Antineoplastic agents. 590. X-ray crystal structure of dolastatin 16 and syntheses of the dolamethylleuine and dolaphenvaline units

Journal of Natural Products

Volumn 74, Issue 5, 2011, Pages 1003-1008

  Pettit, George R ^a   Smith, Thomas H ^a   Xu, Jun Ping ^a   Herald, Delbert L ^a   Flahive, Erik J ^a   Anderson, Collin R ^a   Belcher, Paul E ^a   Knight, John C ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DOLAMETHYLLEUINE; DOLAPHENVALINE; DOLASTATIN; DOLASTATIN 16; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; MOUSE; NONHUMAN; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; DEPSIPEPTIDES; MOLECULAR STRUCTURE;

EID: 79957862110     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100877h     Document Type: Article

References (30)

1. For contribution 589 consult: Prokopiou, E. M.; Cooper, P. A.; Pettit, G. R.; Bibby, M. C.; Shnyder, S. D. Mol. Med. Rep. 2010, 3, 309-313.
2. (a) Pettit, G. R. In International Oncology Updates: Marine anticancer compounds in the era of targeted therapies; Chabner, B.; Cortés-Funes, H., Eds.; Permanyer Publications: Barcelona, 2009.
3. (b) Kingston, D. G. I. J. Nat. Prod. 2009, 72, 507-515.
4. (c) Singh, R.; Sharma, M.; Joshi, P.; Rawat, D. S. Anti-Cancer Agents Med. Chem. 2008, 8, 603-617.
5. (d) Pettit, G. R. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Kirby, G. W.; Moore, R. E.; Steglich, W.; Tamm, C., Eds.; Springer: Vienna, 1997; Vol. 70, pp 1-79.
6. (a) Woyke, T.; Roberson, R. W.; Pettit, G. R.; Winkelmann, G.; Pettit, R. K. Antimicrob. Agents Chemother. 2002, 46, 3802-3808.
7. (b) Woyke, T.; Berens, M. E.; Hoelzinger, D. B.; Pettit, G. R.; Winkelmann, G.; Pettit, R. K Antimicrob. Agents Chemother. 2004, 48, 561-567.
8. (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.
9. (b) Paterson, I.; Findlay, A. D. Aust. J. Chem. 2009, 62, 624-638.
10. (c) Paterson, I.; Findlay, A. D. Pure Appl. Chem. 2008, 80, 1773-1782.
11. (a) Luesch, H.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H. J. Nat. Prod. 2001, 64, 907-910.
12. (b) Harrigan, G. G.; Yoshida, W. Y.; Moore, R. E.; Nagle, D. G.; Park, P. U.; Biggs, J.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H.; Valeriote, F. A. J. Nat. Prod. 1998, 61, 1221-1225.
13. (c) Nogle, L. M.; Williamson, R. T.; Gerwick, W. H. J. Nat. Prod. 2001, 64, 716-719.
14. (d) Gunasekera, S. P.; Miller, M. W.; Kwan, J. C.; Luesch, H.; Paul, V. J. J. Nat. Prod. 2010, 73, 459-462.
15. (e) Adams, B.; Pörzgen, P.; Pittman, E.; Yoshida, W. Y.; Westenburg, H. E.; Horgen, F. D. J. Nat. Prod. 2008, 71, 750-754.
16. (f) Taori, K.; Liu, Y.; Paul, V. J.; Luesch, H. ChemBioChem 2009, 10, 1634-1639.
17. (g) Nogle, L. M.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 21-24.
18. Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217-1228.
19. Hirai, Y.; Yokota, K.; Momose, T. Heterocycles 1994, 39, 603-612.
20. Seebach, D.; Estermann, H. Tetrahedron Lett. 1987, 28, 3103-3106.
21. Mehta, A.; Jaouhari, R.; Benson, T. J.; Douglas, K. T. Tetrahedron Lett. 1992, 33, 5441-5444.
22. Kimura, J.; Takada, Y.; Inayoshi, T.; Nakao, Y.; Goetz, G.; Yoshida, W. Y.; Scheuer, P. J. J. Org. Chem. 2002, 67, 1760-1767.
23. Mues, H.; Kazmaier, U. Synthesis 2001, 487-498.
24. Kazmaier, U.; Mues, H.; Krebs, A. Chem. - Eur. J. 2002, 8, 1850-1855.
25. Duboudin, J. G.; Jousseaume, B.; Saux, A. J. Organomet. Chem. 1979, 168, 1-11.
26. Lau, C. K.; Dufresne, C.; Belanger, P. C.; Piétré, S.; Scheigetz, J. J. Org. Chem. 1986, 51, 3038-3043.
27. Taber, D. F.; Gerstenhaber, D. A.; Zhao, X. Tetrahedron Lett. 2006, 47, 3065-3066.
28. Keck, G. E.; Giles, R. L.; Cee, V. J.; Wager, C. A.; Yu, T.; Kraft, M. B. J. Org. Chem. 2008, 73, 9675-9691.
29. CCDC 801992 (1), 801990 (8), and 801991 (20) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
30. Pettit, G. R.; Knight, J. C.; Herald, D. L.; Pettit, R. K.; Hogan, F.; Mukku, V. J. R. V.; Hamblin, J. S.; Dodson, M. J., II; Chapuis, J.-C. J. Nat. Prod. 2009, 72, 366-371.