Reversed-phase high-performance liquid chromatographic resolution of non-esterified enantiomeric amino acids by derivatization with 2,3,4,6-tetra-o-acetyl-β-d-glucopyranosyl isothiocyanate and 2,3,4-tri-o-acetyl-α-d-arabinopyranosyl isothiocyanate

Abstract

Novel methods for reversed-phase high-performance liquid chromatographic resolution of non-esterified amino acid enantiomers by the formation of diastereomers using two chiral reagents, 2,3,4,6-tetra-O-acetyl-βd-glucopyranosyl siothiocyanate and 2,3,4,-tri-O-acetyl-α-d-arabinopyranosyl isothiocyanate, are described. These compounds react readily with enantiomeric free amino acids at room temperature and the reaction mixture can be injected directly into the chromatograph. The separation of the enantiomers was monitored spectrophotometrically at 250 nm. Complete resolutions were observed for all enantiomers examined on a reversed-phase column eluted with methanol-10 mM potassium phosphate (pH 2.8). © 1981.