Shim Yong-Ho, Yilmaz Ecevit, Lavielle Solange, Haupt Karsten
Université P. et M. Curie--Paris VI, UMR 7613 CNRS, Paris, France.
Analyst. 2004 Dec;129(12):1211-5. doi: 10.1039/b409836f. Epub 2004 Oct 13.
Non-covalently molecularly imprinted polymers (MIPs) for beta2-amino acids were prepared for the first time. N-(2-chlorobenzyloxycarbonyl)-(R)-beta2-homophenylalanine (N-2-ClZ-(R)-beta2-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.
首次制备了用于β2-氨基酸的非共价分子印迹聚合物（MIP）。以N-(2-氯苄氧基羰基)-(R)-β2-高苯丙氨酸（N-2-ClZ-(R)-β2-HPhe）为模板，以甲基丙烯酸（MAA）和/或4-乙烯基吡啶（4-VPy）为功能单体，乙二醇二甲基丙烯酸酯（EDMA）为交联剂进行印迹。研究了不同MAA:4-VPy比例制备的MIP在高效液相色谱模式下的情况。结果表明，用4-VPy制备的MIP对模板分子产生了最佳的手性分离因子（α = 1.86）。证明了MIP与模板分子之间π-堆积相互作用对有效分离的重要性。Z-α-氨基酸的外消旋体和模板的β-氨基酸类似物要么不能被MIP分离，要么分离效果很差，从而证明了MIP识别位点与模板之间紧密的三维互补性。
