ArticleJournal of the American Chemical Society2011
Proton-coupled electron transfer reactions at a heme-propionate in an iron-protoporphyrin-IX model compound.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 63 citations in OpenAlex.
- Proton coupled electron transfer in myoglobin compound II auto-reduction revealed by temperature dependent rate behavior.Journal of inorganic biochemistry · 2026Article
- Unveiling an Ultrareduced State of Heme in Myoglobin.Journal of the American Chemical Society · 2025Article
- Flexibility and Hydration of the QJournal of chemical information and modeling · 2025Article
- Iridium Polypyridyl Carboxylates as Excited-State PCET Catalysts for the Functionalization of Unactivated C-H Bonds.Journal of the American Chemical Society · 2025Article
- Secondary Sphere Lewis Acid Activated Heme Superoxo Adducts Mimic Crucial Non-Covalent Interactions in IDO/TDO Heme Dioxygenases.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Electron transfer in biological systems.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2024Review
- Revealing the nature of covalently tethered distonic radical anions in the generation of heteroatom-centered radicals: evidence for the polarity-matching PCET pathway.Chemical science · 2024Article
- Enzyme-controlled stereoselective radical cyclization to arenes enabled by metalloredox biocatalysis.Nature catalysis · 2023Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Free Energies of Proton-Coupled Electron Transfer Reagents and Their Applications.Chemical reviews · 2022Review
- Photocatalytic Generation of Aminium Radical Cations for C─N Bond Formation.ACS catalysis · 2020Article
- Heme-FeJournal of the American Chemical Society · 2020Article
- A Heme Propionate Staples the Structure of CytochromeInorganic chemistry · 2019Article
- Rate-Driving Force Relationships in the Multisite Proton-Coupled Electron Transfer Activation of Ketones.Journal of the American Chemical Society · 2019Article
- Decarboxylation involving a ferryl, propionate, and a tyrosyl group in a radical relay yields hemeThe Journal of biological chemistry · 2018Article
- Histidine-Lysine Axial Ligand Switching in a Hemoglobin: A Role for Heme Propionates.Biochemistry · 2018Article
- Structure-Based Mechanism for Oxidative Decarboxylation Reactions Mediated by Amino Acids and Heme Propionates in Coproheme Decarboxylase (HemQ).Journal of the American Chemical Society · 2017Article
- Reactivity of the copper(iii)-hydroxide unit with phenols.Chemical science · 2017Article
- Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations.Angewandte Chemie (International ed. in English) · 2016Article
- Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities.Topics in current chemistry (Cham) · 2016Review
Corrections and comments
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
A heme model system has been developed in which the heme-propionate is the only proton donating/accepting site, using protoporphyrin IX-monomethyl esters (PPIX(MME)) and N-methylimidazole (MeIm). Proton-coupled electron transfer (PCET) reactions of these model compounds have been examined in acetonitrile solvent. (PPIX(MME))Fe(III)(MeIm)(2)-propionate (Fe(III)~CO(2)) is readily reduced by the ascorbate derivative 5,6-isopropylidine ascorbate to give (PPIX(MME))Fe(II)(MeIm)(2)-propionic acid (Fe(II)~CO(2)H). An excess of the hydroxylamine TEMPOH or of hydroquinone similarly reduces Fe(III)~CO(2), and TEMPO and benzoquinone oxidize Fe(II)~CO(2)H to return to Fe(III)~CO(2). The measured equilibrium constants, and the determined pK(a) and E(1/2) values, indicate that Fe(II)~CO(2)H has an effective bond dissociation free energy (BDFE) of 67.8 ± 0.6 kcal mol(-1). In these PPIX models, electron transfer occurs at the iron center and proton transfer occurs at the remote heme propionate. According to thermochemical and other arguments, the TEMPOH reaction occurs by concerted proton-electron transfer (CPET), and a similar pathway is indicated for the ascorbate derivative. Based on these results, heme propionates should be considered as potential key components of PCET/CPET active sites in heme proteins.
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