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Abstract: A convenient "one step" preparation process of molecularly imprinted overoxidized-polypyrrole (oPPy) colloids by chemical polymerization and their high uptake ability and enantioselectivity are described. Since an oxidizing agent gives a different standard redox potential and rate of polymerization, the property of the resulting oPPy colloid can be controlled by the kind and concentration of the oxidizing agent. At higher concentrations of (NH4)(2)S2O8 (0.3 M), the overoxidation of PPy colloid automatically occurred. The extraction Of L-lactate as a dopant has created a shape- complementary cavity on the surface of the oPPy colloid through overoxidation following polymerization. The oPPy colloid exhibited an excellent selectivity not only on the alanine enantiomer but also on the difference in the side-chain size of amino acids. The uptake of oPPy colloid towards L-alanine over D-alanine was 11.3 mumol/g-colloid against 3.6 mumol/g. The molecularly imprinted cavity can also recognize the existences of the OH or CH3 substituents