Geminal-dithiol-based precursors for reactive sulfur species.

Caged gem-dithiols have been developed as the donors of reactive sulfur species (RSS), but the chemistry of free gem-dithiols as RSS donors has not been well understood. Herein, we report the study of a free gem-dithiol, 1,3-diphenylpropane-2,2-dithiol, as the precursor for several RSS. It releases H2S under physiological conditions and can be converted to a mono-S-nitrosothiol, which serves as a NO donor. Furthermore, it can be converted to 3,3-dibenzyldithiirane, which is an active sulfur transfer reagent and can induce S-persulfidation.