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Hypersensitive Radical Probes and the Mechanisms of Cytochrome P450-Catalyzed Hydroxylation Reactions
Abstract
The title probes are precursors to kinetically calibrated, aryl-substituted cyclopropylcarbinyl radicals that rearrange with picosecond lifetimes. Applications in studies of cytochrome P450-catalyzed hydroxylation reactions are reviewed. Initially confusing results regarding lifetimes of radicals in the hydroxylation reactions were resolved when second-generation probes that distinguish between radicals and cations were employed. The results indicate that two electrophilic oxidizing species are involved in P450-catalyzed hydroxylations, an iron-oxo species that inserts oxygen and a hydroperoxo-iron species that inserts OH(+). The cationic rearrangement products are ascribed to reactions of the protonated alcohol products formed from the latter.
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Citations
Cited by
Heme 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
Merkx, M., Kopp, D. A., Sazinsky, M. H., Blazyk, J. L., Müller, J., & Lippard, S. J. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20010803)40:15<2782::aid-anie2782>3.3.co;2-g · Cited by 659
O–H hydrogen bonding promotes H-atom transfer from α C–H bonds for C-alkylation of alcohols
Jeffrey, J. L., Terrett, J. A., & MacMillan, D. W. C. (2015) · Science · doi:10.1126/science.aac8555 · Cited by 594
Reactivity of High-Valent Iron–Oxo Species in Enzymes and Synthetic Reagents: A Tale of Many States
Shaik, S., Hirao, H., & Kumar, D. (2007) · Accounts of Chemical Research · doi:10.1021/ar600042c · Cited by 555
Metadata
- Authors
- Newcomb, M., & Toy, P. H.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-04-26
- Volume
- 33
- Issue
- 7
- Pages
- 449-455
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- OpenAlex
- W2059426878
- Cited by
- 274
- References
- 0
- FWCI
- 17.17
- Type
- journal article
- Language
- en
- Open access
- closed
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