Preparation and separation of 1-methyl-1,2,3,4-tetrahydro-β-carboline enantiomers by HPLC using a new derivatization reagent

M. Milen, L. Hazai, P. Kolonits, Á Gömöry, Cs Szántay, J. Fekete

Research output: Article

1 Citation (Scopus)

Abstract

1-Methyl-3,4-dihydro-β-carboline (1) was C-acylated with optically active sulfinyl derivatives (2) into the 1-methyl group. Reduction of the C=N double bond resulted in diastereomers (4, 5) of different ratios. After separation of diastereomers and removal of the chiral sulfinyl moiety, enantiomers of 1-methyl-1,2,3,4-tetrahydro-β-carboline (6) were obtained from different enantiomeric excess. The diastereomers were separated by normal phase chromatography. It was proven that the resolution efficiency was much better with this type of separation method compared with very popular reversed phase chromatography. Embedded reversed phase column (Supelcosil ABZ + Plus) gave higher resolution than conventional C-18 stationary phases and monoliths (Chromolith Performance RP-18e), but retention time is high and low solubilities of derivatives caused detection problems and base line noise.

Original languageEnglish
Pages (from-to)2921-2933
Number of pages13
JournalJournal of Liquid Chromatography and Related Technologies
Volume27
Issue number18
DOIs
Publication statusPublished - okt. 25 2004

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Pharmaceutical Science
  • Clinical Biochemistry

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