Proton-coupled electron transfer: the mechanistic underpinning for radical transport and catalysis in biology
Open accessAbstract
Charge transport and catalysis in enzymes often rely on amino acid radicals as intermediates. The generation and transport of these radicals are synonymous with proton-coupled electron transfer (PCET), which intrinsically is a quantum mechanical effect as both the electron and proton tunnel. The caveat to PCET is that proton transfer (PT) is fundamentally limited to short distances relative to electron transfer (ET). This predicament is resolved in biology by the evolution of enzymes to control PT and ET coordinates on highly different length scales. In doing so, the enzyme imparts exquisite thermodynamic and kinetic controls over radical transport and radical-based catalysis at cofactor active sites. This discussion will present model systems containing orthogonal ET and PT pathways, thereby allowing the proton and electron tunnelling events to be disentangled. Against this mechanistic backdrop, PCET catalysis of oxygen–oxygen bond activation by mono-oxygenases is captured at biomimetic porphyrin redox platforms. The discussion concludes with the case study of radical-based quantum catalysis in a natural biological enzyme, class I Escherichia coli ribonucleotide reductase. Studies are presented that show the enzyme utilizes both collinear and orthogonal PCET to transport charge from an assembled diiron-tyrosyl radical cofactor to the active site over 35 Å away via an amino acid radical-hopping pathway spanning two protein subunits.
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Proton-coupled electron transfer mechanisms have been shown to underlie amino acid radical generation and transport.
“In biological energy storage, the importance of proton translocation driven by electron transfer was first noted in 1961 [89], and since then, proton-coupled electron transfer mechanisms [90] have been shown to underlie amino acid radical generation and transport [91] along with the activation of most substrate bonds at enzyme-active sites [92].”
From The future of quantum biology (2018) · cites this paper as [90]
Proton-coupled electron transfer mechanisms have been shown to underlie the activation of most substrate bonds at enzyme-active sites.
“In biological energy storage, the importance of proton translocation driven by electron transfer was first noted in 1961 [89], and since then, proton-coupled electron transfer mechanisms [90] have been shown to underlie amino acid radical generation and transport [91] along with the activation of most substrate bonds at enzyme-active sites [92].”
From The future of quantum biology (2018) · cites this paper as [90]
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Proton-Coupled Electron Transfer
Weinberg, D. R., Gagliardi, C. J., Hull, J. F., Murphy, C. F., Kent, C. A., Westlake, B. C., Paul, A., Ess, D. H., McCafferty, D. G., & Meyer, T. J. (2012) · Chemical Reviews · doi:10.1021/cr200177j · Cited by 2,433 · see citing works
Proton-coupled electron transfer
Huynh, M. H. V., & Meyer, T. J. (2007) · Chemical Reviews · doi:10.1021/cr0500030 · Cited by 1,659 · see citing works
Hydrogen Production by Molecular Photocatalysis
Esswein, A. J., & Nocera, D. G. (2007) · Chemical Reviews · doi:10.1021/cr050193e · Cited by 1,467 · see citing works
Self-citationMechanisms for DNA Charge Transport
Genereux, J. C., & Barton, J. K. (2010) · Chemical Reviews · doi:10.1021/cr900228f · Cited by 787 · see citing works
Synthetic Applications of Proton-Coupled Electron Transfer
Gentry, E. C., & Knowles, R. R. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00272 · Cited by 776 · see citing works
Cobalt–phosphate oxygen-evolving compound
Kanan, M. W., Surendranath, Y., & Nocera, D. G. (2008) · Chemical Society Reviews · doi:10.1039/b802885k · Cited by 740 · see citing works
Self-citationBiochemistry and Theory of Proton-Coupled Electron Transfer
Migliore, A., Polizzi, N. F., Therien, M. J., & Beratan, D. N. (2014) · Chemical Reviews · doi:10.1021/cr4006654 · Cited by 522 · see citing works
Reece, S. Y., & Nocera, D. G. (2009) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.78.080207.092132 · Cited by 484 · see citing works
“Enzymes often rely on the coupling of electrons and protons to affect primary metabolic steps involving charge transport and catalysis (1).”
BackgroundSelf-citationFree Energies of Proton-Coupled Electron Transfer Reagents and Their Applications
Agarwal, R. G., Coste, S. C., Groff, B. D., Heuer, A. M., Noh, H., Parada, G. A., Wise, C. F., Nichols, E. M., Warren, J. J., & Mayer, J. M. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00521 · Cited by 475 · see citing works
New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry
Liu, J., Lu, L., Wood, D., & Lin, S. (2020) · ACS Central Science · doi:10.1021/acscentsci.0c00549 · Cited by 470 · see citing works
Rono, L. J., Yayla, H. G., Wang, D. Y., Armstrong, M. F., & Knowles, R. R. (2013) · Journal of the American Chemical Society · doi:10.1021/ja4100595 · Cited by 467 · see citing works
Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis
Chang, L., An, Q., Duan, L., Feng, K., & Zuo, Z. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00256 · Cited by 458 · see citing works
Electronic Design Criteria for O−O Bond Formation via Metal−Oxo Complexes
Betley, T. A., Wu, Q., Voorhis, T. V., & Nocera, D. G. (2008) · Inorganic Chemistry · doi:10.1021/ic701972n · Cited by 425 · see citing works
Self-citationAn Unconventional Iron Nickel Catalyst for the Oxygen Evolution Reaction
Song, F., Busch, M. M., Lassalle‐Kaiser, B., Hsu, C., Petkucheva, E., Bensimon, M., Chen, H. M., Corminbœuf, C., & Hu, X. (2019) · ACS Central Science · doi:10.1021/acscentsci.9b00053 · Cited by 399 · see citing works
Chemistry of Personalized Solar Energy
Nocera, D. G. (2009) · Inorganic Chemistry · doi:10.1021/ic901328v · Cited by 395 · see citing works
Self-citationRole of Proton-Coupled Electron Transfer in O–O Bond Activation
Rosenthal, J., & Nocera, D. G. (2007) · Accounts of Chemical Research · doi:10.1021/ar7000638 · Cited by 392 · see citing works
Self-citationProton-Coupled Electron Flow in Protein Redox Machines
Dempsey, J. L., Winkler, J. R., & Gray, H. B. (2010) · Chemical Reviews · doi:10.1021/cr100182b · Cited by 300 · see citing works
Electrochemical Reduction of CO 2 at Functionalized Au Electrodes
Fang, Y., & Flake, J. C. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.6b11023 · Cited by 278 · see citing works
Marais, A., Adams, B., Ringsmuth, A. K., Ferretti, M., Gruber, J. M., Hendrikx, R., Schuld, M., Smith, S. L., Sinayskiy, I., Krüger, T. P. J., et al. (2018) · Journal of The Royal Society Interface · doi:10.1098/rsif.2018.0640 · Cited by 274 · see citing works
Reversible, Long-Range Radical Transfer in E. coli Class Ia Ribonucleotide Reductase
Minnihan, E. C., Nocera, D. G., & Stubbe, J. (2013) · Accounts of Chemical Research · doi:10.1021/ar4000407 · Cited by 269 · see citing works
Self-citationGentry, E. C., Rono, L. J., Hale, M. E., Matsuura, R., & Knowles, R. R. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.7b13616 · Cited by 262 · see citing works
Protein bioelectronics: a review of what we do and do not know
Bostick, C. D., Mukhopadhyay, S., Pecht, I., Sheves, M., Cahen, D., & Lederman, D. (2018) · Reports on Progress in Physics · doi:10.1088/1361-6633/aa85f2 · Cited by 254 · see citing works
“Proton-coupled electron transport (PCET) can also occur, which is especially prevalent at metal cofactors that activate carbon, oxygen, nitrogen, and sulphur atoms of enzyme substrate molecules [72].”
BackgroundKleinhaus, J. T., Wittkamp, F., Yadav, S., Siegmund, D., & Apfel, U. (2020) · Chemical Society Reviews · doi:10.1039/d0cs01089h · Cited by 253 · see citing works
Electronic Transport via Proteins
Amdursky, N., Marchak, D., Sepunaru, L., Pecht, I., Sheves, M., & Cahen, D. (2014) · Advanced Materials · doi:10.1002/adma.201402304 · Cited by 233 · see citing works
Catalytic generation of alkoxy radicals from unfunctionalized alcohols
Tsui, E., Wang, H., & Knowles, R. R. (2020) · Chemical Science · doi:10.1039/d0sc04542j · Cited by 233 · see citing works
Hangman Corroles: Efficient Synthesis and Oxygen Reaction Chemistry
Dogutan, D. K., Stoian, S. A., McGuire, R., Schwalbe, M., Teets, T. S., & Nocera, D. G. (2010) · Journal of the American Chemical Society · doi:10.1021/ja108904s · Cited by 219 · see citing works
Self-citationClass I Ribonucleotide Reductases: Metallocofactor Assembly and Repair In Vitro and In Vivo
Cotruvo, J. A., & Stubbe, J. (2011) · Annual Review of Biochemistry · doi:10.1146/annurev-biochem-061408-095817 · Cited by 212 · see citing works
“In the case of the class I RNRs, oxidation occurs by the Y• (class Ia, Ib) or MnIVFeIII cluster (class Ic) in the β2 subunit over a long distance, proposed to be 35 Å , via a specific proton-coupled electron transfer (PCET) pathway involving conserved aromatic residues (Figure 3) (40, 41).”
BackgroundSelf-citationProton-Coupled Electron Transfer of Tyrosine Oxidation: Buffer Dependence and Parallel Mechanisms
Irebo, T., Reece, S. Y., Sjödin, M., Nocera, D. G., & Hammarström, L. (2007) · Journal of the American Chemical Society · doi:10.1021/ja073012u · Cited by 211 · see citing works
Self-citationFairman, J. W., Wijerathna, S. R., Ahmad, M. F., Xu, H., Nakano, R., Jha, S., Prendergast, J., Welin, R. M., Flodin, S., Roos, A. K., et al. (2011) · Nature Structural & Molecular Biology · doi:10.1038/nsmb.2007 · Cited by 168 · see citing works
Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities
Miller, D. C., Tarantino, K. T., & Knowles, R. R. (2016) · Topics in Current Chemistry · doi:10.1007/s41061-016-0030-6 · Cited by 156 · see citing works
Machan, C. W., Chabolla, S. A., Yin, J., Gilson, M. K., Tezcan, F. A., & Kubiak, C. P. (2014) · Journal of the American Chemical Society · doi:10.1021/ja5085282 · Cited by 151 · see citing works
Tishchenko, O., Truhlar, D. G., Ceulemans, A. J., & Nguyen, M. T. (2008) · Journal of the American Chemical Society · doi:10.1021/ja7102907 · Cited by 147 · see citing works
Cotruvo, J. A., & Stubbe, J. (2012) · Metallomics · doi:10.1039/c2mt20142a · Cited by 143 · see citing works
Self-citationSeyedsayamdost, M. R., Xie, J., Chan, C. T. Y., Schultz, P. G., & Stubbe, J. (2007) · Journal of the American Chemical Society · doi:10.1021/ja076043y · Cited by 144 · see citing works
Self-citationDirect Observation of Hydrogen Tunneling Dynamics in Photoexcited Phenol
Roberts, G. M., Chatterley, A. S., Young, J. D., & Stavros, V. G. (2012) · The Journal of Physical Chemistry Letters · doi:10.1021/jz2016318 · Cited by 140 · see citing works
Elgrishi, N., McCarthy, B. D., Rountree, E. S., & Dempsey, J. L. (2016) · ACS Catalysis · doi:10.1021/acscatal.6b00778 · Cited by 139 · see citing works
Proton‐Coupled Electron Transfer in Photoredox Catalytic Reactions
Hoffmann, N. (2017) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201601445 · Cited by 123 · see citing works
Nguyen, L. Q., & Knowles, R. R. (2016) · ACS Catalysis · doi:10.1021/acscatal.6b00486 · Cited by 120 · see citing works
Low-barrier hydrogen bonds in enzyme cooperativity
Dai, S., Funk, L.-M., von Pappenheim, F. R., Sautner, V., Paulikat, M., Schröder, B., Uranga, J., Mata, R. A., & Tittmann, K. (2019) · Nature · doi:10.1038/s41586-019-1581-9 · Cited by 117 · see citing works
Excited-State Quenching by Proton-Coupled Electron Transfer
Concepcion, J. J., Brennaman, M. K., Deyton, J. R., Lebedeva, N. V., Forbes, M. D. E., Papanikolas, J. M., & Meyer, T. J. (2007) · Journal of the American Chemical Society · doi:10.1021/ja069049g · Cited by 116 · see citing works
Efficient photochemical electron transfer sensitization of homogeneous organic reactions
Hoffmann, N. (2008) · Journal of Photochemistry and Photobiology C Photochemistry Reviews · doi:10.1016/j.jphotochemrev.2008.04.002 · Cited by 112 · see citing works
Munir, A., Joya, K. S., Haq, T. U., Babar, N., Hussain, S. Z., Qurashi, A., Ullah, N., & Hussaın, I. (2018) · ChemSusChem · doi:10.1002/cssc.201802069 · Cited by 111 · see citing works
Lukács, A., Eker, A. P. M., Byrdin, M., Brettel, K., & Vos, M. H. (2008) · Journal of the American Chemical Society · doi:10.1021/ja805261m · Cited by 109 · see citing works
Stoner‐Ma, D., Jaye, A. A., Ronayne, K. L., Nappa, J., Meech, S. R., & Tonge, P. J. (2008) · Journal of the American Chemical Society · doi:10.1021/ja0754507 · Cited by 109 · see citing works
Structural interconversions modulate activity of Escherichia coli ribonucleotide reductase
Ando, N., Brignole, E. J., Zimanyi, C. M., Funk, M. A., Yokoyama, K., Asturias, F. J., Stubbe, J., & Drennan, C. L. (2011) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1112715108 · Cited by 107 · see citing works
“For each turnover, α2, β2, substrate and effector must interact, triggering long-range proton-coupled electron transfer (PCET) reducing Y122• in β2 and oxidizing C439 to a thiyl radical in the active site of α2, over an unprecedented distance of >35 Å (13, 15, 16) (Fig.”
BackgroundSelf-citationPopp, B. V., & Stahl, S. S. (2009) · Chemistry - A European Journal · doi:10.1002/chem.200802311 · Cited by 105 · see citing works
Morris, W. D., & Mayer, J. M. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b03562 · Cited by 96 · see citing works
Trends in Ground-State Entropies for Transition Metal Based Hydrogen Atom Transfer Reactions
Mader, E. A., Manner, V. W., Markle, T. F., Wu, A., Franz, J. A., & Mayer, J. M. (2009) · Journal of the American Chemical Society · doi:10.1021/ja8081846 · Cited by 95 · see citing works
Proton-Directed Redox Control of O−O Bond Activation by Heme Hydroperoxidase Models
Soper, J. D., Kryatov, S. V., Rybak-Akimova, E. V., & Nocera, D. G. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0683032 · Cited by 94 · see citing works
Self-citationDirect simulation of proton-coupled electron transfer across multiple regimes
Kretchmer, J. S., & Miller, T. F. (2013) · The Journal of Chemical Physics · doi:10.1063/1.4797462 · Cited by 91 · see citing works
Yokoyama, K., Uhlin, U., & Stubbe, J. (2010) · Journal of the American Chemical Society · doi:10.1021/ja101097p · Cited by 85 · see citing works
Self-citationIdentification of a Cyclic Nucleotide as a Cryptic Intermediate in Molybdenum Cofactor Biosynthesis
Hover, B. M., Loksztejn, A., Ribeiro, A. A., & Yokoyama, K. (2013) · Journal of the American Chemical Society · doi:10.1021/ja401781t · Cited by 85 · see citing works
Betley, T. A., Surendranath, Y., Childress, M. V., Alliger, G. E., Fu, R., Cummins, C. C., & Nocera, D. G. (2007) · Philosophical Transactions of the Royal Society B Biological Sciences · doi:10.1098/rstb.2007.2226 · Cited by 83 · see citing works
“The importance of the PCET mechanism in the activation of water and other small molecules has been presented in a recent Philosophical Society Discussion (Reece et al. 2006).”
BackgroundSelf-citationElectron-Driven Acid-Base Chemistry: Proton Transfer from Hydrogen Chloride to Ammonia
Eustis, S. N., Radisic, D., Bowen, K. H., Bachorz, R. A., Harańczyk, M., Schenter, G. K., & Gutowski, M. S. (2008) · Science · doi:10.1126/science.1151614 · Cited by 83 · see citing works
Photoinduced Electron Transfer and Hole Migration in Nanosized Helical Aromatic Oligoamide Foldamers
Li, X., Markandeya, N., Jonušauskas, G., McClenaghan, N. D., Maurizot, V., Denisov, S. A., & Huc, I. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b05668 · Cited by 83 · see citing works
Hydrogen bond dynamics in the active site of photoactive yellow protein
Sigala, P. A., Tsuchida, M. A., & Herschlag, D. (2009) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0900168106 · Cited by 82 · see citing works
“Hydrogen bond coupling may be particularly crucial for modulating the proximity of donor and acceptor groups within proteins catalyzing proton-coupled electron transfer, due to the exquisite sensitivity of electron transfer efficiency to the donor-acceptor distance (5, 6, 46).”
BackgroundWenger, O. S. (2014) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2014.03.025 · Cited by 80 · see citing works
Proton coupled electron transfer and redox active tyrosines in Photosystem II
Barry, B. A. (2011) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2011.01.026 · Cited by 79 · see citing works
“However, when the distance is long, separate or orthogonal electron and proton acceptors may be used [11].”
BackgroundThe self-organizing fractal theory as a universal discovery method: the phenomenon of life
Kurakin, A. V. (2011) · Theoretical Biology and Medical Modelling · doi:10.1186/1742-4682-8-4 · Cited by 80 · see citing works
“Thus, electron transport to and from active sites can occur in concert with protons hopping “orthogonally” to and from active sites along amino acid chains or structured water channels [30,71,74,75].”
BackgroundInfluentialPromoting proton coupled electron transfer in redox catalysts through molecular design
Thammavongsy, Z., Mercer, I. P., & Yang, J. Y. (2019) · Chemical Communications · doi:10.1039/c9cc05139b · Cited by 75 · see citing works
MacLean, P. D., Chapman, E. E., Dobrowolski, S. L., Thompson, A., & Barclay, L. R. C. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo8005073 · Cited by 74 · see citing works
Saitô, T., Yamanaka, S., Kanda, K., Isobe, H., Takano, Y., Shigeta, Y., Umena, Y., Kawakami, K., Shen, J., Kamiya, N., et al. (2011) · International Journal of Quantum Chemistry · doi:10.1002/qua.23218 · Cited by 72 · see citing works
Catalase and Epoxidation Activity of Manganese Salen Complexes Bearing Two Xanthene Scaffolds
Yang, J. Y., & Nocera, D. G. (2007) · Journal of the American Chemical Society · doi:10.1021/ja070358w · Cited by 71 · see citing works
Self-citationSong, N., Gagliardi, C. J., Binstead, R. A., Zhang, M., Thorp, H. H., & Meyer, T. J. (2012) · Journal of the American Chemical Society · doi:10.1021/ja308700t · Cited by 68 · see citing works
Wörsdörfer, B., Conner, D. A., Yokoyama, K., Livada, J., Seyedsayamdost, M. R., Jiang, W., Silakov, A., Stubbe, J., Bollinger, J. M., Jr., & Krebs, C. (2013) · Journal of the American Chemical Society · doi:10.1021/ja401342s · Cited by 68 · see citing works
Self-citationYokoyama, K., Smith, A. A., Corzilius, B., Griffin, R. G., & Stubbe, J. (2011) · Journal of the American Chemical Society · doi:10.1021/ja207455k · Cited by 67 · see citing works
Self-citationYang, W.-Y., Breiner, B., Kovalenko, S. V., Ben, C., Singh, M. P., LeGrand, S. N., Sang, Q. A., Strouse, G. F., Copland, J. A., & Alabugin, I. V. (2009) · Journal of the American Chemical Society · doi:10.1021/ja902140m · Cited by 66 · see citing works
Reversible voltammograms and a Pourbaix diagram for a protein tyrosine radical
Berry, B. W., Martínez-Rivera, M. C., & Tommos, C. (2012) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1112057109 · Cited by 66 · see citing works
Concerted Proton-Electron Transfers: Fundamentals and Recent Developments
Savéant, J. (2014) · Annual Review of Analytical Chemistry · doi:10.1146/annurev-anchem-071213-020315 · Cited by 66 · see citing works
Celis, A. I., Gauss, G. H., Streit, B. R., Shisler, K. A., Moraski, G. C., Rodgers, K. R., Lukat-Rodgers, G. S., Peters, J. W., & DuBois, J. L. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b11324 · Cited by 64 · see citing works
Oliver, T. A. A., Zhang, Y., Roy, A., Ashfold, M. N. R., & Bradforth, S. E. (2015) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.5b01861 · Cited by 63 · see citing works
“14,15 To date, electronic structure calculations have only examined small phenol–water clusters, revealing that direct photoexcitation to the 1 πσ * state leads to a net transfer of an H atom to the water cluster.”
BackgroundA Hot Oxidant, 3-NO2Y122 Radical, Unmasks Conformational Gating in Ribonucleotide Reductase
Yokoyama, K., Uhlin, U., & Stubbe, J. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1069344 · Cited by 63 · see citing works
Self-citationFrom Enzymes to Functional Materials—Towards Activation of Small Molecules
Möller, F., Piontek, S., Miller, R. G., & Apfel, U. (2017) · Chemistry - A European Journal · doi:10.1002/chem.201703451 · Cited by 62 · see citing works
Martínez, A., Peluffo, G., Petruk, A. A., Hugo, M., Piñeyro, M. D., Demicheli, V., Moreno, D. M., Lima, A. E., Batthyány, C., Durán, R., et al. (2014) · Journal of Biological Chemistry · doi:10.1074/jbc.m113.545590 · Cited by 60 · see citing works
“The structural data are thus consistent with the existence of an IET mechanism in FeSODB involving Cys, Trp and the active site tyrosine residue, as observed previously for other proteins (33, 79, 80).”
MethodBollinger, J. M., Jr., Jiang, W., Green, M. T., & Krebs, C. (2008) · Current Opinion in Structural Biology · doi:10.1016/j.sbi.2008.11.007 · Cited by 60 · see citing works
Demonstration of Proton-coupled Electron Transfer in the Copper-containing Nitrite Reductases
Brenner, S., Heyes, D. J., Hay, S., Hough, M. A., Eady, R. R., Hasnain, S. S., & Scrutton, N. S. (2009) · Journal of Biological Chemistry · doi:10.1074/jbc.m109.012245 · Cited by 57 · see citing works
Jia, J., Ho, Y. A., Bülow, R. F., & Rueping, M. (2018) · Chemistry - A European Journal · doi:10.1002/chem.201802907 · Cited by 55 · see citing works
Reece, S. Y., Seyedsayamdost, M. R., Stubbe, J., & Nocera, D. G. (2007) · Journal of the American Chemical Society · doi:10.1021/ja074452o · Cited by 55 · see citing works
Self-citationElectron Transfer Reactions of Fluorotyrosyl Radicals
Reece, S. Y., Seyedsayamdost, M. R., Stubbe, J., & Nocera, D. G. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0636688 · Cited by 55 · see citing works
Self-citationKunos, C. A., Chu, E., Beumer, J. H., Sznol, M., & Ivy, S. P. (2016) · Cancer Chemotherapy and Pharmacology · doi:10.1007/s00280-016-3200-x · Cited by 54 · see citing works
“RNR generates de novo dNDPs by proton-coupled electron transfer from two tyrosyl radical sites (M2 or M2b [p53R2] subunits) to active sites (M1 subunits) [7, 8].”
Yang, J. L., Nocera, D. G., & Pizano, A. A. (2012) · DSpace@MIT (Massachusetts Institute of Technology) · Cited by 53 · see citing works
Self-citationXanthene-Modified and Hangman Iron Corroles
Schwalbe, M., Dogutan, D. K., Stoian, S. A., Teets, T. S., & Nocera, D. G. (2011) · Inorganic Chemistry · doi:10.1021/ic101943h · Cited by 53 · see citing works
Self-citationArgirević, T., Riplinger, C., Stubbe, J., Neese, F., & Bennati, M. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3071682 · Cited by 53 · see citing works
Self-citationPhoto-ribonucleotide reductase β2 by selective cysteine labeling with a radical phototrigger
Pizano, A. A., Lutterman, D. A., Holder, P. G., Teets, T. S., Stubbe, J., & Nocera, D. G. (2011) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1115778108 · Cited by 53 · see citing works
“Accordingly, the importance of radicals in biological function (5) provides an imperative for the description of PCET in natural systems whose functions derive from radical-based chemistry (6).”
BackgroundSelf-citationNayak, M. K. (2012) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/j.jphotochem.2012.05.018 · Cited by 53 · see citing works
Inhibitors of the Cancer Target Ribonucleotide Reductase, Past and Present
Huff, S. E., Winter, J. M., & Dealwis, C. G. (2022) · Biomolecules · doi:10.3390/biom12060815 · Cited by 52 · see citing works
Tryptophan-Accelerated Electron Flow Across a Protein–Protein Interface
Takematsu, K., Williamson, H. R., Blanco‐Rodríguez, A. M., Sokolová, L., Nikolovski, P., Kaiser, J. T., Towrie, M., Clark, I. P., Vlček, A., Winkler, J. R., et al. (2013) · Journal of the American Chemical Society · doi:10.1021/ja406830d · Cited by 51 · see citing works
Conformationally Dynamic Radical Transfer within Ribonucleotide Reductase
Greene, B. L., Taguchi, A. T., Stubbe, J., & Nocera, D. G. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b08192 · Cited by 51 · see citing works
Self-citationProton transfer reactions: From photochemistry to biochemistry and bioenergetics
Demchenko, A. P. (2023) · BBA Advances · doi:10.1016/j.bbadva.2023.100085 · Cited by 50 · see citing works
“4 because these reactions are extremely fast and they do not allow catching and characterizing the intermediates [11,44].”
BackgroundInvestigation of in Vivo Diferric Tyrosyl Radical Formation in Saccharomyces cerevisiae Rnr2 Protein
Zhang, Y., Liu, L., Wu, X., An, X., Stubbe, J., & Huang, M. (2011) · Journal of Biological Chemistry · doi:10.1074/jbc.m111.294074 · Cited by 50 · see citing works
Self-citationMinnihan, E. C., Ando, N., Brignole, E. J., Olshansky, L., Chittuluru, J. R., Asturias, F. J., Drennan, C. L., Nocera, D. G., & Stubbe, J. (2013) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1220691110 · Cited by 50 · see citing works
“1A has emerged from experiments conducted in our laboratories (12, 13).”
MethodSelf-citationKasanmascheff, M., Lee, W., Nick, T. U., Stubbe, J., & Bennati, M. (2015) · Chemical Science · doi:10.1039/c5sc03460d · Cited by 50 · see citing works
Self-citationShafaat, H. S., Leigh, B. S., Tauber, M. J., & Kim, J. E. (2010) · Journal of the American Chemical Society · doi:10.1021/ja101322g · Cited by 50 · see citing works
Biological wires, communication systems, and implications for disease
Friesen, D. E., Craddock, T. J. A., Kalra, A. P., & Tuszynski, J. A. (2015) · Biosystems · doi:10.1016/j.biosystems.2014.10.006 · Cited by 48 · see citing works
“has been studied (Blumenfeld and Chernavskii, 1973; Reece et al., 2006).”
Efficient Synthesis of Hangman Porphyrins
Dogutan, D. K., Bediako, D. K., Teets, T. S., Schwalbe, M., & Nocera, D. G. (2010) · Organic Letters · doi:10.1021/ol902947h · Cited by 49 · see citing works
Self-citationReece, S. Y., Seyedsayamdost, M. R., Stubbe, J., & Nocera, D. G. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0704434 · Cited by 49 · see citing works
Self-citationBarry, B. A., Chen, J., Keough, J. M., Jenson, D. L., Offenbacher, A. R., & Pagba, C. V. (2012) · The Journal of Physical Chemistry Letters · doi:10.1021/jz2014117 · Cited by 48 · see citing works
Yokoyama, K., Ohmori, D., Kudo, F., & Eguchi, T. (2008) · Biochemistry · doi:10.1021/bi800509x · Cited by 48 · see citing works
Triapine Radiochemotherapy in Advanced Stage Cervical Cancer
Kunos, C. A., & Ivy, S. P. (2018) · Frontiers in Oncology · doi:10.3389/fonc.2018.00149 · Cited by 47 · see citing works
Högbom, M. (2011) · Metallomics · doi:10.1039/c0mt00095g · Cited by 46 · see citing works
- Authors
- Reece, S. Y., Hodgkiss, J. M., Stubbe, J., & Nocera, D. G.
- Affiliations
- Massachusetts Institute of Technology (US)
- Venue
- Philosophical Transactions of the Royal Society B: Biological Sciences
- Publisher
- The Royal Society
- Published
- 2006-07-17
- Volume
- 361
- Issue
- 1472
- Pages
- 1351-1364
- ISSN
- 0962-8436 (ISSN-L)
- 1471-2970
- PMC
- PMC1647304
- OpenAlex
- W2161929344
- Cited by
- 294
- References
- 106
- Citations by year
- 2026: 9 · 2025: 6 · 2024: 9 · 2023: 4 · 2022: 7 · 2021: 13 · 2020: 12 · 2019: 12 · 2018: 15 · 2017: 10 · 2016: 14 · 2015: 14 · 2014: 17 · 2013: 15 · 2012: 27
- FWCI
- 14.60
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Philosophical Transactions of the Royal Society B Biological Sciences (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institute of General Medical Sciences (GM29595, GM47274, R01GM047274, R01GM029595)
- Topics
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Physical Sciences › Energy › Renewable Energy, Sustainability and the Environment › Metalloenzymes and iron-sulfur proteins
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- proton-coupled electron transfer, amino acid radicals, radical transport, proton tunneling, electron tunneling, enzyme catalysis, mixed function oxidase, quantum catalysis, ribonucleotide reductase
- MeSH terms
- Amino Acids, Catalysis, Electron Transport, Enzymes, Escherichia coli, Free Radicals, Kinetics, Models, Chemical, Models, Molecular, Oxygen, Protons, Ribonucleotide Reductases, Thermodynamics, Signal Transduction
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