ArticleJournal of the American Chemical Society2022
Enzymatic Control over Reactive Intermediates Enables Direct Oxidation of Alkenes to Carbonyls by a P450 Iron-Oxo Species.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Promiscuous fungal peroxygenase fromiScience · 2026Article
- On the Origin of Substrate Specificity of Enzymes from the Amidohydrolase Superfamily.Angewandte Chemie (International ed. in English) · 2026Article
- Bimolecular Homolytic Substitution (SACS central science · 2025Review
- Uncatalyzed aerobic epoxidation of liquid alkyl alkenes.Nature communications · 2025Article
- Iron Porphyrins and Iron Salens as Highly Enantioselective Catalysts for the Ring-Expansion Reaction of Epoxides to Tetrahydrofurans.Organic letters · 2025Article
- Discovery of iron-oxo-catalyzed oxidation of fluorophenyl systems to carbonyls or epoxides: reactive intermediates determined mechanism.Journal of molecular modeling · 2025Article
- QM/MM Study of the Reaction Mechanism of L-Tyrosine Hydroxylation Catalyzed by the Enzyme CYP76AD1.The journal of physical chemistry. B · 2024Article
- Mechanism of the Oxidative Ring-Closure Reaction during Gliotoxin Biosynthesis by Cytochrome P450 GliF.International journal of molecular sciences · 2024Article
- Stereodivergent photobiocatalytic radical cyclization through the repurposing and directed evolution of fatty acid photodecarboxylases.Nature chemistry · 2024Article
- Review
- Radical and Cationic Pathways in C(Journal of the American Chemical Society · 2023Article
- Cytochrome P450 Mediated Cyclization in Eunicellane Derived Diterpenoid Biosynthesis.Angewandte Chemie (International ed. in English) · 2023Article
- Sustainable Wacker-Type Oxidations.Angewandte Chemie (International ed. in English) · 2022Review
- Engineered P450 Atom-Transfer Radical Cyclases are Bifunctional Biocatalysts: Reaction Mechanism and Origin of Enantioselectivity.Journal of the American Chemical Society · 2022Article
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5 authors.
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Abstract
The aerobic oxidation of alkenes to carbonyls is an important and challenging transformation in synthesis. Recently, a new P450-based enzyme (aMOx) has been evolved in the laboratory to directly oxidize styrenes to their corresponding aldehydes with high activity and selectivity. The enzyme utilizes a heme-based, high-valent iron-oxo species as a catalytic oxidant that normally epoxidizes alkenes, similar to other catalysts. How the evolved aMOx enzyme suppresses the commonly preferred epoxidation and catalyzes direct carbonyl formation is currently not well understood. Here, we combine computational modelling together with mechanistic experiments to study the reaction mechanism and unravel the molecular basis behind the selectivity achieved by aMOx. Our results describe that although both pathways are energetically accessible diverging from a common covalent radical intermediate, intrinsic
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