Total synthesis of the potent proteasome inhibitor epoxomicin: A useful tool for understanding proteasome biology

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 15, 1999, Pages 2283-2288

  Sin, Ny ^a   Kyung, Bo Kim ^a   Elofsson, Mikael ^a   Meng, Lihao ^a   Auth, Hak ^a   Kwok, Benjamin H B ^a   Crews, Craig M ^a,b  

^a YALE UNIVERSITY   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; EPOXOMICIN; PACLITAXEL; PROTEASOME INHIBITOR; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINCRISTINE SULFATE;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG CONFORMATION; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME INHIBITION; TARGET CELL;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIBIOTICS, ANTINEOPLASTIC; BIOTINYLATION; CYSTEINE ENDOPEPTIDASES; ENZYME INHIBITORS; MICE; MULTIENZYME COMPLEXES; OLIGOPEPTIDES; PROTEASOME ENDOPEPTIDASE COMPLEX; RECEPTORS, DRUG; TUMOR CELLS, CULTURED;

UNCULTURED ACTINOMYCETE;

EID: 0033517032     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00376-5     Document Type: Article

References (25)

1. Schreiber, S. L. Bioorg. Med. Chem. 1998, 6, 1127.
2. Liu, J.; Farmer, J. D. J.; Lane, W. S.; Friedman, J.; Weissman, I.; Schreiber, S. L. Cell 1991, 66, 807.
3. Brown, E. J.; Albers, M. W.; Shin, T. B.; Ichikawa, K.; Keith, C. T.; Lane, W. S.; Schreiber, S. L. Nature 1994, 369, 756.
4. Sin, N.; Meng, L.; Wang, M. Q.; Wen, J. J.; Bornmann, W. G.; Crews, C. M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 6099.
5. Meng, L.; Kwok, B. H. B.; Sin, N.; Crews, C. M. Cancer Res. 1999, 59, 2798.
6. Hanada, M.; Sugawara, K.; Kaneta, K.; Toda, S.; Nishiyama, Y.; Tomita, K.; Yamamoto, H.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1746.
7. Sugawara, K.; Hatori, M.; Nishiyama, Y.; Tomita, K.; Kamei, H.; Konishi, M.; Oki, T. J. Antibiot. 1990, 43, 8.
8. Tsuchiya, K.; Kobayashi, S.; Nishikiori, T.; Nakagawa, T.; Tatsuta, K. J. Antibiot. 1997, 50, 261.
9. Spaltenstein, A.; Leban, J. J.; Huang, J. J.; Reinhardt, K. R.; Viveros, O. H.; Sigafoos, J.; Crouch, R. Tetrahedron Lett. 1996, 37, 1343.
10. Hilt, W.; Wolf, D. H. Trends Biochem Sci 1996, 21, 96.
11. Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.;Schreiber, S. L. Science 1995, 268, 726.
12. Lee, D.H.; Goldberg, A. L. Trends Cell Biol 1998, 8, 397.
13. Meng, L.; Mohan, R.; Kwok, B. H. B.; Elofsson, M.; Sin, N.; Crews, C. M. Proc. Natl. Acad. Sci. U.S.A. 1999, in press.
14. Schmidt, U.; Schmidt, J. J. Chem. Soc. Chem. Commun. 1992, 529.
15. Schmidt, U.; Schmidt, J. Synthesis 1994, 300.
16. Hoshi, H.; Ohnuma, T.; Aburaki, S.; Konishi, M.; Oki, T. Tetrahedron Lett. 1993, 34, 1047.
17. Sin, N.; Meng, L.; Auth, H.; Crews, C. M. Bioorg. Med. Chem. 1998, 6, 1209.
18. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
19. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc. Chem. Commun. 1994, 201.
20. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
21. Spencer, J. R.; Antonenko, V. V.; Delaet, N. G.; Goodman, M. Int. J. Pept. Protein Res. 1992, 40, 282.
22. Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161.
23. Grant, G. A. E. Synthetic Peptides: A User's Guide; W. H. Freeman and Company: New York, 1992.
24. 3H]-epoxomicin 14 for 15 min at rt before SDS-PAGE and transfer to PVDF membrane, which was exposed to Kodak Biomax X-ray film for 21 days.
25. Roush, W. R.; Gonzalez, F. V.; McKerrow, J. H.; Hansell, E. Bioorg. Med. Chem. Lett. 1998, 8, 2809.