Comparison of Chiral Recognition of Binaphthyl Derivatives with l-Undecyl-Leucine Surfactants in the Presence of Arginine and Sodium Counterions
Comparison of Chiral Recognition of Binaphthyl Derivatives with l-Undecyl-Leucine Surfactants in the Presence of Arginine and Sodium Counterions
复制标题
精氨酸和钠抗衡离子存在下联萘衍生物与 l-十一烷基亮氨酸表面活性剂手性识别的比较
DOI：
10.1093/chromsci/bmy080
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发表时间：
2018
影响因子：
1.3
通讯作者：
Fang, Yayin
中科院分区：
文献类型：
--
作者：
Ramos, Zoe;Rothbauer, Gabriel A;Turner, Johnathan;Lewis, Corbin;Morris, Kevin;Billiot, Eugene;Billiot, Fereshteh;Fang, Yayin
在这项研究中，在pH值为7至11的范围内，使用精氨酸和钠反离子检查了联萘衍生物对十一烷基亮氨酸（und-leu）的手性选择性。本项目的目的是研究阳离子氨基酸，如精氨酸，是否会实现增强的手性选择性时，作为抗衡在胶束电动色谱钠的地方。数据表明，与钠相比，在精氨酸抗衡离子存在下，und-leu对1，1 ′-联萘-2，2 ′-磷酸氢二酯（BNP）对映体的手性选择性显著提高，至少在本研究的情况下，精氨酸的对映体形式似乎在手性选择性中不起作用。当钠用作对照时，BNP达到的最大分辨率（Rs）约为0.6。然而，当使用精氨酸作为对照时，BNP的最大分辨率为~4.1。这是分辨率提高约7倍。而1，1 ′-联-2-萘酚的对映异构体没有观察到显著差异。为了更多地了解为什么会出现这种情况，进行了NMR研究，以检查反式异构体在对映体识别中可能发挥的作用。
In this study the chiral selectivity ofl-undecyl-leucine (und-leu) for binapthyl derivatives was examined with the use of arginine and sodium counterions at pH’s ranging from 7 to 11. The objective of this project was to investigate whether a cationic amino acid, such as arginine would achieve enhanced chiral selectivity when utilized as the counterion in the place of sodium in micellar electrokinetic chromatography. The data indicate that und-leu has significantly improved chiral selectivity toward 1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (BNP) enantiomers in the presence of arginine counterions in comparison to sodium and that, at least in the case of this study, the enantiomeric form of the arginine did not appear to play a role in the chiral selectivity. The maximum resolution (Rs) achieved for BNP when sodium was used as the counterion was ~0.6. However, when arginine was used as the counterion, the maximum resolution for BNP was ~4.1. This was an increase in resolution of ~ 7-fold. However, no significant difference was observed for the enantiomers of 1,1′-bi-2-naphthol. In order to learn more about why this might be the case, NMR studies were conducted to examine what role the counterion might play in enantiomeric recognition.