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高效液相色谱法在手性固定相上拆分八种贝达喹啉类似物的对映异构体。

Separation of eight bedaquiline analogue diastereomers by HPLC on an immobilized polysaccharide-based chiral stationary phase.

机构信息

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P. R. China.

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, P. R. China.

出版信息

Chirality. 2019 Jan;31(1):72-78. doi: 10.1002/chir.23037. Epub 2018 Dec 4.

Abstract

The high-performance liquid chromatography (HPLC) is a powerful method in the area of stereoisomer separation. In this study, separation of eight bedaquiline analogue diastereomers (compounds 1-8) was first examined on a cellulose tris-(3,5-dichlorophenylcarbamate) chiral stationary phase, ie, Chiralpak IC in the normal phase mode. The influences of organic modifier types, alcohol content, and column temperature on diastereoseparation were evaluated. Under the optimum chromatographic conditions, all the analyte stereoisomers were successfully separated. The experimental results revealed the great influence of analytes' structures on the diastereoseparation with Chiralpak IC. In addition, thermodynamic parameters were calculated by Van't Hoff plots, and correlative chiral recognition mechanisms were discussed further.

摘要

高效液相色谱(HPLC)是立体异构体分离领域的一种强大方法。在这项研究中,首次在纤维素三(3,5-二氯苯基氨基甲酸酯)手性固定相(即 Chiralpak IC)上以正相模式研究了八种贝达喹啉类似物非对映异构体(化合物 1-8)的分离。评估了有机溶剂类型、醇含量和柱温对非对映异构体分离的影响。在最佳色谱条件下,所有分析物的立体异构体都得到了成功分离。实验结果表明,Chiralpak IC 对非对映异构体的分离受分析物结构的影响很大。此外,通过 Van't Hoff 图计算了热力学参数,并进一步讨论了相关的手性识别机制。

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