Novel chiral polyureas were prepared from L-lysine-4-nitroanilide and 2,4-toluene diisocyanate. The polyurea thus prepared gave a durable self-standing membrane that can be directly converted into molecular recognition membranes by applying an alternative molecular imprinting. The Z-D-glutamic acid (D-Glu) molecularly imprinted membrane adsorbed D-Glu in preference to L-glutamic acid (L-Glu) from racemic mixture of Glu and vice versa. Those two types of molecularly imprinted membrane showed optical resolution ability, adopting a concentration gradient as a driving force for membrane transport. A facile method to predict permselectivity of racemic mixture of charged permeant was proposed. From the observed membrane resistance, the permselectivity was predicted. The predicted permselectivity coincided with the observed one. (C) 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 128: 123-131, 2013