ArticleProceedings of the National Academy of Sciences of the United States of America2016
Valence tautomerism in synthetic models of cytochrome P450.
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 9 papers.
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Who cites it
9 citing papers in PubMed, 38 citations in OpenAlex.
- Asynchronous Radical Addition-Coupled Two-Electron Transfer in P450-Catalyzed Arene Oxidation.ACS organic & inorganic Au · 2026Article
- Heme-NO Dilates Arteries via Mobilization of NO Moieties From an Intracellular NO Store Within Vascular Smooth Muscle Cells.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Unique Metal-Ligand Proton Tautomerism Underlying the Reversible Electrocatalytic NADJournal of the American Chemical Society · 2026Article
- De Novo design of α-helical heme binding proteins capable of versatile cofactor ligation.Methods in enzymology · 2025Article
- Selective Cobalt-Mediated Formation of Hydrogen Peroxide from Water under Mild Conditions via Ligand Redox Non-Innocence.Journal of the American Chemical Society · 2024Article
- Catalysis and Electron Transfer inChemical reviews · 2022Review
- The pH-Induced Selectivity Between Cysteine or Histidine Coordinated Heme in an Artificial α-Helical Metalloprotein.Angewandte Chemie (International ed. in English) · 2021Article
- Faraday cage screening reveals intrinsic aspects of the van der Waals attraction.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- van der Waals forces control ferroelectric-antiferroelectric ordering in CuInPChemical science · 2018Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
CytP450s have a cysteine-bound heme cofactor that, in its as-isolated resting (oxidized) form, can be conclusively described as a ferric thiolate species. Unlike the native enzyme, most synthetic thiolate-bound ferric porphyrins are unstable in air unless the axial thiolate ligand is sterically protected. Spectroscopic investigations on a series of synthetic mimics of cytP450 indicate that a thiolate-bound ferric porphyrin coexists in organic solutions at room temperature (RT) with a thiyl-radical bound ferrous porphyrin, i.e., its valence tautomer. The ferric thiolate state is favored by greater enthalpy and is air stable. The ferrous thiyl state is favored by entropy, populates at RT, and degrades in air. These ground states can be reversibly interchanged at RT by the addition or removal of water to the apolar medium. It is concluded that hydrogen bonding and local electrostatics protect the resting oxidized cytP450 active site from degradation in air by stabilizing the ferric thiolate ground state in contrast to its synthetic analogs.
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