Synthesis of endothiopeptides and their cyclization to 1,3-thiazol- 5(4H)-imines

Helvetica Chimica Acta

Volumn 82, Issue 11, 1999, Pages 1899-1915

  Lehmann, Jürg ^a,b   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032701312     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19991110)82:11<1899::AID-HLCA1899>3.0.CO;2-M     Document Type: Article

References (31)

1. A. F. Spatola, in 'Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins', Ed. B. Weinstein, Marcel Dekker, New York, 1983, 7, Chapter 5, p. 267.
2. J. Lehmann, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 888.
3. J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1999, 55, 5359.
4. J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721.
5. K. Clausen, M. Thorsen, S.-O. Lawesson, Tetrahedron 1981, 37, 3635.
6. M. Thorsen, B. Yde, U. Pedersen, K. Clausen, S.-O. Lawesson, Tetrahedron 1983, 39, 3429.
7. D. Seebach, S. Y. Ko, H. Kessler, M. Köck, M. Reggelin, P. Schmider, M. D. Walkinshaw, J. J. Bölsterli, D. Bevec, Helv. Chim. Acta 1991, 74, 1953.
8. J. Jurayj, M. Cushman, Tetrahedron 1992, 48, 8601.
9. D. T. Elmore, D. J. S. Guthrie, G. Kay, C. H. Williams, J. Chem. Soc., Perkin Trans. 1 1988, 1051.
10. H.-T. Le, M. Mayer, S. Thoret, R. Michelot, Int. J. Peptide Protein Res. 1995, 45, 138.
11. K. Hartke, S. Barrmeyer, J. Prakt. Chem. 1996, 338, 251.
12. T. Høeg-Jensen, A. F. Spatola, A. Holm, Int. J. Pept. Protein Res. 1996, 47, 190.
13. T. Høeg-Jensen, C. E. Olsen, A. Holm, J. Org. Chem. 1994, 59, 1257.
14. B. Zacharie, G. Sauvé, C. Penney, Tetrahedron 1993, 49, 10489.
15. M. A. Shalaby, C. W. Grote, H. Rapoport, J. Org. Chem. 1996, 61, 9045.
16. C. T. Brain, A. Hallet, S. Y. Ko, J. Org. Chem. 1997, 62, 3808.
17. N. Ramakrishnan, P. Balaram, Acc. Chem. Res. 1981, 14, 356.
18. G. Jung, H. Brückner, H. Schmitt, in 'Structure and Activity of Natural Peptides', Ed. W. Voelter and G. Weitzel, de Gruyter, Berlin, 1981, p. 75.
19. I. L. Karle, J. L. Flippen-Anderson, K. Uma, P. Balaram, Biochemistry 1989, 28, 6696.
20. K.-H. Altmann, E. Altmann, M. Mutter, Helv. Chim. Acta 1992, 75, 1198.
21. C. Toniolo, M. Crisma, F. Formaggio, G. Valle, G. Cavicchioni, G. Precigoux, A. Aubry, J. Kamphuis, Biopolymers 1993, 33, 1061.
22. A. Aubry, D. Bayeul, H. Bruckner, N. Schiemann, E. Benedetti, J. Peptide Science 1998, 4, 502.
23. R. Gessmann, P. Benos, H. Brückner, M. Kokkinidis, J. Peptide Science 1999, 5, 83.
24. M. Tanaka, N. Imawaka, M. Kurihara, H. Suemune, Helv. Chim. Acta 1999, 82, 494.
25. H. Heimgartner, Angew. Chem., Int. Ed. 1991, 30, 238.
26. R. Luykx, C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 527.
27. C. B. Bucher, H. Heimgarlner, Helv. Chim. Acta 1996, 79, 1903.
28. C. Strässler, A. Linden, H. Heimgartner, Helv. Chim. Acta. 1997, 80, 1528.
29. I. L. Karle, M. Sukumar, P. Balaram, Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 9284.
30. J. Shi, A. Linden, H. Heimgartner, Helv. Chim. Acta 1994, 77, 1903.
31. G. Mlostoń, J. Romański, A. Linden, H. Heimgartner, Polish. J. Chem. 1996, 70, 880.