Centro de Química Medicinal da Universidade do Porto-CEQUIMED-UP, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal.
J Chromatogr A. 2012 Jun 8;1241:60-8. doi: 10.1016/j.chroma.2012.04.011. Epub 2012 Apr 11.
A chiral HPLC method using four macrocyclic antibiotic chiral stationary phases (CSPs) has been investigated for determination of the enantiomeric purity of fourteen new chiral derivatives of xanthones (CDXs). The separations were performed with the CSPs Chirobiotic T, Chirobiotic TAG, Chirobiotic V and Chirobiotic R under multimodal elution conditions (normal-phase, reversed-phase and polar ionic mode). The analyses were performed at room temperature in isocratic mode and UV and CD detection at a wavelength of 254 nm. The best enantioselectivity and resolution were achieved on Chirobiotic R and Chirobiotic T CSPs, under normal elution conditions, with R(S) ranging from 1.25 to 2.50 and from 0.78 to 2.06, respectively. The optimized chromatographic conditions allowed the determination of the enantiomeric ratio of eight CDXs, always higher than 99%. In order to better understand the chromatographic behavior at a molecular level, and the structural features associated with the chiral recognition mechanism, computational studies by molecular docking were carried out using VDock. These studies shed light on the mechanisms involved in the enantioseparation for this important class of chiral compounds.
一种手性 HPLC 方法使用了四种大环抗生素手性固定相 (CSPs)，用于测定十四种新的黄烷酮手性衍生物 (CDXs) 的对映体纯度。在多模态洗脱条件下（正相、反相和极性离子模式），使用 Chirobiotic T、Chirobiotic TAG、Chirobiotic V 和 Chirobiotic R 四种 CSP 进行分离。分析在室温下以等度模式进行，在 254nm 波长处进行 UV 和 CD 检测。在正相洗脱条件下，Chirobiotic R 和 Chirobiotic T CSPs 表现出最佳的对映选择性和分辨率，R(S) 值分别为 1.25 至 2.50 和 0.78 至 2.06。优化的色谱条件允许测定八种 CDXs 的对映体比例，始终高于 99%。为了更好地从分子水平理解色谱行为，以及与手性识别机制相关的结构特征，使用 VDock 进行了分子对接的计算研究。这些研究阐明了在手性化合物的这个重要类别中进行对映体分离的机制。
