Biological and pharmacokinetic studies with β-peptides

Chimia

Volumn 52, Issue 12, 1998, Pages 734-739

  Seebach, Dieter ^a   Abele, Stefan ^a   Schreiber, Jürg V ^a   Martinoni, Bruno ^a   Nussbaum, Alexander K ^b   Schild, Hansjörg ^b   Schulz, Henk ^a   Hennecke, Hauke ^a   Woessner, Ralph ^c   Bitsch, Francis ^c  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000932043     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. Part of the projected Ph.D. theses of S.A. and J.V.S, ETH-Zürich.
2. C.N. Drey, in 'The Chemistry and Biochemistry of Amino Acids', Ed. B. Weinstein, Dekker, New York, 1976, Chapt. 4, pp. 241-299.
3. C.N. Drey, in The Chemistry and Biochemistry of Amino Acids', Ed. G.C. Barrett, Chapman & Hall, London, 1984, pp. 25-54.
4. G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 117
5. C.A. Bewley, D.J. Faulkner, Angew. Chem. 1998, 110, 2280.
6. T. Yasumoto, M. Satake, Chimia 1998, 52, 63.
7. O.W. Griffith, Ann. Rev. Biochem. 1986, 55, 855.
8. C.H. Chang, M.D. Ballinger, G.H. Reed, P.A. Frey, Biochemistry 1996, 35, 11084; K.D. Walker, H.G. Floss, J. Am. Chem. Soc. 1998, 120, 5333.
9. C.H. Chang, M.D. Ballinger, G.H. Reed, P.A. Frey, Biochemistry 1996, 35, 11084; K.D. Walker, H.G. Floss, J. Am. Chem. Soc. 1998, 120, 5333.
10. E. Abderhalden, F. Reich, Fermentforschung 1928, 10, 173.
11. E. Abderhalden, R. Fleischmann, Fermentforschung 1928, 10, 195.
12. M. Rodriguez, P. Fulcrand, J. Laur, A. Aumelas, J.P. Bali, J. Martinez, J. Med. Chem. 1989, 32, 522.
13. M. Llinares, C. Devin, J. Azay, G. Berge, J.A. Fehrentz, J. Martinez, Eur. J. Med. Chem. 1997, 32, 767.
14. Y. Hayashi, J. Katada, T. Harada, A. Tachiki, K. Iijima, Y. Takiguchi, M. Muramatsu, H. Miyazaki, T. Asari, T. Okazaki, Y. Sato, E. Yasuda, M. Yano, I. Uno, I. Ojima, J. Med. Chem. 1998, 41, 2345.
15. D. Seebach, M. Overhand, F.N.M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913.
16. D. Seebach, P.E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta 1996, 79, 2043.
17. D. Seebach, J.L. Matthews, J. Chem. Soc., Chem. Commun. 1997, 21, 2015.
18. D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J.L. Matthews, J.V. Schreiber, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1998, 81, 932.
19. a) D.H. Appella, L.A. Christianson, I.L. Karle, D.R. Powell, S.H. Gellman, J. Am. Chem. Soc. 1996, 118, 13071;
20. b) D. H. Appella, L. A. Christianson, D.A. Klein, D.R. Powell, X. Huang, J.J. Barchi, Jr., S.H. Gellman, Nature (London) 1997, 387, 381.
21. D. Seebach, S. Abele, hitherto unpublished results, ETH-Zürich, 1997.
22. S. Krauthäuser, L.A. Christianson, D.R. Powell, S.H. Gellman, J. Am. Chem. Soc. 1997, 119, 11719.
23. T. Hintermann, D. Seebach, Chimia 1997, 51, 244.
24. a) G. Guichard, D. Seebach, Chimia 1997, 51, 315;
25. b) G. Guichard, S. Abele, D. Seebach, Helv. Chim. Acta 1998, 81, 187.
26. S. Abele, G. Guichard, D. Seebach, Helv. Chim. Acta 1998, 81, in press.
27. For the syntheses of the α-peptides, see Exper. Part.
28. T. Hintermann, D. Seebach, Synlett 1997, 437.
29. L. Kuehn, B. Dahlmann, F. Gauthier, H.P. Neubauer, Biochim. Biophys. Acta 1989, 991, 263.
30. K. Tanaka, T. Yoshimura, A. Ichihara, J. Biochem. (Tokyo) 1989, 106, 495.
31. The β-amino acids were synthesized by our standard method (using the Arndt-Eistert procedure [14][29][30])andacetylated with acetic anhydride. The β-peptides 9 and 10 and the 'mixed' peptides 11 and 12 were prepared by coupling in solution [31].
32. J. Podlech, D. Seebach, Liebigs Ann. 1995, 1217.
33. J.L. Matthews, C. Braun, C. Guibourdenche, M. Overhand, D. Seebach, in 'Enantioselective Synthesis of β-Amino Acids', Ed. E. Juaristi, Wiley-VCH, Weinheim and New York, 1997, Chapt. 5, pp. 105-126.
34. D. Seebach, J. Schreiber, hitherto unpublished results, ETH-ZU7die;rich, 1998.
35. J. Sambrook, E.F. Fritsch, T. Maniatis, in 'Molecular cloning: a laboratory manual', 2nd edn., Cold Spring Harbor Laboratory Press, 1989, Cold Spring Harbor NY.
36. This is reminescent of the enzymatic cleavage experiments [21]: a β-tripeptide with an α-amino acid at the N-terminus was cleaved by leucine aminopeptidase.
37. D. Seebach, D. Rigo, unpublished results, ETH-Zürich, 1996.
38. M.F. Powell, Ann. Rep. Med. Chem. 1993, 28, 285.
39. Thus, angiotensin II, an eight-residue peptide, has a half-life of less than 1 min (iv. administration).
40. J.-L. Fauchère, C. Thurieau, Adv. Drug Res. 1992, 23, 127.
41. 2O-insoluble 18.
42. S. Beil, H. Kehrli, P. James, W. Staudenmann, A.M. Cook, T. Leisinger, M.A. Kertesz, Eur. J. Biochem. 1995, 229, 385.
43. a) H.-J. Busse, T. El-Banna, G. Auling, Appl. Environ. Microbiol. 1989, 55, 1578;
44. b) D. Zürrer, A.M. Cook, T. Leisinger, ibid. 1987, 53, 1459.