Chiral Separation of Deprenyl-N-Oxide Isomers by Capillary Electrophoresis Using Various Cyclodextrin Derivatives

T. Tábi, Attila Sándor Halász, Melinda Pálfi, K. Magyar, É. Szökő

Research output: Contribution to journalArticle

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Abstract

Chiral separation of deprenyl-N-oxide isomers is presented using capillary electrophoresis in the presence of various cyclodextrin (CD) derivatives. This recently identified metabolite of R-(-)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substituents of the CD are examined on the enantiomer resolution of the compound having an asymmetric center on a heteroatom. The importance of hydrophilic or hydrogen bonding interaction, as well as the position of the interacting groups is demonstrated. Outstanding selectivity and resolution values are achieved using the chargeable carboxymethyl-β-CD. 2-Hydroxypropyl-β-CD is also suitable for the enantiomer separation of the analyte. Native β-CD and carboxyethyl-β-CD provide only poor enantioselectivity, whereas heptakis-(2,6-di-O-methyl)-β-CD is capable of separating only the diastereomers. No chiral resolution can be observed in the presence of γ-CD.

Original languageEnglish
Pages (from-to)21-26
Number of pages6
JournalJournal of Chromatographic Science
Volume42
Issue number1
Publication statusPublished - Jan 2004

Fingerprint

Capillary electrophoresis
Cyclodextrins
Capillary Electrophoresis
Isomers
Enantiomers
Selegiline
deprenyl-N-oxide
Enantioselectivity
Hydrogen Bonding
Metabolites
Hydrogen bonds
Pharmacology

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

Chiral Separation of Deprenyl-N-Oxide Isomers by Capillary Electrophoresis Using Various Cyclodextrin Derivatives. / Tábi, T.; Halász, Attila Sándor; Pálfi, Melinda; Magyar, K.; Szökő, É.

In: Journal of Chromatographic Science, Vol. 42, No. 1, 01.2004, p. 21-26.

Research output: Contribution to journalArticle

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AB - Chiral separation of deprenyl-N-oxide isomers is presented using capillary electrophoresis in the presence of various cyclodextrin (CD) derivatives. This recently identified metabolite of R-(-)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substituents of the CD are examined on the enantiomer resolution of the compound having an asymmetric center on a heteroatom. The importance of hydrophilic or hydrogen bonding interaction, as well as the position of the interacting groups is demonstrated. Outstanding selectivity and resolution values are achieved using the chargeable carboxymethyl-β-CD. 2-Hydroxypropyl-β-CD is also suitable for the enantiomer separation of the analyte. Native β-CD and carboxyethyl-β-CD provide only poor enantioselectivity, whereas heptakis-(2,6-di-O-methyl)-β-CD is capable of separating only the diastereomers. No chiral resolution can be observed in the presence of γ-CD.

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