ArticleJournal of the American Chemical Society2022
Concerted and Stepwise Proton-Coupled Electron Transfer for Tryptophan-Derivative Oxidation with Water as the Primary Proton Acceptor: Clarifying a Controversy.
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 10 papers.
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10 citing papers in PubMed, 23 citations in OpenAlex.
- Mapping Proton-Coupled Electron Transfer With Real Space Coordinates.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Switching the proton-coupled electron transfer mechanism for non-canonical tyrosine residues in aChemical science · 2024Article
- Exploiting Cation Structure and Water Content in Modulating the Acidity of Ammonium Hydrogen Sulfate Protic Ionic Liquids.The journal of physical chemistry letters · 2024Article
- Modeling the Weak pH Dependence of Proton-Coupled Electron Transfer for Tryptophan Derivatives.The journal of physical chemistry letters · 2023Article
- Long-Range Conductivity in Proteins Mediated by Aromatic Residues.ACS physical chemistry Au · 2023Article
- Promoted Charge Separation and Long-Lived Charge-Separated State in Porphyrin-Viologen Dyad Nanoparticles.Journal of the American Chemical Society · 2023Article
- Aqueous Flavin Photoredox Catalysis Drives Exclusive C3-Alkylation of Indolyl Radical Cations in Route to Unnatural Tryptophan Mimetics.Organic letters · 2023Article
- Understanding the Key Roles of pH Buffer in Accelerating Lignin Degradation by Lignin Peroxidase.JACS Au · 2023Article
- Electrochemical and Structural Study of the Buried Tryptophan in Azurin: Effects of Hydration and Polarity on the Redox Potential of W48.The journal of physical chemistry. B · 2023Article
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4 authors at 1 institution in 1 country.
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Abstract
Concerted electron-proton transfer (CEPT) reactions avoid charged intermediates and may be energetically favorable for redox and radical-transfer reactions in natural and synthetic systems. Tryptophan (W) often partakes in radical-transfer chains in nature but has been proposed to only undergo sequential electron transfer followed by proton transfer when water is the primary proton acceptor. Nevertheless, our group has shown that oxidation of freely solvated tyrosine and W often exhibit weakly pH-dependent proton-coupled electron transfer (PCET) rate constants with moderate kinetic isotope effects (KIE ≈ 2-5), which could be associated with a CEPT mechanism. These results and conclusions have been questioned. Here, we present PCET rate constants for W derivatives with oxidized Ru- and Zn-porphyrin photosensitizers, extracted from laser flash-quench studies. Alternative quenching/photo-oxidation methods were used to avoid complications of previous studies, and both the amine and carboxylic acid groups of W were protected to make the indole the only deprotonable group. With a suitably tuned oxidant strength, we found an ET-limited reaction at pH < 4 and weakly pH-dependent rates at pH > ∼5 that are intrinsic to the PCET of the indole group with water (H
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