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Oxoiron(IV) in Chloroperoxidase Compound II Is Basic: Implications for P450 Chemistry
Abstract
With the use of x-ray absorption spectroscopy, we have found that the Fe-O bond in chloroperoxidase compound II (CPO-II) is much longer than expected for an oxoiron(IV) (ferryl) unit; notably, the experimentally determined bond length of 1.82(1) Å accords closely with density functional calculations on a protonated ferryl (Fe IV -OH, 1.81 Å). The basicity of the CPO-II ferryl [p K a > 8.2 (where K a is the acid dissociation constant)] is attributable to strong electron donation by the axial thiolate. We suggest that the CPO-II protonated ferryl is a good model for the rebound intermediate in the P450 oxygenation cycle;with elevated p K a values after one-electron reduction, thiolate-ligated ferryl radicals are competent to oxygenate saturated hydrocarbons at potentials that can be tolerated by folded polypeptide hosts.
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Huang, P. L., Huang, Z., Mashimo, H., Bloch, K. D., Moskowitz, M. A., Bevan, J. A., & Fishman, M. C. (1995) · Nature · doi:10.1038/377239a0 · Cited by 2,070
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Poulos, T. L. (2014) · Chemical Reviews · doi:10.1021/cr400415k · Cited by 1,443
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Shaik, S., Cohen, S., Wang, Y., Chen, H., Kumar, D., & Thiel, W. (2010) · Chemical Reviews · doi:10.1021/cr900121s · Cited by 1,083
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Gentry, E. C., & Knowles, R. R. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00272 · Cited by 773
Schöneboom, J. C., Neese, F., & Thiel, W. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0424732 · Cited by 260
Metadata
- Authors
- Green, M. T., Dawson, J. H., & Gray, H. B.
- Venue
- Science
- Published
- 2004-06-11
- Volume
- 304
- Issue
- 5677
- Pages
- 1653-1656
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2093377100
- Cited by
- 504
- References
- 1
- FWCI
- 21.87
- Type
- journal article
- Language
- en
- Open access
- closed
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- Green, M. T., Dawson, J. H., & Gray, H. B. (2004). Oxoiron(IV) in Chloroperoxidase Compound II Is Basic: Implications for P450 Chemistry. Science. https://doi.org/10.1126/science.1096897
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