Side chain functionality dominated the chromatography of N-protected amino acid on molecularly imprinted polymer

Molecularly imprinted polymer (MIP) with N-alpha-protected amino acid as the print molecule was prepared and used as the stationary phase for the chromatographic study of molecular recognition. Particles of MIP were prepared by photopolymerization of 4-vinylpyridine in the presence of tert-butyloxycarbonyl-L-tyrosine (BOC-L-Tyr) and packed into a column for the chromatographic resolution of Boc-L-Tyr and tert-butyloxycarbonyl-L-phenylalanine (BOC-L-Phe). These two N-alpha-protected amino acids that differ from each other in the side chain with one hydroxyl group on the benzene ring could be well separated on the MIP. A separation factor of about two was achieved by using a mixture of acetonitrile (99.5 v/v %) and acetic acid (0.5 v/v %) as the mobile phase. Results suggest that the interaction between hydroxyl group in the side chain of amino acid and pyridine in the polymer dominated the selective adsorption of print molecule on the MIP. (C) 2007 Wiley Periodicals, Inc.