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 2003

Fingerprint

High Pressure Liquid Chromatography
Derivatives
Carbolines
Diacetyl
Molecular mechanics
Stereoisomerism
Alkaloids
Rigidity
Electron energy levels
Esters
Mechanics

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

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

Comparative study on separation of diastereomers by HPLC. / Fekete, J.; Milen, M.; Hazai, L.; Poppe, L.; Szántay, Cs; Kettrup, A.; Gebefügi, I.

In: Chromatographia, Vol. 57, No. 3-4, 02.2003, p. 147-153.

Research output: Contribution to journalArticle

Fekete, J, Milen, M, Hazai, L, Poppe, L, Szántay, C, Kettrup, A & Gebefügi, I 2003, 'Comparative study on separation of diastereomers by HPLC', Chromatographia, vol. 57, no. 3-4, pp. 147-153. https://doi.org/10.1007/BF02491708
Fekete, J. ; Milen, M. ; Hazai, L. ; Poppe, L. ; Szántay, Cs ; Kettrup, A. ; Gebefügi, I. / Comparative study on separation of diastereomers by HPLC. In: Chromatographia. 2003 ; Vol. 57, No. 3-4. pp. 147-153.
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