LIQUID-CHROMATOGRAPHIC DETERMINATION OF CHIRAL EPOXIDES BY DERIVATIZATION WITH SODIUM SULFIDE, O-PHTHALALDEHYDE AND AN AMINO-ACID

A high-performance liquid chromatographic method for the enantiomeric determination of chiral epoxides is described. By derivatization with sodium sulphide, o-phthalaldehyde and an optically pure amino acid, chiral mono- and 2,2-disubstituted epoxides were converted into diastereomeric isoindole derivatives. Separation of the diastereomers was carried out by reversed-phase chromatography and the derivatives were detected fluorimetrically. For a series of nine monosubstituted epoxides, good enantioselectivity was obtained (alpha = 1.3-1.7). To study the effect on the chromatographic behaviour of the isoindole adducts, derivatization was carried out using four different amino acids. The derivatization procedure was optimized using glycidyl butyrate as test compound. Both the precision and accuracy of the method were investigated. The method was applied to monitor the enantiomeric purity of glycidyl butyrate obtained by lipase-catalysed hydrolysis of the racemate.