Total synthesis of the cyclic heptapeptide Argyrin B: A new potent inhibitor of T-cell independent antibody formation

Organic Letters

Volumn 4, Issue 5, 2002, Pages 711-714

  Ley, Steven V ^a   Prieur, Alain ^a   Heusser, Christoph ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARGYRIN B; CYCLOPEPTIDE; IMMUNOSUPPRESSIVE AGENT; INDOLE DERIVATIVE; OLIGOPEPTIDE;

ANIMAL; ANTIBODY PRODUCTION; ARTICLE; CHEMISTRY; DRUG EFFECT; HUMAN; IMMUNOLOGY; SYNTHESIS; XENOGRAFT;

ANIMALS; ANTIBODY FORMATION; HUMANS; IMMUNOSUPPRESSIVE AGENTS; INDOLES; OLIGOPEPTIDES; PEPTIDES, CYCLIC; TRANSPLANTATION, HETEROLOGOUS;

EID: 0037035008     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017184m     Document Type: Article

References (19)

1. Full details of the biological data, the isolation, and the X-ray crystal structure characterization will be reported separately.
2. Hofle, G. GBF Scientific Annual Report; Walsdorff, H.-J., Ed.; GBF: Braunschweig, 1996; p 112.
3. Revised structure and absolute configuration can be found in: Höfle, G.; Vollbrecht, L. GBF Scientific Annual Report; Walsdorff, H.-J., Ed.; GBF: Braunschweig, 2000/2001; p 99.
4. Skelly, R. R.; Munkenbeck, P.; Morisson, D. C. Infect. Immun. 1979, 23, 287.
5. Pike, B. L.; Nossal, G. J. V. J. Immunol. 1984, 132, 1687.
6. Morgan, E. L.; Weigle, W. O. 1983, 130, 1066.
7. Brinkmann, V.; Kristofic, C. J. Immunol. 1995, 154, 3078.
8. Levy, F.; Kristofic, C.; Heusser, C.; Brinkmann, V. Int. Arch. Allergy Immunol. 1997, 112, 49.
9. Sanglier, J J.; Quesniaux, V.; Fehr, T.; Hofmann, H.; Mahnke, M.; Memmert, K.; Schuler, W.; Zenke, G., Gschwind, L.; Maurer, C.; Schilling, W. J. Antibiot. 1999, 52, 466.
10. Kigoshi, H.; Yamada, S. Tetrahedron 1999, 55, 12301.
11. Lajoie, G.; Lépine, F.; Maziak, L.; Belleau, B. Tetrahedron Lett. 1983, 24, 3815.
12. Aguilar, E.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 2473.
13. Meseguer, B.; Alonso-Díaz, D.; Griebenow, N.; Herget, T.; Waldmann H. Chem. Eur. J. 2000, 6, 3943.
14. The racemic N-phenylacetyl-4-methoxy tryptophan was obtained from 4-methoxy indole (4 steps, 63% yield).
15. Okeley, N. M.; Zhu, Y.; van der Donk, W. A. Org. Lett. 2000, 2, 3603.
16. Sakai, M.; Hashimoto, K.; Shirahama, H. Heterocycles 1997, 44, 319.
17. Coste, J.; Frérot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991, 32, 1967.
18. We thank Prof. Dr. G. Höfle from the GBF, Braunschweig for an authentic sample of Argyrin B (1).
19. We note the data are remarkably similar to those of antibiotic A21459 A (Selva, E.; Gastaldo, L., Saddler, G. S., Toppo, G. Ferrari, P.; Carniti, G.; Goldstein, B. P. J. Antibiot. 1996, 49, 150.