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

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.

Keywords: Chiralpak IC; bedaquiline analogues; diastereoseparation; separation mechanism; thermodynamic study.

MeSH terms

  • 2-Propanol / chemistry
  • Cellulose / analogs & derivatives
  • Cellulose / chemistry
  • Chromatography, High Pressure Liquid / methods*
  • Diarylquinolines / chemistry*
  • Diarylquinolines / isolation & purification*
  • Ethanol / chemistry
  • Phenylcarbamates / chemistry
  • Polysaccharides / chemistry
  • Stereoisomerism
  • Temperature

Substances

  • Diarylquinolines
  • Phenylcarbamates
  • Polysaccharides
  • cellulose tris(3,5-dichlorophenylcarbamate)
  • Ethanol
  • bedaquiline
  • Cellulose
  • 2-Propanol