Sulfahydantoins as tripeptide constraints: Synthesis and structure of chiral substituted 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides

European Journal of Organic Chemistry

Volumn , Issue 9, 1999, Pages 2275-2283

  Boudjabi, Sihem ^a   Dewynter, Georges ^a   Voyer, Normand ^b   Toupet, Loïc ^c   Montero, Jean Louis ^a  

^a UNIV MONTPELLIER   (France)

^b UNIVERSITÉ LAVAL   (Canada)

^c UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Asymmetric synthesis; Peptides

Indexed keywords

1,2,5 THIADIAZOLIDINE 1,1 DIOXIDE DERIVATIVE; HYDANTOIN DERIVATIVE; POLYPEPTIDE; TRIPEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0032848551     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2275::aid-ejoc2275>3.0.co;2-p     Document Type: Article

References (39)

1. P. Rizo, L. M. Gierasch, Annu. Rev. Biochem. 1992, 61, 387-418.
2. A. Giannis, T. Kolter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
3. [3a] C.-H. Lee, J. D. Korp, H. Kohn, J. Org. Chem. 1989, 54, 3077-3083.
4. [3b] C.-H. Lee, H. Kohn, J. Org. Chem. 1990, 55, 6098-6104.
5. [3c] N. Aouf, G. Dewynter, J.-L. Montero, Tetrahedron Lett. 1991, 32, 6546-6547.
6. [3d] S. K. Danek, D. P. Kelly, P. J. Steel, J. Org. Chem. 1991, 56, 2031-2039.
7. [3e] C.-H. Lee, J. S. Song, Y.-H. Lee, W. S. Choi, B. Y. Chung, Bull. Korean Chem. Soc. 1993, 14, 762-764.
8. [3f] G. Dewynter, N. Aouf, M. Criton, J.-L. Montero, Tetrahedron 1993, 49, 65-76.
9. [4a] G.-A. Hanewacker, Z. Mester, B. Unterhalt, Arch. Pharm (Weinheim), 1993, 8, 497-498.
10. [4b] C.-H. Lee, H. Kohn, J. Pharm. Sci. 1990, 79, 716-718.
11. G. W. Muller, G. E. Dubois, J. Org. Chem. 1989, 54, 4471-4472.
12. G. Dewynter, N. Aouf, Z. Regainia, J.-L. Montero, Tetrahedron 1996, 52, 993-1004.
13. [7a] W. C. Groutas, R. Kuang, R. Venkataraman, J. B. Epp, S. Ruan, O. Prakask, Biochemistry 1997, 36, 4737-4750.
14. [7b] R. Kuang, R. Venkataraman, S. Ruan, W. C. Groutas, Biorg. Med. Chem. Lett. 1998, 8, 539-544.
15. [7c] W. C. Groutas, R. Kuang, S. Ruan, J. B. Epp, R. Venkataraman, T. M. Truong, Biorg. Med. Chem. 1998, 6, 661-671.
16. S. Paik, E. H. White, Tetrahedron 1996, 52, 5303-5318.
17. G. Dewynter, S. Ubaldi, N. Voyer, L. Toupet, Tetrahedron Lett. 1998, 39, 7435-7438.
18. M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 95, 1689-1708.
19. [11a] O. Mitsunobu, Synthesis 1981, 1.
20. [11b] D. L. Hughes, Organic Reactions 1992, 42, 335.
21. [11c] S. Mignani, D. Damour, A. Doble, R. Labaudiniere, J.-L. Malleron, O. Piot, C. Gueremy, Bioorg. Med. Chem. Lett. 1993, 10, 1913-1918.
22. G. C. Levy, R. L. Lichter, Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy; 1979 Wiley-Interscience. New York.
23. Crystallographic date (excluding structure factors) for the structure(s) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-114219. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int. code + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
24. [14a] K. H. Ahn, D. J. Yoo, J. S Kim, Tetrahedron Lett. 1992, 44, 6661-6664.
25. [14b] A. Herrero, C. Ochoa, J. Atienza, J. A. Escario, A. Gomez-Barrio, A. R Martinez-Fernandez, Arch. Pharm. (Weinheim) 1992, 325, 509-514.
26. [15a] W. Oppolzer, C. Chapuis, G. Bernadinelli, Helv. Chim. Acta 1984, 67, 1397-1404.
27. [15b] G. Bernadinelli, W. Oppolzer, C. D. Dupuis, Acta Cryst., Sect. C 1986, 42, 1460-1461.
28. [15c] G. Bernadinelli, W. Oppolzer, P. Schneider, Acta Cryst., Sect. C 1987, 43, 1000.
29. [15d] W. Oppolzer, S. Poli, C. Starkemann, G. Bernadinelli, Tetrahedron Lett. 1988, 29, 3559-3562.
30. [16a] P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
31. [16b] H. N. Wasserman, W. T. Han, Tetrahedron Lett. 1984, 25, 3747-3750.
32. [17a] L. J. Fitzpatrick, R. A. Rivero, Tetrahedron Lett. 1997, 38, 7479-7482.
33. [17b] M. M. Sim, A. Ganesan, J. Org. Chem. 1997, 62, 3230-3235.
34. [17c] S. Hanessian, R.-Y. Yang, Tetrahedron Lett. 1996, 37, 5835-5838.
35. M. A. Navia, B. M. McKeever, J. P. Springer, T. Y. Lin, H.R. Williams, E. M. Fluder, C. P. Dorn, K. Hoogsteen, Proc. Natl. Acad. Sci. USA 1989, 1, 7-11.
36. International Tables for X-ray Crystallography, vol. IV, Birmingham; Kynoch Press (present distributor D. Reidel, Dordrecht), 1974.
37. C. K. Fair, MolEN, An Internactive System for Crystal Structure Analysis, Enraf-Nonius, Delft, The Netherlands, 1990.
38. [21a] G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473.
39. [21b] G. M. Sheldrick, T. R. Schneider, "SHELXL: High-Resolution Refinement" in Methods in Enzymology, vol. 277 (Macromolecular Crystallography, part B) (Eds.: C. W. Carter, R. M. Sweet) 1997, p. 319-343.