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首页> 外文期刊>American Journal of Analytical Chemistry >Chiral Recognition of Binaphthyl Derivatives with L-Undecyl Leucine Surfactants in the Presence of Sodium and Lysine Counterions
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Chiral Recognition of Binaphthyl Derivatives with L-Undecyl Leucine Surfactants in the Presence of Sodium and Lysine Counterions

机译：在钠和赖氨酸抗衡膜存在下对L-未甲甲基亮氨酸表面活性剂的手性识别苯并基衍生物

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摘要

This study investigates the effect of counterions on the chiral recognition of 1,1'-Binaphthyl-2,2'-diamine (BNA) and 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate (BNP) enantiomers when using an amino acid-based surfactant undecanoyl L-leucine (und-Leu) as the chiral pseudostationary phase in capillary electrophoresis. The effects of using two different counterions (sodium and lysine) on the chiral recognition of binaphthyl derivatives were compared at varying pH conditions. The enantiomeric separation of BNA and BNP enantiomers via capillary electrophoresis, using und-Leu as the chiral recognition medium, significantly improved the enantiomeric resolution in capillary electrophoresis at pH 7 when using Lysine counterions as compared to using sodium as the counterion. More specifically, at a surfactant concentration of 45 mM, at pH 7, a significant increase in chiral selectivity was observed when lysine was used as the counterion compared to sodium. The enantiomeric resolution of BNA and BNP increased by 6-fold and 1.1-fold, respectively, in capillary electrophoresis experiments when lysine was utilized as the counterion compared to using sodium. Furthermore, the retention factor of BNA and BNP enantiomers also increased approximately 3.5-fold and 4-fold, respectively, in the presence of lysine counterions as compared to using sodium counterions. When running buffer in capillary electrophoresis was increased to pH 11, the resolution and retention factors were nearly identical when comparing the effects of the sodium and lysine counterions. This signifies the important role of lysine’s positive net charge on chiral recognition. This study provides insight into the potential advantages of using cationic, pH-dependent counterions such as lysine to significantly improve the chiral recognition of binaphthyl derivatives when using chiral anionic surfactants as the pseudostationary phase in capillary electrophoresis.
机译：本研究调查抗衡离子对1,1'-二萘基-2,2'-二胺（BNA）和1,1'-二苯甲基-2,2'-二氢磷酸酯（BNP）对磷酸酯的影响的影响基于氨基酸的表面活性剂Undecanoyl L-亮氨酸（und-Leu）作为毛细管电泳中的手性假期相。在不同的pH条件下比较使用两种不同抗衡离子（钠和赖氨酸）对二吡啶基衍生物的手性识别的影响。通过荧光液作为手性识别介质，通过毛细管电泳的BNA和BNP对映异构体的对映体分离，当使用赖氨酸作为抗衡离子相比，使用赖氨酸抗体时，在pH7时显着改善了pH7的毛细血管电泳中的对映体分辨率。更具体地，在pH7处的表面活性剂浓度为45mm，当与钠相比，当使用赖氨酸时，观察到赖氨酸的手性选择性显着增加。当与使用钠相比，当使用赖氨酸时，BNA和BNP的对映体分辨率分别在毛细管电泳实验中增加了6倍和1.1倍。此外，与使用钠抗体相比，BNA和BNP对映体的保留因子分别在赖氨酸抗衡膜存在下分别增加约3.5倍和4倍。在毛细管电泳中的运行缓冲液增加到pH11时，在比较钠和赖氨酸抗衡局的影响时，分辨率和保留因子几乎相同。这意味着Lysine积极净电荷对手性承认的重要作用。本研究提供了对使用阳离子，pH依赖性抗衡离子（例如赖氨酸）的潜在优势的洞察，以显着提高使用手性阴离子表面活性剂作为毛细管电泳中的假静脉期时对硼基衍生物的手性识别。

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