Peptide thioacylation with high stereochemical preservation

Synthesis

Volumn , Issue 3, 1996, Pages 383-387

  Hoeg Jensen, Thomas ^a,b   Holm, Arne ^a   Sorensen, Hilmer ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NOVO NORDISK A S   (Denmark)

Author keywords

monothio acids; peptide thioamides; PyNOP; stereochemical preservation

Indexed keywords

PEPTIDE DERIVATIVE; THIOAMIDE;

ARTICLE; DRUG SYNTHESIS; MICELLAR ELECTROKINETIC CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0029971435     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4437     Document Type: Article

References (30)

1. Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.
2. Yokoyama, M.; Hasegawa, Y.; Hatanaka, H.; Kawazoe, Y.; Imamoto, T. Synthesis 1984, 827.
3. Clausen, K.; Thorsen, M.; Lawesson, S. O.; Spatola, A. F. J. Chem. Soc., Perkin Trans. 1 1984, 785.
4. Douglas, A. J.; Walker, B.; Elmore, D. T.; Murphy, R. F. Biochem. Soc. Trans. 1987, 15, 927.
5. Thorsen, M.; Yde, B.; Pedersen, U.; Clausen, K.; Lawesson, S. O. Tetrahedron 1983, 39, 3429.
6. Jensen, O. E.; Senning, A. Tetrahedron 1986, 42, 6555.
7. Hartke, K. Phosphorus, Sulfur and Silicon 1991, 58, 223.
8. Jurayj, J.; Cushman, M. Tetrahedron 1992, 48, 8601.
9. Le, H.-T.; Mayer, M.; Thoret, S.; Michelot, R. Int. J. Peptide Protein Res. 1995, 45, 138.
10. Zacharie, B.; Mantel, R.; Sauve, G.; Belleau, B. Bioorg. Med. Chem. Lett. 1993, 3, 619.
11. Zacharie, B.; Sauve, G.; Penney, C. Tetrahedron 1993, 49, 10489.
12. Hoeg-Jensen, T.; Jacobsen, M. H.; Olsen, C. E.; Holm, A. Tetrahedron Lett. 1991, 32, 7617.
13. Hoeg-Jensen, T.; Olsen, C. E.; Holm, A. J. Org. Chem. 1994, 59, 1257.
14. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
15. Yamashiro, D.; Blake, J. Int. J. Peptide Protein Res. 1981, 18, 383.
16. Hoeg-Jensen, T.; Spatola, A. F.; Holm, A., submitted (1995).
17. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201.
18. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
19. Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279.
20. Mitin, Y. V.; Zapevalova, N. P. Int. J. Peptide Protein Res. 1990, 35, 352.
21. Brillon, D. Synth. Commun. 1990, 20, 3085.
22. Michaelsen, S.; Sorensen, H. Pol. J. Food Nul. Sci. 1994, 3, 5.
23. Yamashiro, D.; Li, C. H. Int. J. Peptide Protein Res. 1988, 31, 322.
24. Nguyen, D. L.; Heitz, A.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1987, 1915.
25. Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437.
26. Yutilov, Y. M.; Ignatenko, A. G. Khim. Prom-st., Ser.: Reakt. Osobo Chist. Veshchestva 1981, 3, 27; Chem. Abstr. 1982, 96, 68773.
27. Yutilov, Y. M.; Ignatenko, A. G. Khim. Prom-st., Ser.: Reakt. Osobo Chist. Veshchestva 1981, 3, 27; Chem. Abstr. 1982, 96, 68773.
28. Mokrushina, G. A.; Azev, Y. A.; Postovskii, I. Y. Chem. Heterocycl. Compds. 1975, 880.
29. Sacher, R. M.; Alt, G. H.; Darlington, W. A. J. Agr. Food Chem. 1973, 21, 132.
30. Cheng, H. C.; Yamashiro, D. Int. J. Peptide Protein Res. 1991, 38, 70.