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Mayer, Robert J.; Ofial, Armin R. (2019): Nucleophilicity of Glutathione: A Link to Michael Acceptor Reactivities. In: Angewandte Chemie-international Edition, Vol. 58, No. 49: pp. 17704-17708
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Deprotonated glutathione is among the most potent biological nucleophiles and plays an important physiological role in cellular detoxification by forming covalent conjugates with Michael acceptors. The electrophilicity E of various Michael acceptors was characterized recently according to the Patz–Mayr relation lg k2=sN(N+E). We now determined the nucleophilic reactivity (N, sN) of glutathione (GSH) in aqueous solution at 20 °C to connect published GSH reactivities (kGSH) with Mayr's electrophilicity scale (E). In this way, electrophilicities E of more than 70 Michael acceptors could be estimated, which can now be used to systematically predict novel reactions with the multitude of nucleophiles whose nucleophilicity parameters N/sN are known.