The HPLC enantioresolution of phenyl lsothiocyanated amino acids on vancomycin bonded phase using the acetonitrile-based mobile phase: A comparison to the teicoplanin phase

摘要

The phenyl isothiocyanate, an electrophilic reagent for peptide chain sequencing, is used to pre-column derivatize a variety of alpha-amino acids in alkaline medium before their enantioresolution on a vancomycin bonded chiral phase using the acetonitrile-based mobile phase. The observed resolution is believed to be due to the re-location of the hydrogen receptor site from sulfur to nitrogen on the isothiocyanyl fragment of derivatizing reagent, which in turn changes the enantioselectivity. Under the same chromatographic conditions, the resolution for N-benzoylated, 3,5-dinitrobenzoylated and N-carbobenzyloxylated amino acids is either not found or unsatisfactory. Also, no resolution is obtained in the reversed- or normal phase mode for all phenyl isothiocyanated amino acids examined in this study. [References: 18]