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, A. Gömöry, Cs Szántay, J. Fekete

Research output: Contribution to journalArticle

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 - 2004

Fingerprint

Carbolines
Enantiomers
Chromatography
High Pressure Liquid Chromatography
Derivatives
Reverse-Phase Chromatography
Solubility
Noise

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

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title = "Preparation and separation of 1-methyl-1,2,3,4-tetrahydro-β-carboline enantiomers by HPLC using a new derivatization reagent",
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.",
keywords = "β-Carbolines, Asymmetric induction, Column liquid chromatography, Diastereomeric derivatives",
author = "M. Milen and L. Hazai and P. Kolonits and A. G{\"o}m{\"o}ry and Cs Sz{\'a}ntay and J. Fekete",
year = "2004",
doi = "10.1081/JLC-200030844",
language = "English",
volume = "27",
pages = "2921--2933",
journal = "Journal of Liquid Chromatography and Related Technologies",
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publisher = "Taylor and Francis Ltd.",
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TY - JOUR

T1 - Preparation and separation of 1-methyl-1,2,3,4-tetrahydro-β-carboline enantiomers by HPLC using a new derivatization reagent

AU - Milen, M.

AU - Hazai, L.

AU - Kolonits, P.

AU - Gömöry, A.

AU - Szántay, Cs

AU - Fekete, J.

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - β-Carbolines

KW - Asymmetric induction

KW - Column liquid chromatography

KW - Diastereomeric derivatives

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U2 - 10.1081/JLC-200030844

DO - 10.1081/JLC-200030844

M3 - Article

VL - 27

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JO - Journal of Liquid Chromatography and Related Technologies

JF - Journal of Liquid Chromatography and Related Technologies

SN - 1082-6076

IS - 18

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