Hypersensitive radical probe studies of chloroperoxidase-catalyzed hydroxylation reactions

Chemical Research in Toxicology

Volumn 11, Issue 7, 1998, Pages 816-823

  Toy, Patrick H ^a   Newcomb, Martin ^a   Hager, Lowell P ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE PEROXIDASE;

ARTICLE; ENZYME ACTIVE SITE; ENZYME ACTIVITY; HYDROXYLATION; OXIDATION; STRUCTURE ACTIVITY RELATION;

CATALYSIS; CHLORIDE PEROXIDASE; CYCLOPROPANES; FREE RADICALS; HYDROXYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MITOSPORIC FUNGI; OXIDATION-REDUCTION;

EID: 0031823396     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9800295     Document Type: Article

References (33)

1. Sundaramoorthy, M., Terner, J., and Poulos, T. L. (1995) The crystal structure of chloroperoxidase: a heme peroxidase-cytochrome P450 functional hybrid. Structure 3, 1367-77.
2. Franssen, M. C. R., and van der Plas, H. C. (1992) Haloperoxidases: Their properties and their use in organic synthesis. Adv. Appl. Microbiol. 37, 41-99.
3. Groves, J. T., and Han, Y.-Z. (1995) Models and Mechanisms of Cytochrome P450 Action. In Cytochrome P450 Structure, Mechanism and Biochemistry, 2nd ed. (Ortiz de Montellano, P. R., Ed.) pp 3-48, Plenum, New York.
4. Guengerich, F. P., and Macdonald, T. L. (1990) Mechanisms of cytochrome P-450 catalysis. FASEB J. 4, 2453-2459.
5. Woggon, W. D., and Fretz, H. (1992) Mechanisms of cytochrome P-450 catalyzed oxidations. In Advances in Detailed Reaction Mechanisms (Coxon, J. M., Ed.) Vol. 2, pp 111-147, JAI Press, Greenwich, CT.
6. Newcomb, M., Le Tadic, M. H., Putt, D. A., and Hollenberg, P. F. (1995) An incredibly fast apparent oxygen rebound rate constant for hydrocarbon hydroxylation by cytochrome P-450 enzymes. J. Am. Chem. Soc. 117, 3312-3313.
7. Newcomb, M., Le Tadic-Biadatti, M. H., Chestney, D. L., Roberts, E. S., and Hollenberg, P. F. (1995) A nonsynchronous concerted mechanism for cytochrome P-450 catalyzed hydroxylation. J. Am. Chem. Soc. 117, 12085-12091
8. Toy, P. H., Dhanabalasingam, B., Newcomb, M., Hanna, I. M., and Hollenberg, P. F. (1997) A substituted hypersensitive radical probe for enzyme-catalyzed hydroxylations: Synthesis of racemic and enantiomerically enriched forms and application in a cytochrome P450-catalyzed oxidation. J. Org. Chem. 62, 9114-9122.
9. Newcomb, M., and Le Tadic-Biadatti, M.-H. (1997) Hypersenstive probing for radicals in cytochrome P450 hydroxylations. In Free Radicals in Biology and the Environment (Minisci, F., Ed.) pp 91-108, Kluwer Academic Publishers, Dordrecht, The Netherlands.
10. McCarthy, M.-B., and White, R. E. (1983) Functional differences between peroxidase compound I and the cytochrome P-450 reactive oxygen intermediate. J. Biol. Chem. 258, 9153-9158.
11. Zaks, A., and Dodds, D. R. (1995) Chloroperoxidase-catalyzed asymmetric oxidations: Substrate specificity and mechanistic study. J. Am. Chem. Soc. 117, 10419-10424.
12. Miller, V. P., Tschirretguth, R. A., and Ortiz de Montellano, P. R. (1995) Chloroperoxidase-catalyzed benzylic hydroxylation. Arch. Biochem. Biophys. 319, 333-340.
13. Newcomb, M., Johnson, C. C., Manek, M. B., and Varick, T. R. (1992) Picosecond radical kinetics Ring openings of phenyl substituted cyclopropylcarbinyl radicals. J. Am. Chem. Soc. 114, 10915-10921.
14. Atkinson, J. K., and Ingold, K. U. (1993) Cytochrome P450 hydroxylation of hydrocarbons: variation in the rate of oxygen rebound using cyclopropyl radical clocks including two new ultrafast probes. Biochemistry 32, 9209-9214.
15. Atkinson, J. K., Hollenberg, P. F., Ingold, K. U., Johnson, C. C., Le Tadic, M.-H., Newcomb, M., and Putt, D. A. (1994) Cytochrome P450-catalyzed hydroxylation of hydrocarbons: kinetic deuterium isotope effects for the hydroxylation of an ultrafast radical clock. Biochemistry 33, 10630-10637.
16. Liu, K. E., Johnson, C. C., Newcomb, M., and Lippard, S. J. (1993) Radical clock substrate probes and kinetic isotope effect studies of the hydroxylation of hydrocarbons by methane monooxygenase. J. Am. Chem. Soc. 115, 939-947.
17. Newcomb, M., Simakov, P. A., and Park, S.-U. (1996) Hypersensitive radical probe studies of Gif oxidations. Tetrahedron Lett. 37, 819-822.
18. Allain, E. J., Hager, L. P., Deng, L., and Jacobsen, E. N. (1993) Highly enantioselective epoxidation of disubstituted alkenes with hydrogen peroxide catalyzed by chloroperoxidase. J. Am. Chem. Soc. 115, 4415-4416.
19. Vogel, A. (1989) Vogel's Textbook of Practical Organic Chemistry, 5th ed., p 432, Longman Scientific and Technical, Essex, England.
20. Rodriques, K. E. (1991) A novel route to cyclopropyl ketones. aldehydes, and carboxylic acids. Tetrahedron Lett. 32, 1275-1278.
21. Harada, T., Katsuhira, T., Hattori, K., and Oku, A. (1993) Stereoselective carbon-carbon bond forming reaction of 1,1-dibromocyclopropanes via 1-halocyclopropylzincates. J. Org. Chem. 58, 2958-2965.
22. + with alkenes and alkynes. Observation of efficient benzylidene-transfer reactions. J. Am. Chem. Soc. 102, 7802-7803.
23. Perkins, M. J., Peynircioglu, N. B., and Smith, B. V. (1978) The preparation and rates of deprotonation of some cyclopropylcarbinyl ketones. J. Chem. Soc., Perkin Trans. 2 1025-1033.
24. Yamaguchi, M., and Hirao, I. (1984) An intramolecular nucleophilic substitution of oxetanes. Tetrahedron Lett. 25, 4549-4552.
25. DePuy, C. H., Dappen, G. M., Eilers, K. L., and Klein, R. A. (1964) The chemistry of cyclopropanols. II. Synthetic methods. J. Org. Chem. 29, 2813-2815.
26. 2 in the presence of an ether. J. Am. Chem. Soc. 118, 4539-4549.
27. Iqbal, J., and Joseph, S. P. (1989) Cobalt mediated regioreversed addition of but-2-eneyltributylstannane to aldehydes. Tetrahedron Lett. 30, 2421-2422.
28. Mathias, R., and Weyerstahl, P. (1979) Darstellung und eigenschaften von 1,1-diiod- und 1-iod-1-x-cyclopropanen. Chem. Ber. 112, 3041-3053.
29. Padwa, A., Rodriguea, R., Tohidi, M., and Fukunaga, T. (1983) Intramolecular cycloaddition reactions of diazoalkenes. A theoretical prognosis of nitrene type behavior. J. Am. Chem. Soc. 105, 933-943.
30. Vaz, A. D. N., McGinnity, D. F., and Coon, M. J. (1998) Epoxidation of olefins by cytochrome P450: Evidence from site-specific mutagenesis for hydroperoxo-iron as an electrophilic oxidant. Proc. Natl Acad. Sci. U.S.A. 95, 3555-3560.
31. Dexter, A, F., and Hager, L. P. (1995) Transient heme N-alkylation of chloroperoxidase by terminal alkenes and alkynes. J. Am. Chem. Soc. 117, 817-818.
32. Priestley, N. D., Floss, H. G. Froland, W. A., Lipscomb, J. D., Williams, P. G., and Morimoto, H. (1992) Cryptic stereospecificity of methane monooxygenase. J. Am. Chem. Soc. 114, 7561-7562.
33. Valentine, A. M., Wilkinson, B., Liu, K. E., Komar-Panicucci, S., Priestley, N. D., Williams, P. G., Morimoto, H., Floss, H. G., and Lippard, S. J. (1997) Tritiated chiral alkanes as substrates for soluble methane monooxygenase from Methylococcus capsulatus (Bath): probes for the mechanism of hydroxylation. J. Am. Chem. Soc. 119, 1818-1827.