Vanadium haloperoxidase-catalyzed bromination and cyclization of terpenes

Journal of the American Chemical Society

Volumn 125, Issue 13, 2003, Pages 3688-3689

  Carter Franklin, Jayme N ^a   Parrish, Jon D ^a   Tschirret Guth, Richard A ^a   Little, R Daniel ^a   Butler, Alison ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA SNYDEROL; BETA SNYDEROL; LAURENCIN; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM; VANADIUM HALOPEROXIDASE;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ENZYME ACTIVE SITE; ENZYME ANALYSIS; RED ALGA;

ALGAE, RED; CATALYSIS; CYCLIZATION; HYDROCARBONS, BROMINATED; PEROXIDASES; TERPENES;

EID: 0037414322     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029271v     Document Type: Article

References (26)

1. Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48 and references therein.
2. Fenical, W. J. Phycol. 1975, 11, 245-259.
3. Fusetani, N. Drugs from the Sea; Karger Press: Basel, Switzerland, 2000.
4. Wolinsky, L. E.; Faulkner, D. J. J. Org. Chem. 1976, 41, 597-600.
5. Howard, B. M.; Fenical, W. Tetrahedron. Lett. 1976, 29, 2519-2520.
6. Kato, T.; Ichinose, I.; Kamoshida, A.; Kitahara, Y. J. Chem. Soc., Chem. Commun. 1976, 518-519. Kato. T.; Ishii, K.; Ichinose, I.; Nakai, Y.; Kumagai, T. J. Chem. Soc., Chem. Commun. 1980, 1106-1108.
7. Kato, T.; Ichinose, I.; Kamoshida, A.; Kitahara, Y. J. Chem. Soc., Chem. Commun. 1976, 518-519. Kato. T.; Ishii, K.; Ichinose, I.; Nakai, Y.; Kumagai, T. J. Chem. Soc., Chem. Commun. 1980, 1106-1108.
8. Gonzalez, A. G.; Martin, J. D.; Perez, C.; Ramirez, M. A. Tetrahedron Lett. 1976, 2, 137-138.
9. van Tamelen, E.; Hessler, E. J. J. Chem. Soc., Chem. Commun. 1966, 411-413. van Tamelen, E. Acc. Chem. Res. 1968, 1, 111-120.
10. van Tamelen, E.; Hessler, E. J. J. Chem. Soc., Chem. Commun. 1966, 411-413. van Tamelen, E. Acc. Chem. Res. 1968, 1, 111-120.
11. Manthey, J. A.; Hager, L. P. J. Biol. Chem. 1985, 260, 9654-9659.
12. Vilter, H. Phytochemistry 1984, 23, 1387-1390.
13. Martinez, J. S.; Carroll, G. L.; Tschirret-Guth, R. A.; Altenhoff, G.; Little, R. D.; Butler, A. J. Am. Chem. Soc. 2001, 123, 3289-3294.
14. Butler, A.; Carter, J. N.; Simpson, M. T. In Handbook on Metalloproteins; Bertini, I., Sigel, A., Sigel, H., Eds.: M. Dekker: New York, 2001; pp 153-179.
15. Hemrika, W.; Renirie, R.; Dekker: H.; Wever, R. ACS Symp. Ser. 1998, 711, 216-227.
16. Isupov, M. N.; Dalby, A. R.; Brindley, A. A.; Izumi, Y.; Tanabe, T.; Murshudov, G. N.; Littlechild, J. A. J. Mol. Biol. 2000, 299, 1035-1049.
17. Weyand, M.; Hecht, H.; Kiesz, M.; Liaud, M. F.; Vitler, H.; Schomburg, D. J. Mol. Biol. 1999, 293, 595-611.
18. Irie, T.; Susuki, M.; Masumune, T. Tetrahedron Lett, 1965, 16, 1091-1099.
19. Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron 1968, 24, 4193-4205.
20. 2 (added over 4 h by syringe pump), in 0.15 M phosphate buffer, pH 5.7 containing 30% v/v ethanol, 40 mM KBr, and 25 nM V-BrPO (C. officinalis). The reactions were allowed to proceed until all of the substrate had been consumed as judged by GC-MS. Bromination and cyclization of substrates does not occur in the absence of V-BrPO.
21. Faulkner, D. J. Phytochemistry 1976, 15, 1993-1994.
22. 2 and V-BrPO in 0.15 M phosphate buffer, pH 5.7 containing 30% v/v ethanol, 40 mM KBr at room temperature.
23. Gonzalez, I. C.; Forsyth, C. J. J. Am. Chem. Soc. 2000, 122, 9099-9108.
24. Ishihara, J.; Kanoh, N.; Murai, A. Tetrahedron Lett. 1995, 36, 737-740.
25. The NMR spectra of 7, 8, and 10 are identical to that previously reported in ref 4.
26. Hoye, T. R.; Caruso, A. J.; Kurth, M. J. J. Org. Chem. 1981, 46, 3550-3552.