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Abstract: Non-covalently molecularly imprinted polymers (MIPs) for beta(2)-amino acids were prepared for the first time. N-(2- chlorobenzyloxycarbonyl)-(R)-beta(2)-homophenylalanine (N-2- ClZ-(R)-beta(2)-HPhe)was imprinted with methacrylic acid (MAA) and/or 4-vinylpyridine (4-VPy) as the functional monomers, with ethylene glycol dimethacrylate ( EDMA) as the cross-linker. The MIPs made with different ratios of MAA:4-VPy were studied in HPLC mode. The results show that MIPs made with 4-VPy yielded the best chiral separation factor (alpha=1.86) for the template molecule. The importance for an efficient separation of pi- stacking interactions between the MIPs and the template molecule is demonstrated. Racemates of Z-alpha-amino acids and beta-amino acid analogues of the template were either not or poorly resolved by the MIPs, thus demonstrating the close three-dimensional complementarity of the MIPs' recognition sites with the template