-
Radical rebound mechanism in cytochrome P-450-catalyzed hydroxylation of the multifaceted radical clocks alpha- and beta-thujone.
J Biol Chem. 2004 Sep 17;279(38):39479-84
PMID: 15258138
-
Pyrazoles as effectors of ethanol oxidizing enzymes and inducers of cytochrome P450.
Alcohol Alcohol Suppl. 1987;1:251-5
PMID: 3426688
-
Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes.
Biochemistry. 2006 Jan 17;45(2):533-42
PMID: 16401082
-
Kinetic characterization of compound I formation in the thermostable cytochrome P450 CYP119.
J Biol Chem. 2002 Mar 22;277(12):9641-4
PMID: 11799104
-
Identification of critical residues in novel drug metabolizing mutants of cytochrome P450 BM3 using random mutagenesis.
J Med Chem. 2007 Feb 8;50(3):455-61
PMID: 17266197
-
Pseudomonas putida cytochrome P-450: characterization of an oxygenated form of the hemoprotein.
Arch Biochem Biophys. 1972 Mar;149(1):197-208
PMID: 4335959
-
Sodium periodate, sodium chlorite, and organic hydroperoxides as hydroxylating agents in steroid hydroxylation reactions catalyzed by adrenocortical microsomal and mitochondrial cytochrome P450.
Arch Biochem Biophys. 1976 Jun;174(2):440-53
PMID: 180899
-
EPR-spectroscopy of reduced oxyferrous-P450cam.
FEBS Lett. 1991 Dec 16;295(1-3):113-5
PMID: 1662641
-
A predictive pattern of computed barriers for C-h hydroxylation by compound I of cytochrome p450.
J Am Chem Soc. 2004 Jul 14;126(27):8362-3
PMID: 15237977
-
P450 BM3: the very model of a modern flavocytochrome.
Trends Biochem Sci. 2002 May;27(5):250-7
PMID: 12076537
-
Oxidation of methoxyphenethylamines by cytochrome P450 2D6. Analysis of rate-limiting steps.
J Biol Chem. 2002 Sep 13;277(37):33711-9
PMID: 12093814
-
Cytochrome P-450--catalyzed formation of delta 4-VPA, a toxic metabolite of valproic acid.
Science. 1987 Feb 20;235(4791):890-3
PMID: 3101178
-
Cytochrome P450 systems--biological variations of electron transport chains.
Biochim Biophys Acta. 2007 Mar;1770(3):330-44
PMID: 16978787
-
Evidence for compound I formation in the reaction of cytochrome P450cam with m-chloroperbenzoic acid.
Biochem Biophys Res Commun. 1994 Jun 30;201(3):1464-9
PMID: 8024592
-
Biosynthesis of Psoralen: Mechanism of a Cytochrome P450 Catalyzed Oxidative Bond Cleavage.
Angew Chem Int Ed Engl. 1999 Feb 1;38(3):400-402
PMID: 29711662
-
Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis.
J Biol Chem. 2007 Jan 5;282(1):542-54
PMID: 17068340
-
Proton transfer at helium temperatures during dioxygen activation by heme monooxygenases.
J Am Chem Soc. 2004 Dec 15;126(49):15960-1
PMID: 15584719
-
A comparison of substrate dynamics in human CYP2E1 and CYP2A6.
Biochem Biophys Res Commun. 2007 Jan 26;352(4):843-9
PMID: 17156750
-
Active site mechanics of liver microsomal cytochrome P-450.
Arch Biochem Biophys. 1986 Apr;246(1):19-32
PMID: 3963820
-
Sodium periodate, sodium chloride, organic hydroperoxides, and H2O2 as hydroxylating agents in steroid hydroxylation reactions catalyzed by partially purified cytochrome P-450.
Biochem Biophys Res Commun. 1975 Sep 2;66(1):209-16
PMID: 240357
-
Stereochemistry and deuterium isotope effects in camphor hydroxylation by the cytochrome P450cam monoxygenase system.
Biochemistry. 1982 Jan 19;21(2):370-7
PMID: 7074020
-
P450-catalyzed in-chain desaturation of valproic acid: isoform selectivity and mechanism of formation of Delta 3-valproic acid generated by baculovirus-expressed CYP3A1.
Arch Biochem Biophys. 1998 Aug 1;356(1):63-70
PMID: 9681992
-
Freeze-quenched iron-oxo intermediates in cytochromes P450.
Biochem Biophys Res Commun. 2005 Dec 9;338(1):355-64
PMID: 16143295
-
Prostacyclin and thromboxane synthases.
J Lipid Mediat Cell Signal. 1995 Oct;12(2-3):243-55
PMID: 8777569
-
Intramolecular isotope effects for benzylic hydroxylation of isomeric xylenes and 4,4'-dimethylbiphenyl by cytochrome P450: relationship between distance of methyl groups and masking of the intrinsic isotope effect.
Biochemistry. 1997 Jun 10;36(23):7136-43
PMID: 9188713
-
Cytochrome P-450-mediated dehydrogenation of 2-n-propyl-2(E)-pentenoic acid, a pharmacologically-active metabolite of valproic acid, in rat liver microsomal preparations.
Drug Metab Dispos. 1993 Mar-Apr;21(2):242-8
PMID: 8097692
-
Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization.
J Biol Chem. 2002 Aug 2;277(31):27725-32
PMID: 12016226
-
Biotransformation of lovastatin. II. In vitro metabolism by rat and mouse liver microsomes and involvement of cytochrome P-450 in dehydrogenation of lovastatin.
Drug Metab Dispos. 1990 Mar-Apr;18(2):218-22
PMID: 1971576
-
Structure and chemistry of cytochrome P450.
Chem Rev. 2005 Jun;105(6):2253-77
PMID: 15941214
-
Possible higher valence states of cytochrome P-450 during oxidative reactions.
Biochem Biophys Res Commun. 1974 Sep 23;60(2):695-702
PMID: 4371068
-
Cytochrome P450-dependent desaturation of lauric acid: isoform selectivity and mechanism of formation of 11-dodecenoic acid.
Chem Biol Interact. 1998 Mar 12;110(1-2):103-21
PMID: 9566728
-
P(450)/NADPH/O(2)- and P(450)/PhIO-catalyzed N-dealkylations are mechanistically distinct.
J Am Chem Soc. 2005 Feb 9;127(5):1376-7
PMID: 15686361
-
Bis-allylic hydroxylation of polyunsaturated fatty acids by hepatic monooxygenases and its relation to the enzymatic and nonenzymatic formation of conjugated hydroxy fatty acids.
Arch Biochem Biophys. 1993 Jan;300(1):434-9
PMID: 8424677
-
What is the active species of cytochrome P450 during camphor hydroxylation? QM/MM studies of different electronic states of compound I and of reduced and oxidized iron-oxo intermediates.
J Am Chem Soc. 2007 Jul 25;129(29):8978-87
PMID: 17595079
-
The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature.
DNA Cell Biol. 1993 Jan-Feb;12(1):1-51
PMID: 7678494
-
Crystal structure of CYP199A2, a para-substituted benzoic acid oxidizing cytochrome P450 from Rhodopseudomonas palustris.
J Mol Biol. 2008 Nov 14;383(3):561-74
PMID: 18762195
-
CYP4 isozyme specificity and the relationship between omega-hydroxylation and terminal desaturation of valproic acid.
Biochemistry. 1995 Jun 20;34(24):7889-95
PMID: 7794900
-
Mechanisms of hydroxylation by cytochrome P-450: exchange of iron-oxygen intermediates with water.
Biochem Biophys Res Commun. 1982 Jan 29;104(2):620-5
PMID: 6803786
-
Intermediates in the reaction of substrate-free cytochrome P450cam with peroxy acetic acid.
FEBS Lett. 2000 Aug 18;479(3):149-54
PMID: 10981725
-
Functional annotation of the Arabidopsis P450 superfamily based on large-scale co-expression analysis.
Biochem Soc Trans. 2006 Dec;34(Pt 6):1192-8
PMID: 17073783
-
The involvement of cytochrome P-450 in hepatic microsomal steroid hydroxylation reactions supported by sodium periodate, sodium chlorite, and organic hydroperoxides.
Eur J Biochem. 1976 Jan 2;61(1):43-52
PMID: 173555
-
CYP119 plus a Sulfolobus tokodaii strain 7 ferredoxin and 2-oxoacid:ferredoxin oxidoreductase constitute a high-temperature cytochrome P450 catalytic system.
J Am Chem Soc. 2002 Oct 30;124(43):12682-3
PMID: 12392414
-
Crystal structure of human cytochrome P450 2D6.
J Biol Chem. 2006 Mar 17;281(11):7614-22
PMID: 16352597
-
Cytochrome P450cam: crystallography, oxygen activation, and electron transfer.
FASEB J. 1992 Jan 6;6(2):674-9
PMID: 1537455
-
The catalytic pathway of cytochrome p450cam at atomic resolution.
Science. 2000 Mar 3;287(5458):1615-22
PMID: 10698731
-
Enantiotopic differentiation during the biotransformation of valproic acid to the hepatotoxic olefin 2-n-propyl-4-pentenoic acid.
Chem Res Toxicol. 1989 Jan-Feb;2(1):35-40
PMID: 2519229
-
Resonance Raman detection of the hydroperoxo intermediate in the cytochrome P450 enzymatic cycle.
J Am Chem Soc. 2007 May 23;129(20):6382-3
PMID: 17461587
-
The influence of substrate on the spectral properties of oxyferrous wild-type and T252A cytochrome P450-CAM.
Arch Biochem Biophys. 2005 Apr 1;436(1):40-9
PMID: 15752707
-
Cytochrome P450cam and its complexes. Mössbauer parameters of the heme iron.
Biochim Biophys Acta. 1976 Jan 20;420(1):8-26
PMID: 2296
-
Structure and direct electrochemistry of cytochrome P450 from the thermoacidophilic crenarchaeon, Sulfolobus tokodaii strain 7.
J Inorg Biochem. 2004 Jul;98(7):1194-9
PMID: 15219985
-
Laboratory evolution of P450 BM3 for mediated electron transfer yielding an activity-improved and reductase-independent variant.
Protein Eng Des Sel. 2008 Jan;21(1):29-35
PMID: 18093991
-
Isotope effect studies on the mechanism of the cytochrome P-450IIA1-catalyzed formation of delta 6-testosterone from testosterone.
Drug Metab Dispos. 1990 Nov-Dec;18(6):974-9
PMID: 1981547
-
Thermophilic cytochrome P450 (CYP119) from Sulfolobus solfataricus: high resolution structure and functional properties.
J Inorg Biochem. 2002 Sep 20;91(4):491-501
PMID: 12237217
-
Characterization of the oxygenated intermediate of the thermophilic cytochrome P450 CYP119.
J Inorg Biochem. 2001 Dec 15;87(4):215-26
PMID: 11744059
-
Theoretical calculations of carbon-oxygen bond dissociation enthalpies of peroxyl radicals formed in the autoxidation of lipids.
J Am Chem Soc. 2003 May 14;125(19):5801-10
PMID: 12733921
-
Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations.
Biochemistry. 1979 Mar 6;18(5):865-70
PMID: 420819
-
Prediction of activation energies for hydrogen abstraction by cytochrome p450.
J Med Chem. 2006 Nov 2;49(22):6489-99
PMID: 17064067
-
Crystal structure and properties of CYP231A2 from the thermoacidophilic archaeon Picrophilus torridus.
Biochemistry. 2008 Feb 19;47(7):2071-9
PMID: 18197710
-
Functional genomics of P450s.
Annu Rev Plant Biol. 2003;54:629-67
PMID: 14503006
-
Identification and characterization of two functional domains in cytochrome P-450BM-3, a catalytically self-sufficient monooxygenase induced by barbiturates in Bacillus megaterium.
J Biol Chem. 1987 May 15;262(14):6683-90
PMID: 3106360
-
A self-sufficient cytochrome p450 with a primary structural organization that includes a flavin domain and a [2Fe-2S] redox center.
J Biol Chem. 2003 Dec 5;278(49):48914-20
PMID: 14514666
-
Hydroxylation of aliphatic compounds by liver microsomes. I. The distribution pattern of isomeric alcohols.
Hoppe Seylers Z Physiol Chem. 1970 Aug;351(8):903-12
PMID: 4393760
-
Crystal structure of a thermophilic cytochrome P450 from the archaeon Sulfolobus solfataricus.
J Biol Chem. 2000 Oct 6;275(40):31086-92
PMID: 10859321
-
Tyrosine radical formation in the reaction of wild type and mutant cytochrome P450cam with peroxy acids: a multifrequency EPR study of intermediates on the millisecond time scale.
J Biol Chem. 2004 Mar 19;279(12):10919-30
PMID: 14688245
-
Two univalent electron transfers from putidaredoxin to bacterial cytochrome P450 at subzero temperature.
Biochemistry. 1978 Jul 11;17(14):2835-9
PMID: 687565
-
On the mechanism of action of cytochrome P-450. Role of peroxy spectral intermediates in substrate hydroxylation.
J Biol Chem. 1981 Jun 10;256(11):5755-63
PMID: 7240170
-
Substrate recognition and molecular mechanism of fatty acid hydroxylation by cytochrome P450 from Bacillus subtilis. Crystallographic, spectroscopic, and mutational studies.
J Biol Chem. 2003 Mar 14;278(11):9761-7
PMID: 12519760
-
Substrate modulates compound I formation in peroxide shunt pathway of Pseudomonas putida cytochrome P450(cam).
Biochem Biophys Res Commun. 2004 Feb 6;314(2):610-4
PMID: 14733951
-
The Sulfolobus solfataricus electron donor partners of thermophilic CYP119: an unusual non-NAD(P)H-dependent cytochrome P450 system.
Arch Biochem Biophys. 2005 Feb 1;434(1):169-77
PMID: 15629120
-
Enzymatic reaction of hydrogen peroxide-dependent peroxygenase cytochrome P450s: kinetic deuterium isotope effects and analyses by resonance Raman spectroscopy.
Biochemistry. 2002 Feb 12;41(6):1886-92
PMID: 11827534
-
Stereochemical dynamics of aliphatic hydroxylation by cytochrome P-450.
J Am Chem Soc. 1986 Sep 1;108(19):6024-31
PMID: 22175367
-
Spectroscopic studies of peroxyacetic acid reaction intermediates of cytochrome P450cam and chloroperoxidase.
J Inorg Biochem. 2002 Sep 20;91(4):586-96
PMID: 12237224
-
State-of-the-art tools for computational site of metabolism predictions: comparative analysis, mechanistical insights, and future applications.
Drug Metab Rev. 2007;39(1):61-86
PMID: 17364881
-
Electron transfer by diflavin reductases.
Biochim Biophys Acta. 2004 Apr 8;1698(1):1-26
PMID: 15063311
-
Cytochrome p450 compound I.
J Am Chem Soc. 2006 Apr 12;128(14):4580-1
PMID: 16594688
-
Cytochrome P450 3A4-catalyzed testosterone 6beta-hydroxylation stereochemistry, kinetic deuterium isotope effects, and rate-limiting steps.
J Biol Chem. 2005 May 20;280(20):19496-506
PMID: 15772082
-
Hydroxylation of camphor by reduced oxy-cytochrome P450cam: mechanistic implications of EPR and ENDOR studies of catalytic intermediates in native and mutant enzymes.
J Am Chem Soc. 2001 Feb 21;123(7):1403-15
PMID: 11456714
-
Thermophilic cytochrome P450 enzymes.
Biochem Biophys Res Commun. 2005 Dec 9;338(1):437-45
PMID: 16139791
-
The ferrous-oxy complex of human aromatase.
Biochem Biophys Res Commun. 2008 Jul 25;372(2):379-82
PMID: 18482580
-
Rational design of a minimal and highly enriched CYP102A1 mutant library with improved regio-, stereo- and chemoselectivity.
Chembiochem. 2009 Mar 23;10(5):853-61
PMID: 19222039
-
Bond dissociation energies of organic molecules.
Acc Chem Res. 2003 Apr;36(4):255-63
PMID: 12693923
-
Photochemical generation of a highly reactive iron-oxo intermediate. A true iron(V)-oxo species?
J Am Chem Soc. 2005 Oct 12;127(40):13776-7
PMID: 16201783
-
Highly reactive porphyrin-iron-oxo derivatives produced by photolyses of metastable porphyrin-iron(IV) diperchlorates.
J Am Chem Soc. 2009 Feb 25;131(7):2621-8
PMID: 19193008
-
Quantitative structure-activity relationships of cytochrome P-450.
Drug Metab Rev. 1993;25(1-2):1-48
PMID: 8449144
-
Replacement of tyrosine residues by phenylalanine in cytochrome P450cam alters the formation of Cpd II-like species in reactions with artificial oxidants.
J Biol Inorg Chem. 2008 May;13(4):599-611
PMID: 18273651
-
Absorption spectra of cytochrome P450CAM in the reaction with peroxy acids.
FEBS Lett. 1983 Jun 13;156(2):244-8
PMID: 6852258
-
X-ray absorption spectroscopic characterization of a cytochrome P450 compound II derivative.
Proc Natl Acad Sci U S A. 2008 Jun 17;105(24):8179-84
PMID: 18174331
-
Kinetic isotope effects in hydroxylation reactions effected by cytochrome P450 compounds I implicate multiple electrophilic oxidants for P450-catalyzed oxidations.
Biochemistry. 2009 Feb 24;48(7):1620-7
PMID: 19182902
-
The crystal structure of chloroperoxidase: a heme peroxidase--cytochrome P450 functional hybrid.
Structure. 1995 Dec 15;3(12):1367-77
PMID: 8747463
-
Evaluation of norcarane as a probe for radicals in cytochome p450- and soluble methane monooxygenase-catalyzed hydroxylation reactions.
J Am Chem Soc. 2002 Jun 19;124(24):6879-86
PMID: 12059209
-
Reaction of ferric cytochrome P450cam with peracids: kinetic characterization of intermediates on the reaction pathway.
J Biol Chem. 2005 May 27;280(21):20300-9
PMID: 15781454
-
Reaction of cytochrome P450BM3 and peroxynitrite yields nitrosyl complex.
J Am Chem Soc. 2007 May 9;129(18):5855-9
PMID: 17432853
-
Detoxification of alpha- and beta-Thujones (the active ingredients of absinthe): site specificity and species differences in cytochrome P450 oxidation in vitro and in vivo.
Chem Res Toxicol. 2001 May;14(5):589-95
PMID: 11368559
-
Spectra and kinetic studies of the compound I derivative of cytochrome P450 119.
J Am Chem Soc. 2008 Oct 8;130(40):13310-20
PMID: 18788736
-
Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate.
Biochem Biophys Res Commun. 1978 Mar 15;81(1):154-60
PMID: 656092
-
Substrate modulation of the properties and reactivity of the oxy-ferrous and hydroperoxo-ferric intermediates of cytochrome P450cam as shown by cryoreduction-EPR/ENDOR spectroscopy.
J Am Chem Soc. 2005 Feb 9;127(5):1403-13
PMID: 15686372
-
Cytochrome P-450-catalyzed desaturation of valproic acid in vitro. Species differences, induction effects, and mechanistic studies.
J Biol Chem. 1988 Sep 25;263(27):13733-8
PMID: 3138238
-
Protein engineering of oxygenases for biocatalysis.
Curr Opin Chem Biol. 2002 Apr;6(2):130-5
PMID: 12038995
-
Chloroperoxidase. II. Utilization of halogen anions.
J Biol Chem. 1966 Apr 25;241(8):1769-77
PMID: 5945851
-
Alteration of P450 distal pocket solvent leads to impaired proton delivery and changes in heme geometry.
Biochemistry. 2007 Dec 11;46(49):14129-40
PMID: 18001135
-
Formation of compound I by photo-oxidation of compound II.
Org Lett. 2005 Mar 17;7(6):1193-5
PMID: 15760172
-
Engineered alkane-hydroxylating cytochrome P450(BM3) exhibiting nativelike catalytic properties.
Angew Chem Int Ed Engl. 2007;46(44):8414-8
PMID: 17886313
-
Cryoradiolytic reduction of crystalline heme proteins: analysis by UV-Vis spectroscopy and X-ray crystallography.
J Synchrotron Radiat. 2007 Jan;14(Pt 1):11-23
PMID: 17211068
-
Structural biology and biochemistry of cytochrome P450 systems in Mycobacterium tuberculosis.
Drug Metab Rev. 2008;40(3):427-46
PMID: 18642141
-
Isolation and functional characterization of CYP71AJ4 encoding for the first P450 monooxygenase of angular furanocoumarin biosynthesis.
J Biol Chem. 2009 Feb 20;284(8):4776-85
PMID: 19098286
-
Kinetics of oxidation of benzphetamine by compounds I of cytochrome P450 2B4 and its mutants.
J Am Chem Soc. 2009 Mar 4;131(8):2971-6
PMID: 19209859
-
Quantum and molecular mechanical study of the first proton transfer in the catalytic cycle of cytochrome P450cam and its mutant D251N.
J Phys Chem B. 2008 Apr 24;112(16):5126-38
PMID: 18386859
-
Photochemical production of a highly reactive porphyrin-iron-oxo species.
Inorg Chem. 2007 Mar 5;46(5):1517-9
PMID: 17284026
-
Mechanism of cytochrome P4503A4- and 2D6-catalyzed dehydrogenation of ezlopitant as probed with isotope effects using five deuterated analogs.
Drug Metab Dispos. 2001 Dec;29(12):1599-607
PMID: 11717179
-
Cytochrome P-450-butyl peroxide complex detected by ESR.
Biochem Biophys Res Commun. 1993 Feb 26;191(1):157-64
PMID: 8383486
-
Peroxynitrite reactivity with amino acids and proteins.
Amino Acids. 2003 Dec;25(3-4):295-311
PMID: 14661092
-
The ferrous-dioxygen intermediate in human cytochrome P450 3A4. Substrate dependence of formation and decay kinetics.
J Biol Chem. 2006 Aug 18;281(33):23313-8
PMID: 16762915
-
On the ability of cumene hydroperoxide and NaIO4 to support microsomal hydroxylations in biosynthesis and metabolism of bile acids.
FEBS Lett. 1976 Jul 15;66(2):299-302
PMID: 8336
-
Cryotrapped reaction intermediates of cytochrome p450 studied by radiolytic reduction with phosphorus-32.
J Biol Chem. 2001 Apr 13;276(15):11648-52
PMID: 11152470
-
Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane.
J Am Chem Soc. 2002 May 29;124(21):6020-7
PMID: 12022835
-
Complex reactions catalyzed by cytochrome P450 enzymes.
Biochim Biophys Acta. 2007 Mar;1770(3):314-29
PMID: 17239540
-
Multiple-ligand binding in CYP2A6: probing mechanisms of cytochrome P450 cooperativity by assessing substrate dynamics.
Biochemistry. 2008 Mar 4;47(9):2978-88
PMID: 18247580
-
Crystallographic study on the dioxygen complex of wild-type and mutant cytochrome P450cam. Implications for the dioxygen activation mechanism.
J Biol Chem. 2005 Sep 9;280(36):31659-63
PMID: 15994329
-
Cyclopropyl containing fatty acids as mechanistic probes for cytochromes P450.
J Org Chem. 2005 Apr 1;70(7):2455-69
PMID: 15787531
-
Multiple mechanisms of cytochrome P450-catalyzed substrate hydroxylations.
Biochem Biophys Res Commun. 1981 Mar 31;99(2):530-5
PMID: 7236281
-
Preliminary characterization and crystal structure of a thermostable cytochrome P450 from Thermus thermophilus.
J Biol Chem. 2003 Jan 3;278(1):608-16
PMID: 12401810
-
Compound lipophilicity for substrate binding to human P450s in drug metabolism.
Drug Discov Today. 2004 Jun 15;9(12):530-7
PMID: 15183161