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

A new chiral stationary phase (CSP) for the liquid chromatographic separati on of enantiomers was prepared by bonding a novel enantiopure (diphenyl-sub stituted 1,1'-binaphthyl) crown ether to 5 mum silica gel. The resulting CS P was applied to the separation of the enantiomers of various natural and u nnatural alpha -amino acids. All alpha -amino acids tested were resolved ve ry well on the new CSP, with the exception of proline, which does not conta in a primary amino group. The resolution of alpha -amino acid enantiomers o n 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.