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Amino acid resolution using supported liquid membranes

机译:使用支持的液膜解析氨基酸

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Separation of chiral intermediates is of tremendous importance in a number of fields.In the pharmaceutical industry,it is often essential to determine the pharmacological and toxicological activity of each stereoisomer in drugs that consist of more than one stereoisomer.As new single stereoisomer drugs are developed the need for new chiral separation methods will increase.The resolution of phenylalanine and methionine has been studied using a supported liquid membrane.Experiments were conducted in batch mode using a diffusion cell.The organic liquid membrane phase consisted of a 50%:50% (volume basis) decane:decanol solvent.Resolution of the racemic amino acid feed solution depended upon the formation of a chiral transition metal complex with each of the enantiomers of the amino acid to be resolved.The chiral carrier and transition metal were N-decyl-(L)-hydroxyproline and copper(II).The ratio of copper to N-decyl-(L)-hydroxyproline was 1:2.Resolution of the two amino acid enantiomers depends upon the solubility and stability of the resulting diastereomeric transition metal complex.The results obtained here indicate that the experimentally determined separation factor and flux of each enantiomer initially decrease rapidly.The initial separation factor is the highest separation factor achieved during the run.The highest separation factors for phenylalanine and methionine were 1.8 and 1.9,respectively.The initial separation factor may be used to determine the ratio of the enantioselective equilibrium constants for the D and L stereoisomers.As the two enantiomers are resolved,the ratio of the D to L enantiomer in the feed suspension will deviate from one.The ratio of the enantioselective equilibrium constants may be used to estimate the maximum concentration difference possible between the D and L enantiomers in the feed solution.
机译:在许多领域中,手性中间体的分离具有极其重要的意义。在制药工业中,确定一种或多种立体异构体的药物中每种立体异构体的药理和毒理活性通常至关重要。随着新的单一立体异构体药物的开发对新的手性分离方法的需求将增加。使用支撑液膜研究了苯丙氨酸和蛋氨酸的分离度。使用扩散池以分批方式进行了实验。有机液膜相占50%:50%(外消旋氨基酸进料溶液的溶解度取决于要拆分的氨基酸的每种对映异构体的手性过渡金属络合物的形成,手性载体和过渡金属是N-癸基- (L)-羟基脯氨酸和铜(II)。铜与N-癸基-(L)-羟基脯氨酸的比例为1:2。两种氨基酸对映体的拆分取决于所得非对映异构过渡金属配合物的溶解度和稳定性。此处获得的结果表明,实验确定的每种对映异构体的分离因子和通量最初迅速下降,初始分离因子是运行中获得的最高分离因子。苯丙氨酸和蛋氨酸的分离系数分别为1.8和1.9。初始分离系数可用于确定D和L立体异构体的对映选择性平衡常数的比率。当两个对映异构体拆分后,D与L的比率进料悬浮液中的对映异构体将偏离一个。对映选择性平衡常数的比率可用于估算进料溶液中D和L对映异构体之间可能存在的最大浓度差。

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