ArticleNature chemistry2017
Characterization of a selenocysteine-ligated P450 compound I reveals direct link between electron donation and reactivity.
Article in Nature chemistry, 2017. 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.
- Discovery of noncanonical cytochrome P450 enzymes in nature.Nature chemical biology · 2026Article
- Review
- Regulation of ferryl reactivity by the cytochrome P450 decarboxylase OleT.Journal of inorganic biochemistry · 2025Article
- Planar asymmetric surface FeNature communications · 2025Article
- Modulation of heme peroxo nucleophilicities with axial ligands reveal key insights into the mechanistic landscape of nitric oxide synthase.Chemical science · 2025Article
- Non-Canonical Cytochrome P450 Enzymes in Nature.bioRxiv : the preprint server for biology · 2024Article
- Probing Ferryl Reactivity in a Nonheme Iron Oxygenase Using an Expanded Genetic Code.ACS catalysis · 2024Article
- Noncanonical Amino Acids in Biocatalysis.Chemical reviews · 2024Review
- Axial Ligation Impedes Proton-Coupled Electron-Transfer Reactivity of a Synthetic Compound-I Analogue.Journal of the American Chemical Society · 2024Article
- Enhanced Reactivities of Iron(IV)-Oxo Porphyrin Species in Oxidation Reactions Promoted by Intramolecular Hydrogen-Bonding.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Modulation of the Bonding between Copper and a Redox-Active Ligand by Hydrogen Bonds and Its Effect on Electronic Coupling and Spin States.Journal of the American Chemical Society · 2024Article
- Factors controlling the reactivity of synthetic compound-I Analogs.Journal of porphyrins and phthalocyanines · 2023Article
- The role of basicity in selective C-H bond activation by transition metal-oxidos.Dalton transactions (Cambridge, England : 2003) · 2023Review
- Photothermal-enabled single-atom catalysts for high-efficiency hydrogen peroxide photosynthesis from natural seawater.Nature communications · 2023Article
- Engineering enzyme activity using an expanded amino acid alphabet.Protein engineering, design & selection : PEDS · 2023Article
- Article
- Ferritin-Like Proteins: A Conserved Core for a Myriad of Enzyme Complexes.Sub-cellular biochemistry · 2022Article
- Direct Aerobic Generation of a Ferric Hydroperoxo Intermediate Via a Preorganized Secondary Coordination Sphere.Journal of the American Chemical Society · 2021Article
- A Noncanonical Tryptophan Analogue Reveals an Active Site Hydrogen Bond Controlling Ferryl Reactivity in a Heme Peroxidase.JACS Au · 2021Article
- Bound oxygen-atom transfer endows peroxidase-mimic M-N-C with high substrate selectivity.Chemical science · 2021Article
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Strong electron-donation from the axial thiolate ligand of cytochrome P450 has been proposed to increase the reactivity of compound I with respect to C-H bond activation. However, it has proven difficult to test this hypothesis, and a direct link between reactivity and electron donation has yet to be established. To make this connection, we have prepared a selenolate-ligated cytochrome P450 compound I intermediate. This isoelectronic perturbation allows for direct comparisons with the wild-type enzyme. Selenium incorporation was achieved using a cysteine auxotrophic Escherichia coli strain. The intermediate was prepared with meta-chloroperbenzoic acid and characterized by UV-visible, Mössbauer and electron paramagnetic resonance spectroscopies. Measurements revealed increased asymmetry around the ferryl moiety, consistent with increased electron donation from the axial selenolate ligand. In line with this observation, we find that the selenolate-ligated compound I cleaves C-H bonds more rapidly than the wild-type intermediate.
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