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Chromatographic enantioseparation and adsorption thermodynamics of hydroxy acids and their derivatives on antibiotic-based chiral stationary phases as affected by eluent pH
Chromatographia ( IF 1.7 ) Pub Date : 2020-11-15 , DOI: 10.1007/s10337-020-03978-w
Otar Sh. Gogolishvili , Elena N. Reshetova

The study was dedicated to retention regularities and adsorption thermodynamics of enantiomers of aromatic hydroxy acids and their derivatives on chiral stationary phases (CSPs) Nautilus-E, Nautilus-R and Chirobiotic T with antibiotics eremomycin, ristomycin and teicoplanin from water–ethanol eluents under conditions of linear liquid chromatography. The enantioselective properties of the chiral adsorbents under study were compared. The interrelationship between the structure of the adsorbates under study, the retention and separation selectivity of their enantiomers was evinced. Dissociation constants of hydroxy acids under study in aqueous ethanol solutions were determined. The dependences of retention, separation, and thermodynamic values’ characteristics vs. eluent pH were revealed. The retention mechanism of the hydroxy acid enantiomers was found out to vary with varying eluent pH. Ion–ion interactions were evinced to determine the retention and separation selectivity of hydroxy acid enantiomers on Nautilus-E and Nautilus-R CSPs, whereas nonionic interactions on Chirobiotic T CSP can play a key role. The enantioselectivity of Chirobiotic T CSP is first of all regulated by the anionic form of hydroxy acids. The retention and enantiorecognition mechanism on the Nautilus-E and Nautilus-R CSPs were revealed to be different. The retention mechanisms for S- and R-enantiomers were found out to be similar on both CSPs. On the Nautilus-E and Nautilus-R CSPs, a distinction between the adsorption mechanisms of the enantiomers of hydroxy acids and their esters was found out. On Nautilus-E, a distinction between the adsorption mechanisms of the enantiomers hydroxy acids with different lengths of the n-alkyl substituent in the side chain containing the stereogenic center was found out.

中文翻译:

羟基酸及其衍生物在抗生素手性固定相上的色谱对映分离和吸附热力学受洗脱液 pH 的影响

该研究致力于研究芳香羟基酸的对映异构体及其衍生物在手性固定相 (CSP) Nautilus-E、Nautilus-R 和 Chirobiotic T 上的保留规律和吸附热力学,其中抗生素埃雷姆霉素、里斯霉素和替考拉宁在条件下来自水-乙醇洗脱液线性液相色谱法。比较了所研究的手性吸附剂的对映选择性特性。所研究的被吸附物的结构、其对映体的保留和分离选择性之间的相互关系得到了证明。测定研究中的羟基酸在乙醇水溶液中的解离常数。揭示了保留、分离和热力学值的特性与洗脱液 pH 值的相关性。发现羟基酸对映异构体的保留机制随着洗脱液 pH 的变化而变化。离子-离子相互作用被证明可以确定羟基酸对映体在 Nautilus-E 和 Nautilus-R CSP 上的保留和分离选择性,而 Chirobiotic T CSP 上的非离子相互作用可以发挥关键作用。Chirobiotic T CSP 的对映选择性首先受阴离子形式的羟基酸的调节。揭示了 Nautilus-E 和 Nautilus-R CSP 上的保留和对映识别机制是不同的。发现 S 和 R 对映异构体的保留机制在两种 CSP 上相似。在 Nautilus-E 和 Nautilus-R CSP 上,发现了羟基酸及其酯对映异构体的吸附机制之间的区别。在鹦鹉螺-E上,
更新日期:2020-11-15
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