Duchateau A, Crombach M, Aussems M, Bongers J
DSM Research, Geleen, The Netherlands.
J Chromatogr. 1989 Jan 6;461:419-28. doi: 10.1016/s0021-9673(00)94308-5.
A high-performance liquid chromatographic method for the enantiomeric analysis of a mixture of an alpha-amino acid and the corresponding acid amide is described. Reversed-phase chromatography with copper(II) acetate and N,N-di-n-propyl-L-alanine in the mobile phase are used for the separation. For Val and Val-NH2, several parameters affecting retention and enantioselectivity were investigated. The results indicate that by manipulation of pH, ionic strength, temperature, concentration of CuII, N,N-di-n-propyl-L-alanine and ion-pairing reagent, good control of enantiomeric separation can be achieved. For alpha-amino acid amides a mechanism is proposed which may account for the retention and enantioselectivity. Examples of enantiomeric analysis of mixtures of alpha-amino acids and alpha-amino acid amides with aliphatic, aromatic and polar side-chains are given. The method can be used for the control of the enantiomeric purity of alpha-amino acids and the corresponding acid amides obtained by enantioselective synthesis.
描述了一种用于对α-氨基酸与相应酰胺混合物进行对映体分析的高效液相色谱方法。采用反相色谱法，流动相中使用醋酸铜(II)和N,N-二正丙基-L-丙氨酸进行分离。对于缬氨酸（Val）和缬氨酰胺（Val-NH₂），研究了几个影响保留和对映选择性的参数。结果表明，通过调节pH值、离子强度、温度、CuII浓度、N,N-二正丙基-L-丙氨酸浓度和离子对试剂，可以很好地控制对映体分离。对于α-氨基酸酰胺，提出了一种可能解释保留和对映选择性的机制。给出了具有脂肪族、芳香族和极性侧链的α-氨基酸与α-氨基酸酰胺混合物对映体分析的示例。该方法可用于控制通过对映选择性合成获得的α-氨基酸和相应酰胺的对映体纯度。
