Cyclopropyl containing fatty acids as mechanistic probes for cytochromes P450

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2455-2469

  Cryle, Max J ^a   Ortiz De Montellano, Paul R ^b   De Voss, James J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ENZYMES; HYDROXYLATION; ISOMERIZATION; ISOMERS; OXIDATION; OXYGEN; POSITIVE IONS;

ALIPHATIC HYDROXYLATION; CYTOCHROMES; MECHANISTIC PROBES; REGIOCHEMISTRY;

FATTY ACIDS;

ALCOHOL; CYCLOPROPANE DERIVATIVE; CYTOCHROME P450; FATTY ACID; OXYGEN;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; HYDROXYLATION; OXIDATION; REACTION ANALYSIS;

CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MOLECULAR PROBES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION;

EID: 17044367457     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047985d     Document Type: Article

References (49)

1. Ortiz de Montellano, P. R. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; p 245.
2. Cryle, M. J.; Stok, J. E.; De Voss, J. J. Aus. J. Chem. 2003, 56, 749-762.
3. Ortiz de Montellano, P. R.; De Voss, J. J. Nat. Prod. Rep. 2002, 19, 477-493.
4. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-20.
5. Auclair, K.; Hu, Z.; Little, D. M.; Ortiz de Montellano, P. R.; Groves, J. T. J. Am. Chem. Soc. 2002, 124, 6020-6027.
6. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-707.
7. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-98.
8. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921.
9. Newcomb, M.; Shen, R.; Choi, S.-Y.; Toy, P. H.; Hollenberg, P. F.; Vaz, A. D. N.; Coon, M. J. J. Am. Chem. Soc. 2000, 122, 2677-2686.
10. Newcomb, M.; Shen, R.; Lu, Y.; Coon, M. J.; Hollenberg, P. F.; Kopp, D. A.; Lippard, S. J. J. Am. Chem. Soc. 2002, 124, 6879-6886.
11. Toy, P. H.; Newcomb, M.; Hollenberg, P. F. J. Am. Chem. Soc. 1998, 120, 7719-7729.
12. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
13. Shaik, S.; de Visser, S. P.; Ogliaro, F.; Schwarz, H.; Schroeder, D. Curr. Opin. Chem. Biol. 2002, 6, 556-567.
14. Harris, N.; Cohen, S.; Filatov, M.; Ogliaro, F.; Shaik, S. Angew. Chem., Int. Ed. 2000, 39, 2003-2007.
15. Boddupalli, S. S.; Pramanik, B. C.; Slaughter, C. A.; Estabrook, R. W.; Peterson, J. A. Arch. Biochem. Biophys. 1992, 292, 20-28.
16. Capdevila, J. H.; Wei, S.; Helvig, C.; Falck, J. R.; Belosludtsev, Y.; Truan, G.; Graham-Lorence, S. E.; Peterson, J. A. J. Biol. Chem. 1996, 271, 22663-22671.
17. Bower, S.; Perkins, J. B.; Yocum, R. R.; Howitt, C. L.; Rahaim, P.; Pero, J. J. Bacteriol. 1996, 178, 4122-4130.
18. Cryle, M. J.; Matovic, N. J.; De Voss, J. J. Org. Lett. 2003, 5, 3341-3344.
19. Stok, J. E.; De Voss, J. J. Arch. Biochem. Biophys. 2000, 384, 351-360.
20. Cryle, M. J.; De Voss, J. J. Chem. Commun. 2004, 86-87.
21. Puchkaev, A. V.; Wakagi, T.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 2002, 124, 12682-12683.
22. Koo, L. S.; Immoos, C. E.; Cohen, M. S.; Farmer, P. J.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 2002, 124, 5684-5691.
23. McLean, M. A.; Maves, S. A.; Weiss, K. E.; Krepich, S.; Sligar, S. G. Biochem. Biophys. Res. Commun. 1998, 252, 166-172.
24. Cryle, M. J.; Stuthe, J. M. U.; Ortiz de Montellano, P. R.; De Voss, J. J. Chem. Commun. 2004, 512-513.
25. 16 fatty acids as this represents the longest carbon chain in the molecule.
26. If an acid and the corresponding methyl ester are discussed in this paper, a compound number followed by an "a" indicates the acid, and the compound number alone indicates the ester.
27. Villorbina, G.; Roura, L.; Camps, F.; Joglar, J.; Fabrias, G. J. Org. Chem, 2003, 68, 2820-2829.
28. Zhiqiang, Y.; Lorenz, J. C.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621-8624.
29. Kazuta, Y.; Abe, H.; Yamamoto, T.; Matsuda, A.; Shuto, S. J. Org. Chem. 2003, 68, 3511-3521.
30. Mino, T.; Fukui, S.; Yamashita, M. J. Org. Chem. 1997, 62, 734-735.
31. Yamashita, M.; Matsumiya, K.; Nakano, K. Bull. Chem. Soc. Jpn. 1993, 66, 1759-1763.
32. Schreiber, S. L.; Claus, R. E.; Reagan, J. Tetrahedron Lett. 1982, 23, 3867-3870.
33. Olah, G. A.; Reddy, V. P.; Prakash, G. K. S. Chem. Rev. 1992, 92, 69-95.
34. Newcomb, M.; Le Tadic, M.-H.; Putt, D. A.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 3312-3313.
35. Kawamura, K.; Gagosian, R. B. J. Chromatogr. 1988, 438, 309-317.
36. Kerwin, J. L.; Torvik, J. J. Anal. Biochem. 1996, 237, 56-64.
37. Wilson, R.; Smith, R.; Wilson, P.; Shepherd, M. J.; Riemersma, R. A. Anal. Biochem. 1997, 248, 76-85.
38. He, X.; Ortiz de Montellano, P. R. J. Biol. Chem. 2004, 279, 39479-39484.
39. Truan, G.; Komandla, M. R.; Falck, J. R.; Peterson, J. A. Arch. Biochem. Biophys. 1999, 366, 192-198.
40. de Visser, S. P.; Kumar, D.; Cohen, S.; Shacham, R.; Shaik, S. J. Am. Chem. Soc. 2004, 126, 8362-8363.
41. Korzekwa, K. R.; Jones, J. P.; Gillette, J. R. J. Am. Chem. Soc. 1990, 112, 7042-7046.
42. White, R. E.; McCarthy, M. B.; Egeberg, K. D.; Sligar, S. G. Arch. Biochem. Biophys. 1984, 228, 493-502.
43. Frommer, U.; Ullrich, V.; Staudinger, H. Hoppe-Seyler's Z. Physiol. Chem. 1970, 351, 903-912.
44. Murataliev, M. B.; Trinh, L. N.; Moser, L. V.; Bates, R. B.; Feyereisen, R.; Walker, F. A. Biochemistry 2004, 43, 1771-1780.
45. Coupling is the ratio of product formation to NAD(P)H consumption.
46. Puchkaev, A. V.; Ortiz de Montellano, P. R. Arch. Biochem. Biophys. 2005, 434, 169-177.
47. Koo, L. S.; Tschirret-Guth, R. A.; Straub, W. E.; Moenne-Loccoz, P.; Loehr, T. M.; Ortiz de Montellano, P. R. J. Biol. Chem. 2000, 275, 14112-14123.
48. Hakogi, T.; Shigenari, T.; Katsumura, S.; Sano, T.; Kohno, T.; Igarashi, Y. Bioorg. Med. Chem. Lett. 2003, 13, 661-664.
49. Sharma, A.; Chattopadhyay, S. J. Org. Chem. 1998, 63, 6128-6131.