HPLC Separation of Diastereomeric Adducts of Glutatmione with Some K-Region Arene Oxides

Abstract

Abstract The diastereomeric glutathione (GSH) adducts of the K-region arene oxides phenanthrene 9,10-oxide, pyrene 4,5-oxide, (±)-benz[a]anthracene 5,6-oxide, and (±)-benzo[a]pyrene 4,5-oxide were separated by reversed phase liquid chromatography. Chromatographic conditions involved an organic base, Tris-base or diethylenetriamine (DETA), neutralized to pH 3 with phosphoric acid, and an alcohol, methanol or 1-propanol, as modifier. For (±)-benzo[a]pyrene 4,5-oxide, the use of DETA and 1-propanol provided a complete stereochemical profile of the thioether conjugates derived from this arene oxide. For the GSH adducts of (±)-benz[a]anthracene 5,6-oxide complete separation was achieved under two sets of chroraatographic conditions; methanol and 1-propanol enhanced the selectivity of the system for different sets of diastereomers. For both arene oxides, the GSH adducts with S-configuration eluted earlier than the R-diastereomers.