Trichodiene synthase: Synthesis and inhibition kinetics of 12-fluoro-farnesylphosphonophosphate for sesquiterpene cyclases

Journal of the Chinese Chemical Society

Volumn 53, Issue 5, 2006, Pages 1161-1172

  Chen, Yi Lin ^a   Chiu, Hsien Tai ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

Biosynthesis; Enzyme inhibitors; Enzyme kinetics; Sesquiterpene cyclases; Terpenes

Indexed keywords

EID: 34548551501     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200600154     Document Type: Article

References (76)

1. (a) Greenhagen, B.; Chappell, J. Proc. Natl. Acad. Sci. USA. 2001, 98, 13479-13481.
2. (b) Chappell, J. Annu. Rev. Plant. Physiol. Plant. Mol. Biol. 1995, 46, 521-547.
3. (a) Cane, D. E. Comprehensive Natural Products Chemistry: Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2, Elsevier: Oxford, U.K., 1999.
4. (b) Cane, D. E. In Biosynthesis of Isoprenoid Compounds; Porter, J. W. & Spurgen, S. L., Eds.; John Wiley: New York, 1981.
5. (a) Jou, S.-J.; Chen, C.-H.; Guh, J.-H.; Lee, C.-N.; Lee, S.-S. J. Chin. Chem. Soc. 2004, 51, 827-834.
6. (b) Zhang, Y.-H.; Cheng, J.-K.; Yang, L.; Cheng, D.-L. J. Chin. Chem. Soc. 2002, 49, 117-124.
7. Glasby, J. S. Encyclopedia of Terpenoids; Wiley: Chichester, 1982.
8. (a) Gao, K.; Yang, L.; Jia, Z.-J. J. Chin. Chem. Soc. 1999, 46, 619-622.
9. (b) Kuo, Y.-H.; Lee, S.-M.; Lai, J.-S. J. Chin. Chem. Soc. 2000, 47, 241-246.
10. Buckingham, J. C. Dictionary of Natural Products on CD-ROM; version 6.1, Chapman and Hall: London, U.K., 1998.
11. Papahadjoupoulos, D.; Cowden, M.; Kimelberg, H. Biochim. Biophys. Acta. 1973, 330, 8-26.
12. (a) Cane, D. E. Chem. Rev. 1990, 90, 1089-1103.
13. (b) Jong, J.-R.; Wu, C.-L. J. Chin. Chem. Soc. 2000, 47, 359-362.
14. (c) Liu, X.; Wu, Q.-X.; Shi, Y.-P. J. Chin. Chem. Soc. 2005, 52, 369-374.
15. Lesburg, C. A.; Caruthers, J. M.; Paschall, C. M.; Christianson, D. W. Curr. Opin. Struct. Biol. 1998, 8, 695-703.
16. Rising, K. A.; Starks, C. M.; Noel, J. P.; Chappell, J. J. Am. Chem. Soc. 2000, 118, 10037-10040.
17. Cane, D. E.; Xue, Q.; Van Epp, J.; Tsantrizos, Y. S. J. Am. Chem. Soc. 1996, 118, 8499-8500.
18. Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. Proc. Natl. Acad. Sci. USA. 2001, 98, 24, 13543-13548.
19. Caruthers, J. M.; Kang, I.; Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. J. Biol. Chem. 2000, 275, 25533-25539.
20. Starks, C. M.; Back, K.; Chappell, J.; Noel, J. P. Science 1997, 277, 1815-1820.
21. Lesburg, C. A.; Zhai, G.; Cane, D. E.; Christianson, D. W. Sciene 1997, 277, 1820-1824.
22. Pandit, J.; Danley, D. E.; Schulte, G. K.; Mazzalupo, S.; Pauly, T. A.; Hayward, C. M.; Humanaka, E. S.; Thompson, J. F.; Harwood, H. J. J. Biol. Chem. 2000, 275, 30610-30617.
23. Tarshis, L. C.; Yan, M.; Poulter, C. D.; Sacchettini, J. C. Biochemistry 1994, 33, 10871-10877.
24. Ueno, Y. In Trichothecenes: Chemical, Biological and Toxicological Aspects; Kodansha Ltd: Japan, 1983.
25. (a) Hohn, T. M.; Beremand, M. N. Gene 1989, 79, 131-138.
26. (b) Hohn, T. M.; Plattner, R. D. Arch. Biochem. Biophys. 1989, 275, 92-97.
27. (a) Cane, D. E.; Wu, Z.; Oliver, J. S.; Hohn, T. M. Arch. Biochem. Biophys. 1993, 300, 416-422.
28. (b) Cane, D. E.; Shim, J. H.; Xue, Q.; Fitzsimons, B. C. Biochemistry 1995, 34, 2480-2488.
29. (a) Cane, D. E.; Ha, H.; Pargellis, C.; Waldmeier, F.; Swanson, S.; Murthy, P. P. N. Bioorg. Chem. 1985, 13, 246-265.
30. (b) Cane, D. E.; Yang, G.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454-3462.
31. (c) Cane, D. E.; Ha, H. J. Am. Chem. Soc. 1988, 110, 6865-6870.
32. (d) Cane, D. E.; Yang, G.; Xue, Q.; Shim, J. H. Biochemistry 1995, 34, 2471-2479.
33. Vedula, L. S.; Rynkiewicz, M. J.; Pyun, H. J.; Coates, R. M.; Cane, D. E.; Christianson, D. W. Biochemistry 2005, 44, 6153-6163.
34. Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. Biochemistry 2002, 41, 1732-1741.
35. Vedula, L. S.; Cane, D. E.; Christianson, D. W. Biochemistry 2005, 44, 12719-12727.
36. Cane, D. E.; Xue, Q.; Fitzsimons, B. C. Biochemistry 1996, 35, 12369-12376.
37. Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. Proc. Natl. Acad. Sci. USA. 2001, 98, 13543-13548.
38. (a) Xiao, X.-y.; Prestwich, G. D. J. Am. Chem. Soc. 1991, 113, 9673-9674.
39. (b) Croteau, R.; Alonso, W. R.; Koepp, A. E.; Shim, J. H.; Cane, D. E. Arch. Biochem. Biophys. 1993, 307, 397-404.
40. (c) Cane, D. E.; Bryant, C. J. Am. Chem. Soc. 1994, 116, 12063-12064.
41. (d) Poulter, C. D.; Muehlbacher, M.; Davis, D. R. J. Am. Chem. Soc. 1989, 111, 3740-3742.
42. Cane, D. E.; Bowser, T. E. Bioorg. Med. Chem. Lett. 1999, 9, 1127-1132.
43. (a) Peters, R. In Carbon-Fluorine Compounds: Chemistry, Biochemistry and Biological Activities; Associated Scientific Publishers: Amsterdam; a Ciba Foundation Symposium: London, 1972.
44. (b) Filler, R. In Biochemistry involving Carbon-Fluoride Bonds; ACS Symp., 1976, Ser. No. 28.
45. (c) Walsh, C. T. Adv. Enzymol. Relat. Areas Mol. Biol. 1983, 55, 197.
46. (d) McCarter, J. D.; Withers, S. G. J. Am. Chem. Soc. 1996, 118, 241-242.
47. (e) Vendittis, E. D.; Ursby, T.; Rullo, R.; Gogliettino, M. A.; Masullo, M.; Bocchini, V. Eur. J. Biochem. 2001, 268, 1794-1801.
48. (f) He, Z.; Stigers Lavoie, K. D.; Bartlett, P. A.; Toney, M. D. J. Am. Chem. Soc. 2004, 126, 2378-2385.
49. (g) Storici, P.; Qiu, J.; Schirmer, T.; Silverman, R. B. Biochemistry 2004, 43, 14057-14063.
50. (h) Hong, S.-B.; Mullins, L. S.; Shim, H.; Raushel, F. M. Biochemistry 1997, 36, 9022-9028.
51. (a) Street, I. P.; Poulter, C. D. Biochemistry 1990, 29, 7531-7538.
52. (b) Meulbacher, M.; Poulter, C. D. Biochemistry 1988, 27, 7315-7328.
53. (c) Wouters, J.; Oudjama, Y.; Stalon, V.; Droogmans, L.; Poulter, C. D. PROTEINS: Structure, Function, and Bioinformatics 2004, 54, 216-221.
54. Cane, D. E.; Chiu, H.-T.; Liang, P.-H.; Anderson, K. S. Biochemistry 1997, 36, 8332-8339.
55. Sharpless, K. B.; Umbreit, M. A. J. Am. Chem. Soc. 1977, 99, 5526-5528.
56. (a) Corey, E. J.; Volante, R. P. J. Am. Chem. Soc. 1976, 98, 1291-1293.
57. (b) Biller, S. A.; Forster, C.; Gordon, E. M.; Harrity, T.; Scott, W. A.; Ciosek, C. P. Jr. J. Med. Chem. 1988, 31, 1869-1871.
58. (c) Biller, S. A.; Forster, C. Tetrahedron 1990, 46, 6645-6658.
59. Valentijn, A. R. P. M.; van der Marel, G. A.; Cohn, L. H.; van Boom, J. H. Synlett 1991, 2, 155-156.
60. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; Mekenna, M.-C. Tetrahedron Lett. 1977, 2, 155.
61. Bertolino, A.; Altman, L. J.; Vasak, J.; Rilling, H. C. Biochim. Biophys. Acta. 1978, 530, 17.
62. (a) Cane, D. E. Tetrahedron 1980, 36, 1109-1159.
63. (b) Cane, D. E.; Iyengar, R.; Shiao, M.-S. J. Am. Chem. Soc. 1981, 103, 914-931.
64. (c) Poulter, C. D.; Rilling, H. C. In Biosynthesis of Isoprenoid Compounds; Porter, J. W. & Spurgen, S. L., Eds.; John Wiley: New York, 1981.
65. (a) Wheeler, C. J.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1987, 262, 8213.
66. (b) Wheeler, C. J.; Croteau, R. Arch. Biochem. Biophys. 1988, 260, 250-256.
67. Cane, D. E.; Yang, G.; Coates, R. M.; Pyun, H.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454-3462.
68. (a) McClard, R. W.; Fujita, T. S.; Stremlar, K. E.; Poulter, C. D. J. Am. Chem. Soc. 1987, 109, 5544-5545.
69. (b) Nieschalk, J.; O'Hagan, D. J. Chem. Soc. Chem. Common. 1995, 7, 719-720.
70. Cohen, L. S.; Valentijn, A. R. P. M.; Roodenburg, L.; van Leeuwen, R. E. W.; Huisman, R. H.; Lutz, R. J.; van der Marel, G. A.; van Boom, J. H. Biochem. Pharm. 1995, 49, 839-845.
71. (a) Dougherty, D. A. Science 1996, 271, 163-168.
72. (b) Biswas, K. M.; Jackson, A. H. J. Chem. Soc. Perkin. Trans. I 1989, 11, 1981-1986.
73. (c) Abdullah, M. I.; Jackson, A. H.; Lynch, P. P.; Record, K. A. Heterocycles 1990, 30, 317-320.
74. Cane, D. E.; Yang, G. J. Org. Chem. 1994, 59, 5794-5798.
75. (a) Xue, Q. In Mechanistic Studies of Trichodiene Synthase; Ph.D. Thesis 1997, Brown University, Providence.
76. (b) Weiner, S. W. In The Biosynthesis of Pentalenene and the Design of Active Site Directed Inhibitors of Pentalenene Synthase; Ph.D. Thesis 1993, Brown University, Providence.