Enhanced enantioselective separation of racemic menthol via reverse-phase high-performance liquid chromatography: Method development and computational insights for pre-screening.

IF 5.6 1区化学 Q1 CHEMISTRY, ANALYTICAL Talanta Pub Date : 2025-01-01 Epub Date: 2024-10-17 DOI:10.1016/j.talanta.2024.127062

Haifang Mao, Yucheng Zhou, Zhengyang Xu, Yun Zhao

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Abstract

A robust and efficient enantioselective separation of racemic menthol was achieved on a standard C₁₈ column with reverse-phase high-performance liquid chromatography (RP-HPLC) and UV detector. (R)-α-hydroxy-4-methylbenzeneacetic acid was utilized as the pre-column derivatization reagent. The impact of mobile phase composition on diastereomer selectivity was thoroughly investigated, resulting in a high resolution of 2.11 under optimized conditions. The method was rigorously validated for linearity, precision, accuracy, limit of detection (LOD) and limit of quantification (LOQ). Notably, a separation pre-screening mechanism (SPM) and a prediction model was developed based on density functional theory (DFT) studies. This model elucidated the relationship between molecular polarity differences (△MPI) and chromatographic behavior, facilitating the interpretation and prediction of racemic menthol resolution with various chiral derivatization reagents. The present work not only presents an efficient and economical approach for menthol enantiomeric separation, but also offers valuable insights for the innovative design and advancement of chromatographic methodologies for a wide array of chiral enantiomers.

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通过反相高效液相色谱法增强外消旋薄荷醇的对映体选择性分离：用于预筛选的方法开发和计算见解。

采用标准 C18 色谱柱、反相高效液相色谱法（RP-HPLC）和紫外检测器，实现了外消旋薄荷醇的可靠、高效对映体选择性分离。柱前衍生试剂为(R)-α-羟基-4-甲基苯乙酸。对流动相组成对非对映异构体选择性的影响进行了深入研究，结果表明，在优化条件下，该方法的分辨率高达 2.11。该方法在线性、精密度、准确度、检出限（LOD）和定量限（LOQ）方面都得到了严格验证。值得注意的是，基于密度泛函理论（DFT）研究建立了分离预筛机制（SPM）和预测模型。该模型阐明了分子极性差异（△MPI）与色谱行为之间的关系，有助于解释和预测外消旋薄荷醇与各种手性衍生试剂的分离。本研究不仅提出了一种高效、经济的薄荷醇对映体分离方法，还为创新设计和改进各种手性对映体的色谱方法提供了宝贵的见解。

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来源期刊

Talanta 化学-分析化学

CiteScore

12.30

自引率

4.90%

发文量

861

审稿时长

29 days

期刊介绍： Talanta provides a forum for the publication of original research papers, short communications, and critical reviews in all branches of pure and applied analytical chemistry. Papers are evaluated based on established guidelines, including the fundamental nature of the study, scientific novelty, substantial improvement or advantage over existing technology or methods, and demonstrated analytical applicability. Original research papers on fundamental studies, and on novel sensor and instrumentation developments, are encouraged. Novel or improved applications in areas such as clinical and biological chemistry, environmental analysis, geochemistry, materials science and engineering, and analytical platforms for omics development are welcome. Analytical performance of methods should be determined, including interference and matrix effects, and methods should be validated by comparison with a standard method, or analysis of a certified reference material. Simple spiking recoveries may not be sufficient. The developed method should especially comprise information on selectivity, sensitivity, detection limits, accuracy, and reliability. However, applying official validation or robustness studies to a routine method or technique does not necessarily constitute novelty. Proper statistical treatment of the data should be provided. Relevant literature should be cited, including related publications by the authors, and authors should discuss how their proposed methodology compares with previously reported methods.