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Metabolism of all-trans, 9-cis, and 13-cis isomers of retinal by purified isozymes of microsomal cytochrome P450 and mechanism-based inhibition of retinoid oxidation by citral.
Evidence was obtained that citral is an effective mechanism-based inactivator of isozyme 2B4, with a KI of 44 microM as determined by the oxidation of 1-phenylethanol to acetophenone, and by isozyme 1A2 in the oxidation and 4-hydroxylation of all-trans-retinol and retinoic acid.
Spectroscopic investigations of intermediates in the reaction of cytochrome P450(BM3)-F87G with surrogate oxygen atom donors.
Characterization of the cytochrome P450 CYP2J4: expression in rat small intestine and role in retinoic acid biotransformation from retinal.
- Q. Y. Zhang, G. Raner, X. Ding, D. Dunbar, M. J. Coon, L. Kaminsky
- Biology, MedicineArchives of biochemistry and biophysics
- 15 May 1998
It is determined that purified, heterologously expressed CYP2J4 is active toward all-trans- and 9-cis-retinal in reconstituted systems, producing the corresponding retinoic acids as the major products.
Effects of herbal products and their constituents on human cytochrome P450(2E1) activity.
Peroxo-iron and oxenoid-iron species as alternative oxygenating agents in cytochrome P450-catalyzed reactions: switching by threonine-302 to alanine mutagenesis of cytochrome P450 2B4.
- A. Vaz, S. J. Pernecky, G. Raner, M. J. Coon
- Chemistry, BiologyProceedings of the National Academy of Sciences…
- 14 May 1996
It is concluded that the iron-peroxy species is the direct oxygen donor in P450-catalyzed oxygenation reactions and which of the many other oxidative reactions involving P450 utilize this species and the extent to which peroxo-iron and oxenoid-iron function as alternative oxygenating agents with the numerous isoforms of this versatile catalyst.
C. fumago chloroperoxidase is also a dehaloperoxidase: oxidative dehalogenation of halophenols.
- Robert L. Osborne, G. Raner, L. Hager, J. Dawson
- Chemistry, BiologyJournal of the American Chemical Society
- 4 January 2006
The relative catalytic efficiency of CCPO reported herein is comparable to that of horseradish peroxidase and an electron-transfer mechanism is proposed that accounts for the products formed from both the 2,4,6-trihalo- and p-halophenols.
Mechanism-based inactivation of cytochrome P450 2B4 by aldehydes: relationship to aldehyde deformylation via a peroxyhemiacetal intermediate.
It is concluded that inactivation of P450 by aldehydes occurs via homolytic cleavage of a peroxyhemiacetal intermediate to give an alkyl radical that reacts with the heme.
Oxidative cleavage of esters and amides to carbonyl products by cytochrome P450.
- H. M. Peng, G. Raner, A. Vaz, M. J. Coon
- Chemistry, BiologyArchives of biochemistry and biophysics
- 20 April 1995
It is established that oxidative cleavage is a widespread reaction among P450 cytochromes and commonly used esters and amides and also rule out the possibility of transient ester hydrolysis with subsequent oxidation of the alcohol formed.
The mechanism of oxidative halophenol dehalogenation by Amphitrite ornata dehaloperoxidase is initiated by H2O2 binding and involves two consecutive one-electron steps: role of ferryl intermediates.
- Robert L. Osborne, M. Coggins, G. Raner, M. Walla, J. Dawson
- Chemistry, BiologyBiochemistry
- 29 April 2009
It is shown in single-turnover experiments that the DHP Fe(IV)O intermediate is an active oxidant in halophenol oxidative dehalogenation and reaction of DHP with 4-chlorophenol leads to a dimeric product.
Membrane topology of cytochrome P450 2B4 in Langmuir-Blodgett monolayers.
- M. Shank-Retzlaff, G. Raner, M. J. Coon, S. Sligar
- Biology, ChemistryArchives of biochemistry and biophysics
- 1 November 1998
The membrane topology of P450 2B4 was characterized and its insertion area in DPPE monolayers was measured and analyzed with use of the Gibbs equation for adsorption at an interface to suggest that this cytochrome is not deeply embedded but that other regions, in addition to the amino-terminal 26 residues, may be involved in the interaction of cy tochrome P450 with the membrane.