Nucleophilicity of Glutathione: A Link to Michael Acceptor Reactivities

Mayer, Robert J. und Ofial, Armin R. (2019): Nucleophilicity of Glutathione: A Link to Michael Acceptor Reactivities. In: Angewandte Chemie-international Edition, Bd. 58, Nr. 49: S. 17704-17708

Abstract

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1433-7851
• Sprache: Englisch