Selenium Nucleophilicity and Electrophilicity in the Intra- and Intermolecular S_N2 Reactions of Selenenyl Sulfide Probes.

ABSTRACT: Chalcogenide exchange reactions are an important class of bimolecular nucleophilic substitution reactions (S_N2) involving sulfur and selenium species as nucleophile, central atom, and/or leaving group, which are fundamental throughout redox biology and metabolism. While thiol-disulfide exchange reactions have been deeply investigated, those involving selenium are less understood, especially with regards to the polarised selenenyl sulfides RSe-SR'. This functional group, which is fundamental in the biochemistry of glutathione peroxidase and thioredoxin reductase enzymes, was recently incorporated in the molecular scaffold of a TrxR1 specific probe, "RX1". Here, we investigate the S_N2@S and S_N2@Se reactions of selenenyl sulfides in silico to provide the first

SUBMITTER: Madabeni A 

PROVIDER: S-EPMC11855254 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature