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Kinetic Isotope Effects Implicate Two Electrophilic Oxidants in Cytochrome P450-Catalyzed
Hydroxylations.
Newcomb, Martin; Aebisher, David; Shen, Runnan; Chandrasena, R. Esala P.; Hollenberg,
Paul F.; Coon, Minor J. Department of Chemistry, University of Illinois, Chicago, IL, USA. Journal of the
American Chemical Society (2003), 125(20), 6064-6065. Publisher: American Chemical Society, CODEN:
JACSAT ISSN: 0002-7863. Journal written in English. CAN 139:49057 AN 2003:320273 CAPLUS
Abstract
Intramol. kinetic isotope effects (KIEs) were detd. for cytochrome P 450-catalyzed hydroxylation reactions of
methyl-dideuterated trans-2-phenylcyclopropylmethane-d2 (1-d2), which gives two products from oxidn. of the
Me group, trans-2-phenylcyclopropylmethanol (2) and 1-phenyl-3-buten-1ol (3). In oxidns. of each enantiomer
of 1-d2 with three P 450 enzymes (CYP2B1, CYP2E1, and CYP2E1 T303A), the apparent intramol. KIEs
were different for products 2 and 3 in all cases and different for each enzyme-substrate combination. In oxidns.
of each enantiomer of undeuterated 1-d0 and trideuteriomethyl 1-d3 by CYP2B1 and CYP2E1, the ratio of
products 2/3 decreased for 1-d3 in comparison to 1-d0 in all cases. The results require multiple pathways for P
450-catalyzed hydroxylation and are consistent with the "two-oxidants" model, where hydroxylation is effected
by both the hydroperoxy-iron species and the iron-oxo species. The results are not consistent with predictions
of the "two-states" model for P 450-catalyzed hydroxylations, where oxidns. occur from a low-spin state and a
high-spin state of iron-oxo.
Indexing -- Section 7-4 (Enzymes)
Isotope effect
(deuterium; kinetic isotope effect parameters of cytochrome 450-catalyzed hydroxylations)
Hydroxylation
Oxidation
(enzymic; kinetic isotope effects implicate two electrophilic oxidants in cytochrome P 450-catalyzed
hydroxylations)
Methyl group
(kinetic isotope effects implicate two electrophilic oxidants in cytochrome P 450-catalyzed hydroxylations)
936-58-3
3170-83-0, Hydroperoxy
7439-89-6 , Iron, biological studies
7722-84-1, Hydrogen peroxide, biological studies
10488-06-9
14875-96-8, Heme
53403-04-6
61826-40-2
330196-93-5, Cytochrome P 450 2E1
330196-93-5D, Cytochrome P 450 2E1, Thr303Ala mutant
330207-10-8, Cytochrome CYP2B1
Role: BSU (Biological study, unclassified); BIOL (Biological study)
(kinetic isotope effects implicate two electrophilic oxidants in cytochrome P 450-catalyzed hydroxylations)
Supplementary Terms
kinetics isotope effect cytochrome P450 hydroxylation oxidn CYP2B1 iron
Citations
1) de Montellano, O; Cytochrome P450 Structure, Mechanism, and Biochemistry, 2nd ed 1995
[Citations 2-13 have been deleted to save space]
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Hydroxylation
=> An Index Term.
Isotope effect
.
(deuterium; kinetic isotope effect parameters of cytochrome 450-catalyzed hydroxylations)
=> The Index Term “Isotope effect” has three modifiers:
deuterium
kinetic isotope effect parameters
cytochrome 450-catalyzed hydroxylations
936-58-3
=> CAS Registry Numbers should be thought of as Index Terms.
3170-83-0, Hydroperoxy => Text next to a CAS Registry Number is either a synonym for the substance or a
modifier of the substance.
Role: BSU (Biological study, unclassified); BIOL (Biological study)
(kinetic isotope effects implicate two electrophilic oxidants in cytochrome P 450-catalyzed hydroxylations)
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Supplementary Terms
kinetics isotope effect cytochrome P450 hydroxylation oxidn CYP2B1 iron
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