Isolation, characterization and thiol exchange reaction of penicillamine selenotrisulfides

Penicillamine selenotrisulfides formed by the reaction of selenite with D-, L-, and DL-penicillamines in the aqueous solution have been isolated and submitted to the spectroscopic and chromatographic analyses. FAB-MS spectra indicated the molecular ion peak (M+1)+ at m/z 377, which confirmed the molecular formula (C10H20N2O4S2Se) for all these selenotrisulfides. The [77Se]NMR and HPLC results showed that symmetric selenotrisulfides (DD and LL) were formed from D- and L-penicillamines, respectively, while asymmetric selenotrisulfide (DL) in addition to symmetric ones was formed from DL-penicillamine. The occurrence of thiol exchange reaction of selenotrisulfides was verified.