{"title":"Preparation of Chiral Stationary Phase Based on 1,1'-bi-2-Naphthol for Chiral Enantiomer Separation.","authors":"Kun Fan, Rui Dong, Wenqing Hou, Canyu Yang, Kongchun Sun, LvJing Xu, Bingquan Chang, Desheng Wang, Congcong Zhang, Baochun Shen","doi":"10.1093/chromsci/bmae051","DOIUrl":null,"url":null,"abstract":"<p><p>Two enantiomeric novel chiral stationary phases (CSPs) R-3-Amide-BINOL CSP (CSP-1) and S-3-Amide-BINOL CSP (CSP-2) were prepared using (R/S)-1,1'-bi-2-naphthol (BINOL) derivatives as chiral selectors. The structure of CSPs was characterized by nuclear magnetic resonance, scanning electron microscope and elemental analysis. Four chiral solutes were selected under normal phase HPLC conditions to evaluate the chiral separation ability of the two novel CSPs. The effects of mobile phase and acidic additives on enantiomeric separation were investigated. The combination of molecular docking simulation and experimental data has elucidated the crucial role of hydrogen bonds and π-π interactions formed between the analyte and CSP in chiral recognition, and different configurations of CSP can cause enantiomeric elution sequence reversal, indicating that the configuration of chiral selectors in CSP has a significant impact on chiral recognition ability.</p>","PeriodicalId":15430,"journal":{"name":"Journal of chromatographic science","volume":" ","pages":""},"PeriodicalIF":1.5000,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of chromatographic science","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1093/chromsci/bmae051","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMICAL RESEARCH METHODS","Score":null,"Total":0}
引用次数: 0
Abstract
Two enantiomeric novel chiral stationary phases (CSPs) R-3-Amide-BINOL CSP (CSP-1) and S-3-Amide-BINOL CSP (CSP-2) were prepared using (R/S)-1,1'-bi-2-naphthol (BINOL) derivatives as chiral selectors. The structure of CSPs was characterized by nuclear magnetic resonance, scanning electron microscope and elemental analysis. Four chiral solutes were selected under normal phase HPLC conditions to evaluate the chiral separation ability of the two novel CSPs. The effects of mobile phase and acidic additives on enantiomeric separation were investigated. The combination of molecular docking simulation and experimental data has elucidated the crucial role of hydrogen bonds and π-π interactions formed between the analyte and CSP in chiral recognition, and different configurations of CSP can cause enantiomeric elution sequence reversal, indicating that the configuration of chiral selectors in CSP has a significant impact on chiral recognition ability.
期刊介绍：
The Journal of Chromatographic Science is devoted to the dissemination of information concerning all methods of chromatographic analysis. The standard manuscript is a description of recent original research that covers any or all phases of a specific separation problem, principle, or method. Manuscripts which have a high degree of novelty and fundamental significance to the field of separation science are particularly encouraged. It is expected the authors will clearly state in the Introduction how their method compares in some markedly new and improved way to previous published related methods. Analytical performance characteristics of new methods including sensitivity, tested limits of detection or quantification, accuracy, precision, and specificity should be provided. Manuscripts which describe a straightforward extension of a known analytical method or an application to a previously analyzed and/or uncomplicated sample matrix will not normally be reviewed favorably. Manuscripts in which mass spectrometry is the dominant analytical method and chromatography is of marked secondary importance may be declined.
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