Separation of unmodified α-amino acid enantiomers by reverse phase HPLC

A novel chiral phase system is presented for the resolution of unmodified α-amino acid racemates which is composed of a reverse phase packing coated with N-alkyl-L-hydroxyproline (where alkyl is n-C7H15-, n-C10H21- and n-C16H33-) and a hydro-organic eluent containing copper(II)acetate. The factors controlling retention and enantioselectivity such as concentration of Cu(II)ion and pH of the eluent, addition of NH4Ac to the eluent, type and content of organic solvent of hydro-organic eluent and column temperature were examined. The extremely high enantioselectivity observed (α up to 16) is assumed to be caused by a three site sorbate-sorbent interaction involving bidentate coordination of two…