New chiral crown ether stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers

A new chiral stationary phase (CSP) for the liquid chromatographic separation of enantiomers was prepared by bonding a novel enantiopure (diphenyl-substituted 1,1'-binaphthyl) crown ether to 5 mum silica gel. The resulting CSP was applied to the separation of the enantiomers of various natural and unnatural alpha -amino acids. All alpha -amino acids tested were resolved very well on the new CSP, with the exception of proline, which does not contain a primary amino group. The resolution of alpha -amino acid enantiomers on this new CSP was found to be dependent on the type and amounts of organic and acidic modifiers, and on column temperature. (C) 2001 Elsevier Science B.V. All rights reserved.