Abstract: Molecule imprinting polymers (MIPs) with high chiral selectivity for N-alpha-protected amino acids were synthesized in polar solvent using acrylamide (AM) or combined functional monomer methacrylic acid (MAA) + vinyl pyridine (VP). Factors that influence the chiral selectivity of MIPs and mechanisms of the chiral recognition process were investigated. It was found that the rigid structure and the polar functional group of the print molecule were very important for the chiral selectivity of MIPs. For MIPs made using a combined functional monomer, ionic and hydrophobic interaction may be responsible for the chiral recognition process in aqeous media. The number of binding sites on MIPs and dissociation constants for the complex of enantiomers and MIPs were determined by frontal chromatography analysis. Copyright (C) 1999 John Wiley & Sons, Ltd