Fundamental Role of the Fostriecin Unsaturated Lactone and Implications for Selective Protein Phosphatase Inhibition

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 15694-15695

  Buck, Suzanne B ^a   Hardouin, Christophe ^a   Ichikawa, Satoshi ^a   Soenen, Danielle R ^a   Gauss, C M ^a   Hwang, Inkyu ^a   Swingle, Mark R ^b   Bonness, Kathy M ^b   Honkanen, Richard E ^b   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF SOUTH ALABAMA COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FOSTRIECIN; LACTONE; PHOSPHOPROTEIN PHOSPHATASE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR;

ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; STEREOCHEMISTRY;

ALKENES; AMINO ACID SEQUENCE; ENZYME INHIBITORS; LACTONES; MOLECULAR SEQUENCE DATA; PHOSPHOPROTEIN PHOSPHATASE; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 10744233991     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038672n     Document Type: Article

References (33)

1. Tunac, J. B.; Graham, B. D.; Dobson, W. E. J. Antibiot. 1983, 36, 1595.
2. Review: (a) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005.
3. For earlier reviews, see: (b) Jackson, R. C.; Fry, D. W.; Boritzki, T. J.; Roberts, B. J.; Hook, K. E.; Leopold, W. R. Adv. Enzyme Regul. 1985, 23, 193.
4. (c) De Jong, R. S.; De Vries, E. G. E.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413.
5. De Jong, R. S.; Mulder, N. H.; Uges, D. R. A.; Sleijfer, D. Th.; Hoppener, F. J. P.; Groen, H. J. M.; Willemse, P. H. B.; Van der Graaf, W. T. A.; De Vries, E. G. E. Br. J. Cancer 1999, 79, 882.
6. Boritzki, T. J.; Wolfard, T. S.; Besserer, J. A.; Jackson, R. C.; Fry, D. W. Biochem. Pharmacol. 1988, 37, 4063.
7. (a) Cheng, A.; Balczon, R.; Zuo, Z.; Koons, J. S.; Walsh, A. H.; Honkanen, R. E. Cancer Res. 1998, 58, 3611.
8. (b) Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230.
9. (c) Connor, J. H.; Kleeman, T.; Barik, S.; Honkanen, R. E.; Shenolikar, S. J. Biol. Chem. 1999, 274, 22366.
10. Roberge, M.; Tudan, C.; Hung, S. M.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115.
11. Hastie, C. J.; Cohen, P. T. W. FEBS Lett. 1998, 431, 357.
12. Honkanson, G. C.; French, J. C. J. Org. Chem. 1985, 50, 462.
13. Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748.
14. (a) Boger, D. L.; Ichikawa, S.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161.
15. (b) Additional reports: Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667.
16. (c) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969.
17. (d) Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. Chem. Commun. 2002, 742.
18. (e) Esumi, T.; Okamoto, N.; Hatakeyama, S. Chem. Commun. 2002, 3042.
19. (f) Kiyotsuka, Y.; Igarashi, J.; Kobayashi, Y. Tetrahedron Lett. 2002, 43, 2725.
20. (g) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615.
21. (h) Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733.
22. (i) Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. J. Am. Chem. Soc. 2003, 125, 8238.
23. Review: Sheppeck, J. E., II; Gauss, C.-M.; Chamberlin, A. R. Bioorg. Med. Chem. 1997, 5, 1739.
24. Gauss, C.-M.; Sheppeck, J. E., II; Nairn, A. C.; Chamberlin, R. Bioorg. Med. Chem. 1997, 5, 1751.
25. Goldberg, J.; Huang, H.-B.; Kwon, Y.-G.; Greengard, P.; Nairn, A. C.; Kuriyan, J. Nature 1995, 376, 745.
26. Egloff, M.-P.; Cohen, P. T. W.; Reinemer, P.; Barford, D. J. Mol. Biol. 1995, 254, 942.
27. Compound 8 provides a readily reversible adduct, whereas hydrolysis to 10 would be expected to provide a more stable, less reversible adduct.
28. Evans, D. R. H.; Simon, J. A. FEBS Lett. 2001, 498, 110.
29. The structure of 5, whose lack of activity has been disclosed,4 was incorrectly assigned as the monophosphate ester8 in earlier studies.
30. 50). Thus, the C18 alcohol is known not to contribute to the properties of fostriecin,1-4 suggesting that the difference observed between 4 and 5 can be attributed to C11 O-acylation.
31. rhPP1α was expressed in E. coli with the pKK-223-3 vector (accession number M77749) and purified essentially as described: Zhang, L.; Lee, E. Y. Biochemistry 1997, 36, 8209.
32. (a) Honkanen, R. E.; Zwiller, J.; Moore, R. E.; Daily, S. L.; Khatra, B. S.; Dukelow, M.; Boynton, A. L. J. Biol. Chem. 1990, 265, 19401.
33. (b) Huang, X.; Swingle, M. R.; Honkanen, R. E. Methods Enzymol. 2000, 315, 579.