Nucleophilicity of Glutathione: A Link to Michael Acceptor Reactivities.

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 =s_N (N+E). We now determined the nucleophilic reactivity (N, s_N ) of glutathione (GSH) in aqueous solution at 20 °C to connect published GSH reactivities (k_GSH ) 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/s_N

SUBMITTER: Mayer RJ 

PROVIDER: S-EPMC6899611 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature