Optical Resolution with Molecularly Imprinted Membranes Having Nanometer Sized Chiral Recognition Sites

本研究取得了以下结果：研究了L-谷氨酸-γ-苄酯和L-苯丙氨酸组成的八种三肽的手性识别能力。手性识别能力取决于三肽序列和氨基酸残基含量。含有较多谷氨酸衍生物残基或谷氨酸衍生物作为氨基末端残基的三肽衍生物显示出较高的分子识别能力，分子印迹四肽衍生物的手性识别能力，由L-天冬氨酸环己酯或L-谷氨酸γ-研究了环境极性对分子印迹四肽衍生物分子识别能力的影响也进行了调查。以50vol%乙醇水溶液为最佳组成，制备了寡肽分子印迹聚合物膜。结果表明，外消旋Ac-Trp混合物中的双酚A分子为D-异构体，其绝对构型与印迹分子完全相同，而寡肽钳分子为L-氨基酸残基，聚酰胺AMODEL印迹膜对双酚A的吸附选择性和选择透过性均高于对照膜。

The following results have been obtained through the present research project: The chiral recognition ability for eight types of tripeptides, consisiting of L-glutamic acid γ-benzyl ester and L-phenylalanine was studied. The chiral recognition ability depends on both the tripeptide sequence and the amino acid residue content. Tripeptide derivatives containing more glutamic acid derivative residue or glutamic acid derivative as an amino-terminal residue show higher molecular recognition ability.The chiral recognition ability of molecularly imprinted tetrapeptide derivatives, consisting of L-aspartic acid cyclohexyl ester or L-glutamic acid γ-benzyl ester was also studied.The effect of the polarity of the environment of the molecular recognition ability for molecularly imprinted tetrapeptide derivatives was also investigated. The optimum composition, with best chiral recognition, is a 50 vol% aqueous ethanol solution.Molecularly imprinted polymeric membranes were prepared from various oligopeptide tweezers. They recognized the D-isomer, of which absolute configuration was the same as that of the print molecule, from racemic Ac-Trp mixtures, while the oligopeptide tweezers consisted of L-amino acid residues.The imprinted membranes from polyamide AMODEL showed highe adsorption selectivity and permselectivity toward bisphenol A than the control membrane.