Chiral stationary phases (CSPs), CSP 1 and CSP 2, with a reverse stereochemical configuration, were prepared by covalently bonding (+)-and (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) to silica gel, respectively.These CSPs were used to resolve the enantiomers of several α-amino acids and primary amino compounds, affording reasonable and quite similar resolution behaviors.The elution orders of the α-amino acids shown were consistent, the (D)-enantiomers of all the analytes investigated in this study being selectively retained on CSP 1 derived from (+)-18-C-6-TA while the (L)-enantiomers being selectively retained on CSP 2 derived from (-)-18-C-6-TA, with the exception of serine, threonine and serine and threonine methyl esters.The reverse elution orders on the two CSPs with the antipode of the chiral selector were demonstrated to be very useful in the determination of the enantiomeric purity of optically enriched analytes.