Molecular diversity of peptidomimetics: Approaches to the solid-phase synthesis of peptidosulfonamides

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 5, 1996, Pages 667-672

  De Bont, Dries B A ^a   Moree, Wilna J ^a,b   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Biopolymer mimetics; Molecular diversity; Peptidosulfonamides; Solid phase

Indexed keywords

SULFONAMIDE;

CONFERENCE PAPER; DRUG SYNTHESIS; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0029953649     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00061-2     Document Type: Conference Paper

References (32)

1. Liskamp, R. M. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 633.
2. Simon, R. J.; Kania, R. S.; Zuckermann, R. N.; Huebner, V. D.; Jewell, D. A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C. K.; Spellmeyer, D. C.; Tan, R.; Frankel, A. D.; Santi, D. V.; Cohen, F. E.; Bartlett, P. A. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 9367.
3. Kessler, H. Angew. Chem. Int. Ed. Engl. 1993, 32, 543.
4. Cho, C. Y.; Moran, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacobs, J. W.; Schultz, P. G. Science 1993, 261, 1303.
5. (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055.
6. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 2586.
7. (c) Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907.
8. (d) Barré, C.; Le Grel, P.; Robert, A.; Baudy-Floc'h, M. J. Chem. Soc., Chem. Commun. 1994, 607.
9. Moran, E. J.; Wilson, T. E.; Cho, C. Y.; Cherry, S. R.; Schultz, P. G. Biopolymers 1995, 37, 213. Sommerfield, T.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 553.
10. Moran, E. J.; Wilson, T. E.; Cho, C. Y.; Cherry, S. R.; Schultz, P. G. Biopolymers 1995, 37, 213. Sommerfield, T.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 553.
11. (a) Moree, W. J.; van der Marel, G. A.; Liskamp, R. M. J. Tetrahedron Lett. 1991, 32, 409.
12. (b) Moree, W. J.; van der Marel, G. A.; Liskamp, R. M. J. Tetrahedron Lett. 1992, 33, 6389.
13. (c) Moree, W. J.; van der Marel, G. A.; Liskamp, R. M. J. Tetrahedron 1993, 49, 1133.
14. (d) Moree, W. J.; Schouten, A.; Kroon, J.; Liskamp, R. M. J. Int J. Pept. Prot. Res. 1995, 45, 501.
15. (e) Moree, W. J.; van der Marel, G. A.; Liskamp, R. M. J. J. Org. Chem . 1995, 60, 5157.
16. (f) Gennari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 2067.
17. (g) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. ibid. 1995, 34, 1763.
18. (h) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
19. Zuckermann, R. N.; Martin, E. J.; Spellmeyer, D. C.; Stauber, G. B.; Shoemaker, K. R.; Kerr, J. M.; Figliozzi, G. M.; Goff, D. A.; Siani, M. A.; Simon, R. J.; Banville, S. C.; Brown, E. G.; Wang, L.; Richter, L. S.; Moos, W. H. J. Med. Chem. 1994, 37, 2678.
20. Gisin, B. F. Helv. Chim. Acta 1973, 56, 1476.
21. Stewart, J. F.; Young, J. D. Solid Phase Peptide Synthesis, Pierce Chemical: Rockford, Illinois, 1984; p 91.
22. (a) Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc. Chem., Chem. Commun. 1987, 1625.
23. (b) Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
24. Guertin, K. R.; Kende, A. S. Tetrahedron Lett. 1993, 34, 5369.
25. Sieber, P. Tetrahedron Lett. 1987, 28, 6147.
26. 4, thereby possibly preventing oxidation of the sulfinamides to the corresponding sulfonamides. Instead of benzoylchloride, the more commonly used acetic anhydride can be used for capping. However, benzoylchloride was used to discriminate between acylation as the result of capping and acylation by acetyl chloride, which was liberated during the preparation of the sulfinylchloride.
27. Kaldor, S. W.; Hammond, M. Tetrahedron Lett. 1991, 32, 5043; Priebe, W.; Grynkiewicz, G. Tetrahedron Lett. 1991, 32, 7353
28. Kaldor, S. W.; Hammond, M. Tetrahedron Lett. 1991, 32, 5043; Priebe, W.; Grynkiewicz, G. Tetrahedron Lett. 1991, 32, 7353
29. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 45. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 47
30. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 45. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 47
31. Trost, B. M.; Braslau, R. J. Org. Chem. 1988, 53, 532.
32. Arx, E. V.; Faupel, M.; Brugger, M. J. J. Chromatogr. 1976, 120, 224.