ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Theory for the observed isotope effects from enzymic systems that form multiple products via branched reaction pathways: cytochrome P-450

Cite this: Biochemistry 1989, 28, 23, 9012–9018
Publication Date (Print):November 14, 1989
https://doi.org/10.1021/bi00449a009
    ACS Legacy Archive

    Article Views

    180

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 44 publications.

    1. Li Chen, Nathchar Naowarojna, Bin Chen, Meiling Xu, Melissa Quill, Jiangyun Wang, Zixin Deng, Changming Zhao, Pinghua Liu. Mechanistic Studies of a Nonheme Iron Enzyme OvoA in Ovothiol Biosynthesis Using a Tyrosine Analogue, 2-Amino-3-(4-hydroxy-3-(methoxyl) phenyl) Propanoic Acid (MeOTyr). ACS Catalysis 2019, 9 (1) , 253-258. https://doi.org/10.1021/acscatal.8b03903
    2. Li Chen, Nathchar Naowarojna, Heng Song, Shu Wang, Jiangyun Wang, Zixin Deng, Changming Zhao, Pinghua Liu. Use of a Tyrosine Analogue To Modulate the Two Activities of a Nonheme Iron Enzyme OvoA in Ovothiol Biosynthesis, Cysteine Oxidation versus Oxidative C–S Bond Formation. Journal of the American Chemical Society 2018, 140 (13) , 4604-4612. https://doi.org/10.1021/jacs.7b13628
    3. Jonathan D. Tyzack, Peter A. Hunt, and Matthew D. Segall . Predicting Regioselectivity and Lability of Cytochrome P450 Metabolism Using Quantum Mechanical Simulations. Journal of Chemical Information and Modeling 2016, 56 (11) , 2180-2193. https://doi.org/10.1021/acs.jcim.6b00233
    4. W. Kurtis Childers and John P. Harrelson . Allosteric Modulation of Substrate Motion in Cytochrome P450 3A4-Mediated Xylene Oxidation. Biochemistry 2014, 53 (6) , 1018-1028. https://doi.org/10.1021/bi401472p
    5. Dhara D. Shah, John A. Conrad, and Graham R. Moran . Intermediate Partitioning Kinetic Isotope Effects for the NIH Shift of 4-Hydroxyphenylpyruvate Dioxygenase and the Hydroxylation Reaction of Hydroxymandelate Synthase Reveal Mechanistic Complexity. Biochemistry 2013, 52 (35) , 6097-6107. https://doi.org/10.1021/bi400534q
    6. Francis K. Yoshimoto, Yishan Zhou, Hwei-Ming Peng, David Stidd, Jennifer A. Yoshimoto, Kamalesh K. Sharma, Susan Matthew, and Richard J. Auchus . Minor Activities and Transition State Properties of the Human Steroid Hydroxylases Cytochromes P450c17 and P450c21, from Reactions Observed with Deuterium-Labeled Substrates. Biochemistry 2012, 51 (36) , 7064-7077. https://doi.org/10.1021/bi300895w
    7. Dhara D. Shah, John A. Conrad, Brian Heinz, June M. Brownlee, and Graham R. Moran . Evidence for the Mechanism of Hydroxylation by 4-Hydroxyphenylpyruvate Dioxygenase and Hydroxymandelate Synthase from Intermediate Partitioning in Active Site Variants. Biochemistry 2011, 50 (35) , 7694-7704. https://doi.org/10.1021/bi2009344
    8. Stefan Balaz. Modeling Kinetics of Subcellular Disposition of Chemicals. Chemical Reviews 2009, 109 (5) , 1793-1899. https://doi.org/10.1021/cr030440j
    9. Kevin Francis and Giovanni Gadda. Inflated Kinetic Isotope Effects in the Branched Mechanism of Neurospora crassa 2-Nitropropane Dioxygenase. Biochemistry 2009, 48 (11) , 2403-2410. https://doi.org/10.1021/bi802238j
    10. John P. Harrelson, William M. Atkins and Sidney D. Nelson. Multiple-Ligand Binding in CYP2A6: Probing Mechanisms of Cytochrome P450 Cooperativity by Assessing Substrate Dynamics. Biochemistry 2008, 47 (9) , 2978-2988. https://doi.org/10.1021/bi702020y
    11. K. R. Korzekwa,, N. Krishnamachary,, M. Shou,, A. Ogai,, R. A. Parise,, A. E. Rettie,, F. J. Gonzalez, and, T. S. Tracy. Evaluation of Atypical Cytochrome P450 Kinetics with Two-Substrate Models:  Evidence That Multiple Substrates Can Simultaneously Bind to Cytochrome P450 Active Sites. Biochemistry 1998, 37 (12) , 4137-4147. https://doi.org/10.1021/bi9715627
    12. Jeffrey K. Atkinson, Paul F. Hollenberg, K. U. Ingold, Cathy C. Johnson, Marie-Helene Le Tadic, Martin Newcomb, and David A. Putt. Cytochrome P450-Catalyzed Hydroxylation of Hydrocarbons: Kinetic Deuterium Isotope Effects for the Hydroxylation of an Ultrafast Radical Clock. Biochemistry 1994, 33 (35) , 10630-10637. https://doi.org/10.1021/bi00201a009
    13. James R. Gillette, John F. Darbyshire, and Katsumi Sugiyama. Theory for the observed isotope effects on the formation of multiple products by different kinetic mechanisms of cytochrome P450 enzymes. Biochemistry 1994, 33 (10) , 2927-2937. https://doi.org/10.1021/bi00176a024
    14. Scott P. Salowe, Walter J. Krol, Dirk Iwata-Reuyl, and Craig A. Townsend. Elucidation of the order of oxidations and identification of an intermediate in the multistep clavaminate synthase reaction. Biochemistry 1991, 30 (8) , 2281-2292. https://doi.org/10.1021/bi00222a034
    15. Mohamed W. Attwa, Gamal A. E. Mostafa, Haitham AlRabiah, Adnan A. Kadi. An LC–MS/MS Analytical Method for Quantifying Tepotinib in Human Liver Microsomes: Application to In Vitro and In Silico Metabolic Stability Estimation. Separations 2023, 10 (6) , 330. https://doi.org/10.3390/separations10060330
    16. Phan T. Truong, Sophia G. Miller, Emily J. McLaughlin Sta. Maria, Miriam A. Bowring. Large Isotope Effects in Organometallic Chemistry. Chemistry – A European Journal 2021, 27 (60) , 14800-14815. https://doi.org/10.1002/chem.202102189
    17. Ken Korzekwa. Enzyme Kinetics of Oxidative Metabolism—Cytochromes P450. 2021, 237-256. https://doi.org/10.1007/978-1-0716-1554-6_9
    18. Wondemagegn Hailemichael Wanna, Ravirala Ramu, Damodar Janmanchi, Yi-Fang Tsai, Natarajan Thiyagarajan, Steve S.-F. Yu. An efficient and recyclable copper nano-catalyst for the selective oxidation of benzene to p-benzoquinone (p-BQ) using H2O2(aq) in CH3CN. Journal of Catalysis 2019, 370 , 332-346. https://doi.org/10.1016/j.jcat.2019.01.005
    19. Heng Song, Nathchar Naowarojna, Ronghai Cheng, Juan Lopez, Pinghua Liu. Non-heme iron enzyme-catalyzed complex transformations. 2019, 1-61. https://doi.org/10.1016/bs.apcsb.2019.06.002
    20. Ravirala Ramu, Wondemagegn Hailemichael Wanna, Damodar Janmanchi, Yi-Fang Tsai, Chih-Cheng Liu, Chung-Yuan Mou, Steve S.-F. Yu. Mechanistic study for the selective oxidation of benzene and toluene catalyzed by Fe(ClO4)2 in an H2O2-H2O-CH3CN system. Molecular Catalysis 2017, 441 , 114-121. https://doi.org/10.1016/j.mcat.2017.08.006
    21. Scott L. Harbeson, Adam J. Morgan, Julie F. Liu, Ara M. Aslanian, Sophia Nguyen, Gary W. Bridson, Christopher L. Brummel, Lijun Wu, Roger D. Tung, Lana Pilja, Virginia Braman, Vinita Uttamsingh. Altering Metabolic Profiles of Drugs by Precision Deuteration 2: Discovery of a Deuterated Analog of Ivacaftor with Differentiated Pharmacokinetics for Clinical Development. Journal of Pharmacology and Experimental Therapeutics 2017, 362 (2) , 359-367. https://doi.org/10.1124/jpet.117.241497
    22. Julie F. Liu, Scott L. Harbeson, Christopher L. Brummel, Roger Tung, Robert Silverman, Dario Doller. A Decade of Deuteration in Medicinal Chemistry. 2017, 519-542. https://doi.org/10.1016/bs.armc.2017.08.010
    23. Francis K. Yoshimoto, Richard J. Auchus. The diverse chemistry of cytochrome P450 17A1 (P450c17, CYP17A1). The Journal of Steroid Biochemistry and Molecular Biology 2015, 151 , 52-65. https://doi.org/10.1016/j.jsbmb.2014.11.026
    24. John Eksterowicz, Dan A. Rock, Brooke M. Rock, Larry C. Wienkers, Robert S. Foti. Characterization of the Active Site Properties of CYP4F12. Drug Metabolism and Disposition 2014, 42 (10) , 1698-1707. https://doi.org/10.1124/dmd.114.059626
    25. F. Peter Guengerich. Kinetic deuterium isotope effects in cytochrome P450 oxidation reactions. Journal of Labelled Compounds and Radiopharmaceuticals 2013, 56 (9-10) , 428-431. https://doi.org/10.1002/jlcr.3031
    26. . Oxidation Pathways and the Enzymes That Mediate Them. 2007, 33-108. https://doi.org/10.1201/b14488-5
    27. W.F. Trager. Principles of Drug Metabolism 1: Redox Reactions. 2007, 87-132. https://doi.org/10.1016/B0-08-045044-X/00119-X
    28. John P. Harrelson, Kirk R. Henne, Darwin O.V. Alonso, Sidney D. Nelson. A comparison of substrate dynamics in human CYP2E1 and CYP2A6. Biochemical and Biophysical Research Communications 2007, 352 (4) , 843-849. https://doi.org/10.1016/j.bbrc.2006.11.071
    29. Paul Fitzpatrick. Isotope Effects from Partitioning of Intermediates in Enzyme-Catalyzed Hydroxylation Reactions. 2005, 861-874. https://doi.org/10.1201/9781420028027.ch34
    30. William M. Atkins. NON-MICHAELIS-MENTEN KINETICS IN CYTOCHROME P450-CATALYZED REACTIONS. Annual Review of Pharmacology and Toxicology 2005, 45 (1) , 291-310. https://doi.org/10.1146/annurev.pharmtox.45.120403.100004
    31. Joel A. Krauser, F. Peter Guengerich. Cytochrome P450 3A4-catalyzed Testosterone 6β-Hydroxylation Stereochemistry, Kinetic Deuterium Isotope Effects, and Rate-limiting Steps. Journal of Biological Chemistry 2005, 280 (20) , 19496-19506. https://doi.org/10.1074/jbc.M501854200
    32. Sidney D. Nelson, William F. Trager. THE USE OF DEUTERIUM ISOTOPE EFFECTS TO PROBE THE ACTIVE SITE PROPERTIES, MECHANISM OF CYTOCHROME P450-CATALYZED REACTIONS, AND MECHANISMS OF METABOLICALLY DEPENDENT TOXICITY. Drug Metabolism and Disposition 2003, 31 (12) , 1481-1497. https://doi.org/10.1124/dmd.31.12.1481
    33. Alfin Vaz. Dioxygen Activation by Cytochromes P450. 2003, 1-32. https://doi.org/10.1201/9781420028485.ch1
    34. Kevin H. Mitchell, Corina E. Rogge, Todd Gierahn, Brian G. Fox. Insight into the mechanism of aromatic hydroxylation by toluene 4-monooxygenase by use of specifically deuterated toluene and p- xylene. Proceedings of the National Academy of Sciences 2003, 100 (7) , 3784-3789. https://doi.org/10.1073/pnas.0636619100
    35. Michael L. Schrag, Larry C. Wienkers. Triazolam Substrate Inhibition. 2001, 347-350. https://doi.org/10.1007/978-1-4615-0667-6_56
    36. STEVEN A. WRIGHTON, ERIN G. SCHUETZ, KENNETH E. THUMMEL, DANNY D. SHEN, KENNETH R. KORZEKWA, PAUL B. WATKINS. THE HUMAN CYP3A SUBFAMILY: PRACTICAL CONSIDERATIONS*. Drug Metabolism Reviews 2000, 32 (3-4) , 339-361. https://doi.org/10.1081/DMR-100102338
    37. L. Chastine Bell, F. Peter Guengerich. Oxidation Kinetics of Ethanol by Human Cytochrome P450 2E1. Journal of Biological Chemistry 1997, 272 (47) , 29643-29651. https://doi.org/10.1074/jbc.272.47.29643
    38. Y. Benchekroun, S. Dautraix, M. Desage, J. L. Brazier. Deuterium isotope effects on caffeine metabolism. European Journal of Drug Metabolism and Pharmacokinetics 1997, 22 (2) , 127-133. https://doi.org/10.1007/BF03189795
    39. Kenneth R. Korzekwa, James Grogan, Steven DeVito, Jeffrey P. Jones. Electronic Models for Cytochrome P450 Oxidations. 1996, 361-369. https://doi.org/10.1007/978-1-4757-9480-9_44
    40. James R. Gillette. Keynote Address: Man, Mice, Microsomes, Metabolites, and Mathematics 40 Years after the Revolution. Drug Metabolism Reviews 1995, 27 (1-2) , 1-44. https://doi.org/10.3109/03602539509029813
    41. Kenneth r. Korzekwa, James r. Gillette, William f. Trager. Isotope Effect Studies on the Cytochrome P450 Enzymes. Drug Metabolism Reviews 1995, 27 (1-2) , 45-59. https://doi.org/10.3109/03602539509029814
    42. J.S. Marchini, L. Castillo, T.E. Chapman, J.A. Vogt, A. Ajami, V.R. Young. Phenylalanine conversion to tyrosine: Comparative determination with l-[ring-2H5]phenylalanine and l-[1-13C]phenylalanine as tracers in man. Metabolism 1993, 42 (10) , 1316-1322. https://doi.org/10.1016/0026-0495(93)90131-7
    43. N. Hanioka, F.J. Gonzalez, N.A. Lindberg, G. Liu, K.R. Korzekwa. Chimeric cDNA expression and site directed mutagenesis studies of cytochrome P450s CYP2A1 and CYP2A2. The Journal of Steroid Biochemistry and Molecular Biology 1992, 43 (8) , 1037-1043. https://doi.org/10.1016/0960-0760(92)90331-C
    44. Craig A Townsend, Amit Basak. Experiments and speculations on the role of oxidative cyclization chemistry in natural product biosynthesis. Tetrahedron 1991, 47 (14-15) , 2591-2602. https://doi.org/10.1016/S0040-4020(01)81792-0

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect