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Abstract: A new chiral stationary phase for nateglinide (N-(trans-4- isopropylcyclohexylcarbonyl)-D-phenylalanine) based on a molecularly imprinted polymer has been prepared by non-covalent imprinting. For chromatographic analysis the effects on the separation of mobile phase composition, flow rate, and temperature were investigated, and the optimum conditions for HPLC were shown to be: mobile phase, acetonitrile; flow rate, 0.5 mL min(-1); temperature, 25 degreesC. It was shown that the noteglinide-imprinted polymer was capable of recognizing the enantiomeric difference between nateglinide and its L enantiomer, whereas the non-imprinted polymer had no such ability. Scatchard analysis was used to investigate the binding characteristics of the noteglinide-imprinted stationary phase; this indicated that two classes of binding site were present in the imprinted polymer. The equilibrium dissociation constant (K-D) and the apparent maximum number (Q(max)) of high- and low-affinity binding sites were 3.7 x 10(-4) mol L-1 and 11.38 mumol g(-1), and 1.81 x 10(-3) mol L-1 and 27.73 mumol g(-1), respectively