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Article: Hypersensitive radical and the mechanisms of cytochrome P450-catalyzed hydroxylation reactions

TitleHypersensitive radical and the mechanisms of cytochrome P450-catalyzed hydroxylation reactions
Authors
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/achre4/about.html
Citation
Accounts Of Chemical Research, 2000, v. 33 n. 7, p. 449-455 How to Cite?
AbstractThe 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.
Persistent Identifierhttp://hdl.handle.net/10722/167634
ISSN
2015 Impact Factor: 22.003
2015 SCImago Journal Rankings: 11.465
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorNewcomb, Men_US
dc.contributor.authorToy, PHen_US
dc.date.accessioned2012-10-08T03:09:18Z-
dc.date.available2012-10-08T03:09:18Z-
dc.date.issued2000en_US
dc.identifier.citationAccounts Of Chemical Research, 2000, v. 33 n. 7, p. 449-455en_US
dc.identifier.issn0001-4842en_US
dc.identifier.urihttp://hdl.handle.net/10722/167634-
dc.description.abstractThe 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.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/achre4/about.htmlen_US
dc.relation.ispartofAccounts of Chemical Researchen_US
dc.titleHypersensitive radical and the mechanisms of cytochrome P450-catalyzed hydroxylation reactionsen_US
dc.typeArticleen_US
dc.identifier.emailToy, PH:phtoy@hkucc.hku.hken_US
dc.identifier.authorityToy, PH=rp00791en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ar960058ben_US
dc.identifier.pmid10913233-
dc.identifier.scopuseid_2-s2.0-0033623690en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0033623690&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume33en_US
dc.identifier.issue7en_US
dc.identifier.spage449en_US
dc.identifier.epage455en_US
dc.identifier.isiWOS:000088521700002-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridNewcomb, M=7101865783en_US
dc.identifier.scopusauthoridToy, PH=7006579247en_US
dc.identifier.citeulike5828832-

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