Comparative study on separation of diastereomers by HPLC

J. Fekete, M. Milen, L. Hazai, L. Poppe, Cs Szántay, A. Kettrup, I. Gebefügi

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Reversed (RP-HPLC) and normal phase chromatographic (NP-HPLC) separations have been developed for diastereomers of N-acyl-1-methyl-1,2,3,4-tetrahydo-β-carbolines which are acylated derivatives of simple natural β-carboline alkaloids. Separations of derivatives having different acyl moieties in the O,O-diacyl-tartaric acid ester subtituent differed remarkably. Little or no resolution in either NP-HPLC or RP-HPLC could be achieved with the diacetyl-tartrate derivative. Base-line separation by RP-HPLC but no separation by NP-HPLC was possible with the bulkier and more apolar dipivaloyl derivative. Retention order of the bis-benzoylated diastereomers was reversed and separation time increased dramatically by RP-HPLC. Good separation of the medium polarity, but rigid, N-camphanyl derivative by NP-HPLC has been achieved, whereas RP-HPLC could not be used for separation of these diastereomers. Separability of different diastereomers was highly dependent on polarity and rigidity of the derivatizing N-acyl moieties. Conformational analysis by molecular mechanics and comparison of the lowest energy conformational states of the diastereomers was applied to rationalise separation-retention behaviour of stereoisomers by RP-HPLC.

Original languageEnglish
Pages (from-to)147-153
Number of pages7
JournalChromatographia
Volume57
Issue number3-4
DOIs
Publication statusPublished - Feb 1 2003

Keywords

  • Asymmetric induction
  • Column liquid chromatography
  • Conformational analysis
  • Diastereomeric derivatives
  • β-Carbolines

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Fekete, J., Milen, M., Hazai, L., Poppe, L., Szántay, C., Kettrup, A., & Gebefügi, I. (2003). Comparative study on separation of diastereomers by HPLC. Chromatographia, 57(3-4), 147-153. https://doi.org/10.1007/BF02491708