Synthesis and X-ray crystal structure of the Dolabella auricularia peptide dolastatin 18

Journal of Organic Chemistry

Volumn 69, Issue 12, 2004, Pages 4019-4022

  Pettit, George R ^a   Hogan, Fiona ^a   Herald, Delbert L ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; AMINO ACIDS; CELLS; CONDENSATION; CRYSTAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

DOLASTATIN; TRIPEPTIDES;

POLYPEPTIDES;

CARBOXYLIC ACID; DOLAPHENINE; DOLASTATIN; DOLASTATIN 10; DOLASTATIN 18; PEPTIDE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL GROWTH; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DOLABELLA AURICULARIA; DRUG ISOLATION; GROWTH INHIBITION; HUMAN; HUMAN CELL; MOLLUSC; NONHUMAN; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; MOLLUSCA; OLIGOPEPTIDES; PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2942556917     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030358o     Document Type: Article

References (35)

1. Antineoplastic Agents. 508. For part 507, see: Pettit, R. K.; Pettit, G. R. Soil DNA Libraries for Anticancer Drug Discovery, in preparation.
2. (a) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems R. J. J. Am. Chem. Soc. 1987, 109, 6883-6885.
3. (b) Pettit, G. R. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds; Springer-Verlag: Vienna, 1997; Vol. 70, pp 1-79.
4. (c) Pettit, G. R.; Singh, S. B.; Hogan, F.; Lloyd-Williams, P.; Herald, D. L.; Burkett, D. D.; Clewlow, P. J. J. Am. Chem. Soc. 1989, 111, 5463-5465.
5. (d) Pettit, G. R.; Srirangam, J. K.; Singh, S. B.; Williams, M. D.; Herald, D. L.; Barkóczy, J. B.; Kantoci, D. K.; Hogan, F. J. Chem. Soc., Perkin Trans. 1 1996, 859-863.
6. (e) Pettit, G. R.; Grealish, M. P. J. Org. Chem. 2001, 66, 8640-8642.
7. (a) Margolin, K.; Longmate, J.; Synold, T. W.; Gandara, D. R.; Weber, J. ; Gonzalez, R.; Johansen, M. J.; Newman, R.; Baratta, T.; Doroshow, J. H. Invest. New Drugs 2001, 19, 335-340.
8. (b) Pitot, H. C.; McElroy, E. A., Jr.; Reid, J. M.; Windebank, A. J.; Sloan, J. A.; Erlichman, C.; Bagniewski, P. G.; Walker, D. L.; Rubin, J.; Goldberg, R. M.; Adjei, A. A.; Ames, M. M. Clin. Cancer Res. 1945, 5, 525-531.
9. (a) Dang, L. H.; Bettegowda, C.; Huso, D. L.; Kinzler, K. W.; Vogelstein, B. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 15155-15160.
10. (b) Turner, T.; Jackson, W. H.; Pettit, G. R.; Wells, A.; Kraft, A. S. Prostate 1998, 34, 175-181.
11. Kigoshi, H.; Itoh, T.; Ogawa, T.; Ochi, K.; Okada, M.; Suenaga, K.; Yamada, K. Tetrahedron Lett. 2001, 42, 7461-7464.
12. (a) Gerwick, W. H.; Tan, L. T.; Sitachitta, N. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; Vol. 57, pp 75-184.
13. (b) Luesch, H.; Harrigan, G. G.; Goetz, G.; Horgen, F. D. Curr. Med. Chem. 2002, 9, 1791-1806.
14. (c) Luesch, H.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H. J. Nat. Prod. 2001, 64, 907-910.
15. (d) Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H. J. Nat. Prod. 2002, 65, 16-20.
16. (e) Nogle, L. M.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 21-24.
17. (a) Pettit, G. R., Xu, J.-P.; Hogan, F.; Williams, M. D.; Doubek, D. L.; Schmidt, J. M.; Cerny, R. L.; Boyd, M. R. J. Nat. Prod. 1997, 60, 752-754.
18. (b) Pettit, G. R.; Xu, J.-P.; Hogan, F.; Cerny, R. L. Heterocycles 1998, 47, 491-496.
19. (c) Pettit, G. R.; Xu, J.-P.; Williams, M. D.; Hogan, F.; Schmidt, J. M. Bioorg. Med. Chem. Lett. 1997, 7, 827-832.
20. (d) Orjala, J.; Gerwick, W. H. J. Nat. Prod. 1996, 59, 427-430.
21. McDermott, J. R.; Benoiton, N. L. Can. J. Chem. 1973, 51, 1915-1919.
22. Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 1992, 48, 7251-7264.
23. (a) Yamada, S.; Kasai, Y.; Shioiri, T. Tetrahedron Lett. 1973, 1595-1598.
24. (b) Yamada, S.; Ikota, N.; Shioiri, T.; Tachibana, S. J. Am. Chem. Soc., 1975, 97, 7174-7175.
25. Coste, J.; Frérot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
26. Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087-2088.
27. Carpino, L. A.; Sadat-Aalaee, D.; Beyermann, M. J. Org. Chem. 1990, 55, 1673-1675.
28. (a) Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1994; pp 142-143.
29. (b) Kappeler, H.; Schwyzer, R. Helv. Chim. Acta 1960, 43, 1453-1459.
30. 1H NMR spectrum of the natural dolastatin 18 (see ref 7c) should be corrected to δ 5.44.
31. Pettit, G. R.; Lippert, J. W., III; Taylor, S. R.; Tan, R.; Williams, M. D. J. Nat. Prod. 2001, 64, 883-891.
32. XPREP-The automatic space group determination program in the SHELXTL (see ref 19).
33. North, A. C.;Phillips, D. C.; Mathews, F. S. Acta Crystallogr. 1968, A2, 351.
34. SHELXTL-PC Version 5.1, an integrated software system for the determination of crystal structures from diffraction data, Bruker Analytical X-ray Systems, Inc., Madison, WI 53719, 1997. This package includes, among others: XPREP, an automatic space group determination program; XS, the Bruker SHELXS module for the solution of X-ray crystal structures from diffraction data; XL, the Bruker SHELXL module for structure refinement; XP, the Bruker interactive graphics display module for crystal structures.
35. Flack, H. D. Acta Crystallogr. 1983, 876-881.