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Abstract: Uniformly sized molecularly imprinted polymers (MIPs) for Boc- L-Trp were prepared using ethylene glycol dimethacrylate (EDMA) as the cross-linker, and methacylic acid (MAA) and/or 4- vinylpyridine (4-VPY) as the functional monomers or without use of a functional monomer. The MIPs prepared were evaluated using acetonitrile or a mixture of phosphate buffer and acetonitrile as the mobile phase. The Boc-L-Trp-imprinted EDMA polymers can recognize Boc-L-Trp by its molecular shape, and can thus afford the enantioseparation of Boc-Trp. Besides the molecular shape recognition, the hydrophobic interactions with the polymer backbones as well as the hydrogen-bonding interactions of Boc- L-Trp with carboxyl and pyridyl groups in the polymers should work for the retention and recognition of Boc-L-Trp on the imprinted MAA-co-EDMA and 4-VPY-co-EDMA polymers, respectively, in the hydro-organic mobile phase. The hydrogen-bonding interactions seem to become dominant when only acetonitrile is used as the mobile phase. The Boc-L-Trp-imprinted 4-VPY-co-EDMA polymers gave the highest retentivity and enantioselectivity for Boc-Trp among the MIPs prepared. However, the simultaneous use of MAA and 4-VPY was not effective for the enantioseparation of Boc-Trp in a hydro-organic mobile phase. Furthermore, the baseline separation of Boc-Trp enantiomers was attained within 10 min on the Boc-L-Trp-imprinted 4-VPY-co-EDMA polymers under the optimized HPLC conditions