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

被引:9
作者
Jiang, Shenmeng [1 ]
Wu, Chengjun [1 ]
Yu, Jia [1 ]
Sun, Tiemin [2 ]
Guo, Xingjie [1 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Pharm, 103 Wenhua Rd, Shenyang 110016, Liaoning, Peoples R China
[2] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang, Liaoning, Peoples R China
关键词
bedaquiline analogues; Chiralpak IC; diastereoseparation; separation mechanism; thermodynamic study; CHROMATOGRAPHY; RESOLUTION;
D O I
10.1002/chir.23037
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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.
引用
收藏
页码:72 / 78
页数:7
相关论文
共 29 条
[1]  
Amini A, 2001, ELECTROPHORESIS, V22, P3107, DOI 10.1002/1522-2683(200109)22:15<3107::AID-ELPS3107>3.0.CO
[2]  
2-Z
[3]   Acquired Resistance of Mycobacterium tuberculosis to Bedaquiline [J].
Andries, Koen ;
Villellas, Cristina ;
Coeck, Nele ;
Thys, Kim ;
Gevers, Tom ;
Vranckx, Luc ;
Lounis, Nacer ;
de Jong, Bouke C. ;
Koul, Anil .
PLOS ONE, 2014, 9 (07)
[4]   Chiral stationary phases for HPLC - Choosing the right stationary phase can be daunting. [J].
Armstrong, DW ;
Zhang, B .
ANALYTICAL CHEMISTRY, 2001, 73 (19) :557A-561A
[5]  
Chawla G, 2014, CURR MED RES PRACT, V4, P233
[6]   Pharmaceutical-enantiomers resolution using immobilized polysaccharide-based chiral stationary phases in supercritical fluid chromatography [J].
De Klerck, Katrijn ;
Vander Heyden, Yvan ;
Mangelings, Debby .
JOURNAL OF CHROMATOGRAPHY A, 2014, 1328 :85-97
[7]  
Doua M, 2016, J CHROMATOGR SCI, V54, P1
[8]   Direct chiral separations of the enantiomers of phenylpyrazole pesticides and the metabolites by HPLC [J].
Gao, Jing ;
Qu, Han ;
Zhang, Chuntao ;
Li, Weijia ;
Wang, Peng ;
Zhou, Zhiqiang .
CHIRALITY, 2017, 29 (01) :19-25
[9]   Thermodynamic and kinetic study of chiral separations of coumarin-based anticoagulants on derivatized amylose stationary phase [J].
Gebreyohannes, Kahsay G. ;
McGuffin, Victoria L. .
JOURNAL OF CHROMATOGRAPHY A, 2010, 1217 (38) :5901-5912
[10]   Enantioselective separation of racemates using CHIRALPAK IG amylose-based chiral stationary phase under normal standard, non-standard and reversed phase high performance liquid chromatography [J].
Ghanem, Ashraf ;
Wang, Chexu .
JOURNAL OF CHROMATOGRAPHY A, 2018, 1532 :89-97