ArticleJournal of the American Chemical Society2014
Mechanism of the third oxidative step in the conversion of androgens to estrogens by cytochrome P450 19A1 steroid aromatase.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.
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Who cites it
48 citing papers in PubMed.
- Macrocyclic geminal diols: synthesis, structures, stability and photophysical properties.Chemical science · 2026Article
- Mass Spectral Analysis of Sterols and Other Steroids in Different Ionization Modes: Sensitivity and Oxidation Artifacts.Journal of the American Society for Mass Spectrometry · 2025Article
- Article
- Regioselective Synthesis of Potential Non-Quinonoid Prodrugs of Plasmodione: Antiparasitic Properties Against Two Hemoglobin-Feeding Parasites and Drug Metabolism Studies.Molecules (Basel, Switzerland) · 2024Article
- Updates on Mechanisms of Cytochrome P450 Catalysis of Complex Steroid Oxidations.International journal of molecular sciences · 2024Review
- Roles of Ferric Peroxide Anion Intermediates (FeAngewandte Chemie (International ed. in English) · 2024Article
- Expression characteristics of the cyp19a1b aromatase gene and its response to 17β-estradiol treatment in largemouth bass (Micropterus salmoides).Fish physiology and biochemistry · 2024Article
- Functional Model of Compound II of Cytochrome P450: Spectroscopic Characterization and Reactivity Studies of a FeJACS Au · 2024Article
- Oxygen-18 Labeling Reveals a Mixed Fe-O Mechanism in the Last Step of Cytochrome P450 51 Sterol 14α-Demethylation.Angewandte Chemie (International ed. in English) · 2024Article
- Oxygen-18 Labeling Defines a Ferric Peroxide (Compound 0) Mechanism in the Oxidative Deformylation of Aldehydes by Cytochrome P450 2B4.ACS catalysis · 2024Article
- Ninety-eight semesters of cytochrome P450 enzymes and related topics-What have I taught and learned?The Journal of biological chemistry · 2024Article
- Cofactorless oxygenases guide anthraquinone-fused enediyne biosynthesis.Nature chemical biology · 2024Article
- <sc>d</sc>-Chiro-Inositol in Clinical Practice: A Perspective from the Experts Group on Inositol in Basic and Clinical Research (EGOI).Gynecologic and obstetric investigation · 2024Review
- Sex differences in distribution and identity of aromatase gene expressing cells in the young adult rat brain.Biology of sex differences · 2023Article
- Depicting the proton relay network in human aromatase: New insights into the role of the alcohol-acid pair.Protein science : a publication of the Protein Society · 2022Article
- Diverse reactions catalyzed by cytochrome P450 and biosynthesis of steroid hormone.Biophysics and physicobiology · 2022Article
- Lipopolysaccharide alters CEBPβ signaling and reduces estradiol production in bovine granulosa cells.CABI agriculture and bioscience · 2022Article
- Roles of cytochrome P450 enzymes in pharmacology and toxicology: Past, present, and future.Advances in pharmacology (San Diego, Calif.) · 2022Article
- 19-hydroxy Steroids in the Aromatase Reaction: Review on Expression and Potential Functions.Journal of the Endocrine Society · 2021Review
- Mechanisms of allosteric and mixed mode aromatase inhibitors.RSC chemical biology · 2021Article
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2 authors.
Funding
Abstract
Aromatase is the cytochrome P450 enzyme that cleaves the C10-C19 carbon-carbon bond of androgens to form estrogens, in a three-step process. Compound I (FeO(3+)) and ferric peroxide (FeO2(-)) have both been proposed in the literature as the active iron species in the third step, yielding an estrogen and formic acid. Incubation of purified aromatase with its 19-deutero-19-oxo androgen substrate was performed in the presence of (18)O2, and the products were derivatized using a novel diazo reagent. Analysis of the products by high-resolution mass spectrometry showed a lack of (18)O incorporation in the product formic acid, supporting only the Compound I pathway. Furthermore, a new androgen 19-carboxylic acid product was identified. The rates of nonenzymatic hydration of the 19-oxo androgen and dehydration of the 19,19-gem-diol were shown to be catalytically competent. Thus, the evidence supports Compound I and not ferric peroxide as the active iron species in the third step of the steroid aromatase reaction.
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