Comparison of column performances in direct high-performance liquid chromatographic enantioseparation of 1- or 3-methyl-substituted tetrahydroisoquinoline analogs. Application of direct and indirect methods

A. Péter, Mária Péter, I. Ilisz, F. Fülöp

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The enantioseparability of 1- or 3-methyl-substituted tetrahydroisoquinolines was investigated by direct and indirect high-performance liquid chromatography. α- and β-cyclodextrin-, macrocyclic glycopeptide- and cellulose-based chiral columns and isothiocyanate- and Sanger-type chiral derivatizing agents (CDAs) were applied to attain satisfactory enantioseparation. Of the chiral columns, β-cyclodextrin-, vancomycin- and teicoplanin-containing macrocyclic glycopeptide-based columns appeared to be most suitable; of the CDAs, (1S,2R)-1-acetoxy-1-phenyl-2-propyl isothiocyanate was most favorable. The differences between the selectivities of the columns and CDAs were compared and optimized to yield the best resolution.

Original languageEnglish
Pages (from-to)459-465
Number of pages7
JournalBiomedical Chromatography
Volume19
Issue number6
DOIs
Publication statusPublished - Jul 2005

Fingerprint

Tetrahydroisoquinolines
Glycopeptides
Cyclodextrins
Teicoplanin
Liquids
Vancomycin
Cellulose
High Pressure Liquid Chromatography
High performance liquid chromatography
isothiocyanic acid

Keywords

  • Direct and indirect chiral separation
  • Salsolinol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Pharmacology

Cite this

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abstract = "The enantioseparability of 1- or 3-methyl-substituted tetrahydroisoquinolines was investigated by direct and indirect high-performance liquid chromatography. α- and β-cyclodextrin-, macrocyclic glycopeptide- and cellulose-based chiral columns and isothiocyanate- and Sanger-type chiral derivatizing agents (CDAs) were applied to attain satisfactory enantioseparation. Of the chiral columns, β-cyclodextrin-, vancomycin- and teicoplanin-containing macrocyclic glycopeptide-based columns appeared to be most suitable; of the CDAs, (1S,2R)-1-acetoxy-1-phenyl-2-propyl isothiocyanate was most favorable. The differences between the selectivities of the columns and CDAs were compared and optimized to yield the best resolution.",
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T1 - Comparison of column performances in direct high-performance liquid chromatographic enantioseparation of 1- or 3-methyl-substituted tetrahydroisoquinoline analogs. Application of direct and indirect methods

AU - Péter, A.

AU - Péter, Mária

AU - Ilisz, I.

AU - Fülöp, F.

PY - 2005/7

Y1 - 2005/7

N2 - The enantioseparability of 1- or 3-methyl-substituted tetrahydroisoquinolines was investigated by direct and indirect high-performance liquid chromatography. α- and β-cyclodextrin-, macrocyclic glycopeptide- and cellulose-based chiral columns and isothiocyanate- and Sanger-type chiral derivatizing agents (CDAs) were applied to attain satisfactory enantioseparation. Of the chiral columns, β-cyclodextrin-, vancomycin- and teicoplanin-containing macrocyclic glycopeptide-based columns appeared to be most suitable; of the CDAs, (1S,2R)-1-acetoxy-1-phenyl-2-propyl isothiocyanate was most favorable. The differences between the selectivities of the columns and CDAs were compared and optimized to yield the best resolution.

AB - The enantioseparability of 1- or 3-methyl-substituted tetrahydroisoquinolines was investigated by direct and indirect high-performance liquid chromatography. α- and β-cyclodextrin-, macrocyclic glycopeptide- and cellulose-based chiral columns and isothiocyanate- and Sanger-type chiral derivatizing agents (CDAs) were applied to attain satisfactory enantioseparation. Of the chiral columns, β-cyclodextrin-, vancomycin- and teicoplanin-containing macrocyclic glycopeptide-based columns appeared to be most suitable; of the CDAs, (1S,2R)-1-acetoxy-1-phenyl-2-propyl isothiocyanate was most favorable. The differences between the selectivities of the columns and CDAs were compared and optimized to yield the best resolution.

KW - Direct and indirect chiral separation

KW - Salsolinol

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