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Kinetic Characterization of Compound I Formation in the Thermostable Cytochrome P450 CYP119
Open accessAbstract
The kinetics of formation and breakdown of the putative active oxygenating intermediate in cytochrome P450, a ferryl-oxo-(pi) porphyrin cation radical (Compound I), have been analyzed in the reaction of a thermostable P450, CYP119, with meta-chloroperoxybenzoic acid (m-CPBA). Upon rapid mixing of m-CPBA with the ferric form of CYP119, an intermediate with spectral features characteristic of a ferryl-oxo-(pi) porphyrin cation radical was clearly observed and identified by the absorption maxima at 370, 610, and 690 nm. The rate constant for the formation of Compound I was 3.20 (+/-0.3) x 10(5) m(-1) s(-1) at pH 7.0, 4 degrees C, and this rate decreased with increasing pH. Compound I of CYP119 decomposed back to the ferric form with a first order rate constant of 29.4 +/- 3.4 s(-1), which increased with increasing pH. These findings form the first kinetic analysis of Compound I formation and decay in the reaction of m-CPBA with ferric P450.
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Cited by
Structure and chemistry of cytochrome p450
Denisov, I. G., Makris, T. M., Sligar, S. G., & Schlichting, I. (2005) · Chemical Reviews · doi:10.1021/cr0307143 · Cited by 2,106
Self-citationHeme Enzyme Structure and Function
Poulos, T. L. (2014) · Chemical Reviews · doi:10.1021/cr400415k · Cited by 1,443
P450 Enzymes: Their Structure, Reactivity, and Selectivity—Modeled by QM/MM Calculations
Shaik, S., Cohen, S., Wang, Y., Chen, H., Kumar, D., & Thiel, W. (2010) · Chemical Reviews · doi:10.1021/cr900121s · Cited by 1,083
Schöneboom, J. C., Lin, H., Reuter, N., Thiel, W., Cohen, S., Ogliaro, F., & Shaik, S. (2002) · Journal of the American Chemical Society · doi:10.1021/ja026279w · Cited by 309
Davydov, R., Gilep, A. A., Strushkevich, N. V., Usanov, S. A., & Hoffman, B. M. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3067226 · Cited by 49
Metadata
- Authors
- Kellner, D. G., Hung, S.-C., Weiss, K. E., & Sligar, S. G.
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2002-03
- Volume
- 277
- Issue
- 12
- Pages
- 9641-9644
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W2072975767
- Cited by
- 222
- References
- 0
- FWCI
- 13.53
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Kellner, D. G., Hung, S.-C., Weiss, K. E., & Sligar, S. G. (2002). Kinetic Characterization of Compound I Formation in the Thermostable Cytochrome P450 CYP119. Journal of Biological Chemistry. https://doi.org/10.1074/jbc.c100745200
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