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Micellar liquid chromatographic green enantioseparation of racemic amino alcohols and determination of elution order.
Biomedical Chromatography ( IF 1.8 ) Pub Date : 2020-07-24 , DOI: 10.1002/bmc.4954
Vijay Alwera 1 , Suman Sehlangia 2 , Shiv Alwera 1, 3
Affiliation  

A micellar liquid chromatographic method was developed for the green enantioseparation of racemic amino alcohols using an aqueous solution of the mixed surfactants as an alternative for organic solvents. In this study, the derivatives of the amino alcohols were synthesized using highly reactive chiral esters of (S)‐levofloxacin (Lfx) under microwave conditions, and an aqueous solution of the surfactants (Brij‐35 and SDS) was used for the enantioseparation of the synthesized diastereomeric derivatives (DDs) of amino alcohols using reversed‐phase HPLC. The activated ester of Lfx was synthesized by reacting with N‐hydroxybenzotriazole and characterized using UV, IR, 1H NMR, high‐resolution mass spectrometry, and elemental analysis. The DDs of racemic amino alcohols were separated on a C18 column using micellar LC. Chromatographic conditions were optimized by varying the concentration of the surfactants in aqueous solution and by varying the concentration and pH of the buffer. The green assessment score was calculated for the developed method (score: 82, an excellent green method). In addition, the density functional theory calculations were performed to develop the lowest energy‐optimized structures of DDs. The method was validated according to the International Conference of Harmonization guidelines, and the retention factor (k), selectivity factor (α), resolution factor (RS), limit of detection (0.198 ng mL−1 or 0.291 pM mL−1), and limit of quantification (0.594 ng mL−1 or 0.873 pM mL−1) were calculated.

中文翻译:

外消旋氨基醇的胶束液相色谱绿色对映体分离和洗脱顺序的确定。

开发了一种胶束液相色谱法,使用混合表面活性剂的水溶液作为有机溶剂的替代物,用于消旋氨基醇的绿色对映体分离。在这项研究中,使用(S)-左氧氟沙星(Lfx)的高反应性手性酯在微波条件下合成了氨基醇的衍生物,并使用表面活性剂(Brij-35和SDS)的水溶液对映体分离使用反相HPLC合成氨基醇的非对映异构体衍生物(DDs)。Lfx的活化酯是通过与N-羟基苯并三唑反应合成的,并使用UV,IR,11 H NMR,高分辨率质谱和元素分析。使用胶束LC在C 18色谱柱上分离外消旋氨基醇的DDs。通过改变水溶液中表面活性剂的浓度以及改变缓冲液的浓度和pH来优化色谱条件。针对已开发的方法计算绿色评估得分(得分:82,一种出色的绿色方法)。此外,进行了密度泛函理论计算,以开发出最低能量优化的DDs结构。该方法已根据国际协调会议指南进行了验证,保留因子(k),选择性因子(α),分离度因子(R S)),检测限(0.198 ng mL -1或0.291 pM mL -1)和定量限(0.594 ng mL -1或0.873 pM mL -1)。
更新日期:2020-07-24
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