Enzyme-substrate complementarity governs access to a cationic reaction manifold in the P450BM3-catalysed oxidation of cyclopropyl fatty acids

Chemistry - A European Journal

Volumn 18, Issue 50, 2012, Pages 15994-15999

  Cryle, Max J ^a,b   Hayes, Patricia Y ^a   De Voss, James J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

Author keywords

carbocation; CYP102A1; cytochromes; enzyme catalysis; oxidation

Indexed keywords

CARBOCATIONS; CATALYSED OXIDATION; CATIONIC INTERMEDIATES; CYCLOPROPYL; CYP102A1; CYTOCHROME P450; CYTOCHROME P450 BM3; DODECANOIC ACID; ENZYME CATALYSIS;

CATALYSIS; FATTY ACIDS; OXIDATION; PROBES; PROTEINS; SUBSTRATES;

ENZYMES;

CATION; CYTOCHROME P450; FATTY ACID; LAURIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; HYDROXYLATION; KINETICS; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION;

CATALYSIS; CATIONS; CYTOCHROME P-450 ENZYME SYSTEM; FATTY ACIDS; HYDROXYLATION; KINETICS; LAURIC ACIDS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION;

EID: 84870576319     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203035     Document Type: Article

References (32)

1. F. P. Guengerich, Curr. Drug Metab. 2001, 2, 93
2. M. J. Cryle, J. E. Stok, J. J. De Voss, Austr. J. Chem. 2003, 56, 749.
3. P. R. Ortiz de Montellano, Chem. Rev. 2010, 110, 932
4. P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477
5. S. Shaik, S. Cohen, Y. Wang, H. Chen, D. Kumar, W. Thiel, Chem. Rev. 2010, 110, 949.
6. J. Rittle, M. T. Green, Science 2010, 330, 933.
7. C. A. Reilly, G. S. Yost, Drug Metab. Dispos. 2005, 33, 530
8. H. Sun, W. J. Ehlhardt, P. Kulanthaivel, D. L. Lanza, C. A. Reilly, G. S. Yost, J. Pharmacol. Exp. Ther. 2007, 322, 843
9. C. J. C. Whitehouse, S. G. Bell, L.-L. Wong, Chem. Eur. J. 2008, 14, 10905.
10. P. R. Ortiz de Montellano, R. A. Stearns, J. Am. Chem. Soc. 1987, 109, 3415
11. P. R. Ortiz de Montellano, S. D. Nelson, Arch. Biochem. Biophys. 2011, 507, 95.
12. M. J. Cryle, P. R. Ortiz de Montellano, J. J. De Voss, J. Org. Chem. 2005, 70, 2455.
13. M. J. Cryle, J. M. U. Stuthe, P. R. Ortiz de Montellano, J. J. De Voss, Chem. Commun. 2004, 512.
14. M. Newcomb, R. Shen, S.-Y. Choi, P. H. Toy, P. F. Hollenberg, A. D. N. Vaz, M. J. Coon, J. Am. Chem. Soc. 2000, 122, 2677
15. M. Newcomb, R. Shen, Y. Lu, M. J. Coon, P. F. Hollenberg, D. A. Kopp, S. J. Lippard, J. Am. Chem. Soc. 2002, 124, 6879
16. P. H. Toy, M. Newcomb, P. F. Hollenberg, J. Am. Chem. Soc. 1998, 120, 7719.
17. L. A. Moe, Z. Hu, D. Deng, R. N. Austin, J. T. Groves, B. G. Fox, Biochemistry 2004, 43, 15688.
18. S. S. Boddupalli, B. C. Pramanik, C. A. Slaughter, R. W. Estabrook, J. A. Peterson, Arch. Biochem. Biophys. 1992, 292, 20.
19. D. C. Haines, D. R. Tomchick, M. Machius, J. A. Peterson, Biochemistry 2001, 40, 13456
20. H. Li, T. L. Poulos, Nat. Struct. Biol. 1997, 4, 140.
21. S. S. Boddupalli, R. W. Estabrook, J. A. Peterson, J. Biol. Chem. 1990, 265, 4233
22. L. O. Narhi, A. J. Fulco, J. Biol. Chem. 1986, 261, 7160
23. C. J. C. Whitehouse, S. G. Bell, L.-L. Wong, Chem. Soc. Rev. 2012, 41, 1218.
24. H. M. Girvan, K. R. Marshall, R. J. Lawson, D. Leys, M. G. Joyce, J. Clarkson, W. E. Smith, M. R. Cheesman, A. W. Munro, J. Biol. Chem. 2004, 279, 23274.
25. D. H. R. Barton, D. Crich, W. B. Motherwell, Tetrahedron 1985, 41, 3901.
26. J. A. Franz, B. A. Bushaw, M. S. Alnajjar, J. Am. Chem. Soc. 1989, 111, 268.
27. V. W. Bowry, J. Lusztyk, K. U. Ingold, J. Am. Chem. Soc. 1991, 113, 5687.
28. M. J. Cryle, N. J. Matovic, J. J. De Voss, Org. Lett. 2003, 5, 3341
29. M. J. Cryle, J. J. De Voss, Chem. Commun. 2004, 86.
30. J. E. Stok, J. J. De Voss, Arch. Biochem. Biophys. 2000, 384, 351
31. M. J. Cryle, I. Schlichting, Proc. Natl. Acad. Sci. USA 2008, 105, 15696.
32. Z. Su, X. Chen, J. H. Horner, M. Newcomb, Chem. Eur. J. 2012, 18, 2472.