ArticleProceedings of the National Academy of Sciences of the United States of America2016
Catalytic strategy for carbon-carbon bond scission by the cytochrome P450 OleT.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed, 98 citations in OpenAlex.
- Temperature-dependent conformational dynamics govern regioselectivity in a CYP152 decarboxylase.The Journal of biological chemistry · 2026Article
- Metabolic Stability of Fluorinated Small Molecules: A Physical Organic Chemistry Perspective.Journal of medicinal chemistry · 2026Review
- Regulation of ferryl reactivity by the cytochrome P450 decarboxylase OleT.Journal of inorganic biochemistry · 2025Article
- Coordinated conformational changes in P450 decarboxylases enable hydrocarbons production from renewable feedstocks.Nature communications · 2025Article
- In Vitro Characterization of Kitasetaline Biosynthesis Reveals a Bifunctional P450 Decarboxylase and a Vinyl β-Carboline Intermediate Susceptible to Nonenzymatic Thiol Addition.Journal of the American Chemical Society · 2024Article
- Decarboxylation in Natural Products Biosynthesis.JACS Au · 2024Review
- CYP3A Mediates an Unusual C(spAngewandte Chemie (International ed. in English) · 2024Article
- Functional Model of Compound II of Cytochrome P450: Spectroscopic Characterization and Reactivity Studies of a FeJACS Au · 2024Article
- Biosynthesis and biotechnological production of the anti-obesity agent celastrol.Nature chemistry · 2023Article
- Dimer-assisted mechanism of (un)saturated fatty acid decarboxylation for alkene production.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Mechanistic analysis of carbon-carbon bond formation by deoxypodophyllotoxin synthase.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Halogen Transfer to Carbon Radicals by High-Valent Iron Chloride and Iron Fluoride Corroles.Inorganic chemistry · 2021Article
- Product Distributions of Cytochrome P450 OleTInternational journal of molecular sciences · 2021Article
- A Photoclick-Based High-Throughput Screening for the Directed Evolution of Decarboxylase OleT.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Production of Propene from n-Butanol: A Three-Step Cascade Utilizing the Cytochrome P450 Fatty Acid Decarboxylase OleTChembiochem : a European journal of chemical biology · 2020Article
- Bioengineering of Cytochrome P450 OleTMolecules (Basel, Switzerland) · 2020Article
- Alternative modes of OJournal of inorganic biochemistry · 2020Article
- Hydrogen Atom Abstraction by High-Valent Fe(OH) versus Mn(OH) Porphyrinoid Complexes: Mechanistic Insights from Experimental and Computational Studies.Inorganic chemistry · 2019Article
- Reduction Potentials of P450 Compounds I and II: Insight into the Thermodynamics of C-H Bond Activation.Journal of the American Chemical Society · 2019Article
- Mechanistic Studies of Fatty Acid Activation by CYP152 Peroxygenases Reveal Unexpected Desaturase Activity.ACS catalysis · 2019Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
OleT is a cytochrome P450 that catalyzes the hydrogen peroxide-dependent metabolism of Cn chain-length fatty acids to synthesize Cn-1 1-alkenes. The decarboxylation reaction provides a route for the production of drop-in hydrocarbon fuels from a renewable and abundant natural resource. This transformation is highly unusual for a P450, which typically uses an Fe(4+)-oxo intermediate known as compound I for the insertion of oxygen into organic substrates. OleT, previously shown to form compound I, catalyzes a different reaction. A large substrate kinetic isotope effect (≥8) for OleT compound I decay confirms that, like monooxygenation, alkene formation is initiated by substrate C-H bond abstraction. Rather than finalizing the reaction through rapid oxygen rebound, alkene synthesis proceeds through the formation of a reaction cycle intermediate with kinetics, optical properties, and reactivity indicative of an Fe(4+)-OH species, compound II. The direct observation of this intermediate, normally fleeting in hydroxylases, provides a rationale for the carbon-carbon scission reaction catalyzed by OleT.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.