J., Yankeelov, T. & Spatola, A.F. 'Pseudopeptide Library: A Systematic Approach,' Poster presentation, 14th American Peptide Symposium, Columbus, Ohio, June, 1995
8. Szelke, M., Leekie, B., Hallett, A., Jones, D.M., Sueiras, J., Atrash, B. & Lever, A.F. (1982) Nature (London) 299, 555-557
9. Coy, D.H., Heinz-Erian, P., Jiang, N.Y., Sasaki, Y., Taylor, J., Moreau, J.P., Wolfrey, W.T., Gardner, J.D. & Jensen, R.T. (1988) J. Biol. Chem. 263, 5056-5060
10. Martinez, J., Bali, J.P., Rodriguez, M., Castro, B., Magous, R., Laur, J. & Lignon, M.F. (1985) J. Med. Chem. 28, 1874-1879
11. Qian, J.M., Coy, D.H., Gardner, J.D. & Jensen, R.T. (1989) J. Biol. Chem. 264, 16667-16671
12. Haffar, B.M., Hocart, S.J., Coy, D.H., Mantey, S., Chiang, H.C. & Jensen, R.T. (1991) J. Biol. Chem. 266, 316-322
13. Fehrentz, J.A. & Castro, B. (1983) Synthesis 676-678
14. Spatola, A.F., Anwer, M.K., Rockwell, A.L. & Gierasch, L.M. (1986) J. Am. Chem. Soc. 108, 825-831
15. Rovero, P., Quartara, L., & Fabbri, G. (1991) Tetrahedron Lett. 32, 2639
16. (a) Furka, A., Sebestyen, F., Asgedom, M. & Dibo, G. (1991) Int. J. Peptide and Protein Res. 37, 487-493;
17. (b) Lam, K.S., Salmon, S.E., Hersh, E.M., Hruby, V.J., Kazmierski, W.M. & Knapp, R. (1991) Nature (London) 354, 82-84
18. Sasaki, Y. & Coy, D.H. (1987) Peptides 8, 119-121
19. Ho, P.T., Chang, D., Zhang, T.W. & Musso, G.F. (1993) Peptide Res. 6, 10-12
20. Sakakibara, S. (1971) in Chemistry and Biochemistry of Amino Acids. Peptides and Proteins (Weinstein, B., ed.), vol. I, pp. 51-85, Marcel Dekker, New York
21. Sarin, V.K., Kent, S.B.H., Tam, J.P. & Merrifield, R.B. (1981) Anal. Biochem. 117, 147-157
22. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P.I. (1970) Anal. Biochem. 34, 595-598
23. (a) Cushman, M., Young-im, O., Copeland, T.D., Oroszlan, S. & Snyder, S.W. (1991) J Org. Chem. 56, 4161-4167;
24. (b) Sasaki, Y., Murphy, W.A., Heiman, M.L., Lance, V.A. & Coy, D.H. (1987) J. Med. Chem. 30, 1162-1166
25. (a) Frerot, E., Coste, J., Pantaloni, A., DuFour, N. & Jouin, P. (1991) Tetrahedron, 47, 259-270;
26. (b) Castro, B., Coste, J., DuFour, M.-N., & Pantaloni, A. (1989) in Peptides: Chemistry, Structure and Biology (Rivier J.E. & Marshall, G.R. eds.), pp. 885-888
27. Spatola, A.F., Saneii, H., Edwards, J.V., Bettag, A.L., Anwer, M.K., Rowell, P., Browne, P., Lahti, R., & Voigtlander, P.V. (1986) Life Sci. 38, 1243-1249
28. Sasaki, Y., Murphy, W.A., Heiman, M.L., Lance, V.A. & Coy, D.H. (1987) J Med. Chem. 30, 1162-1166
29. Spatola, A.F., Darlak, K. & Romanovskis, P. (1996) Tetrahedron Lett., 37, 591-594
30. Spatola, A.F., Crozet, Y., Romanovskis, R. & Valente, E. Peptides, Chemistry, Structure and Biology, Proceedings of the Fourteenth American Peptide Symposium, (1996) 281-283
31. Mutter, M. (1977) J. Am. Chem. Soc. 99, 8307-8314
32. Carpino, L.A. (1993) J. Am. Chem. Soc. 115, 4397-4398
33. Knorr, R., Trzeciak, A., Bannwarth, W. & Gillessen, D. (1989) Tetrahedron Lett. 30, 1927-1930
34. Erickson, B.W. & Merrifield, R.B. (1973) J. Am. Chem. Soc. 95, 3750-3756