Resolution of the enantiomers of thiol compounds by reversed-phase liquid chromatography using chiral derivatization with 2,3,4,6-tetra-O-acetyl-β- d-glucopyranosyl isothiocyanate

Abstract

A new derivatization procedure has been developed for converting enantiomeric thiol compounds into their diastereomers for resolution by reversed-phase liquid chromatography. The thiol compounds were derivatized with 2,3,4,6-tetra-O-acetyl-β- d-glucopyranosyl isothiocyanate as chiral derivatization reagent and triethylamine as basic catalyst. The thiol group reacted smoothly with the isothiocyanate to form the dithiocarbamate derivative within 30 min at room temperature. The reaction mixture can be injected directly into the chromatograph without purification procedures. The ultraviolet detection wavelength was set at 250 nm, based on the absorption of the thiocarbonyl group. The resulting diastereomers were well separated on an octadecyl-bonded silica column with methanol-0.01 M phosphate buffer as the mobile phase.