High-performance liquid chromatographic enantioseparation of amino alcohol analogues possessing 1,2,3,4-tetrahydroisoquinoline skeleton on polysaccharide-based chiral stationary phases

Nóra Grecsó, I. Ilisz, Zsanett Gecse, László Schönstein, F. Fülöp, A. Péter

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1 Citation (Scopus)

Abstract

The stereoisomers of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues and derivatives thereof were separated in normal-phase mode on chiral stationary phases based on preprepared silica coated with cellulose tris-(3,5-dimethylphenyl carbamate), cellulose tris-(3-chloro-4-methylphenyl carbamate), cellulose tris-(4-methylbenzoate) or cellulose tris-(4-chloro-3-methylphenyl carbamate). On all the investigated chiral columns, the retention and the enantioseparation were influenced by the nature and the concentrations of the mobile phase components and additives, and also the temperature. Experiments were performed in the temperature range 10-50°C. Thermodynamic parameters were calculated from plots of lnα vs 1/T. On these polysaccharide-based chiral columns, both enthalpy-driven separations and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature. The sequence of elution of the stereoisomers was determined in all cases.

Original languageEnglish
Pages (from-to)788-796
Number of pages9
JournalBiomedical Chromatography
Volume29
Issue number5
DOIs
Publication statusPublished - May 1 2015

Fingerprint

Amino Alcohols
Skeleton
Cellulose
Polysaccharides
Stereoisomerism
Carbamates
Temperature
Liquids
Entropy
Thermodynamics
Silicon Dioxide
Enthalpy
Derivatives
1,2,3,4-tetrahydroisoquinoline
Experiments

Keywords

  • Direct enantiomer separation of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues
  • High-performance liquid chromatography (HPLC)
  • Polysaccharide-based chiral stationary phases
  • Temperature dependence of chiral separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Pharmacology

Cite this

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title = "High-performance liquid chromatographic enantioseparation of amino alcohol analogues possessing 1,2,3,4-tetrahydroisoquinoline skeleton on polysaccharide-based chiral stationary phases",
abstract = "The stereoisomers of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues and derivatives thereof were separated in normal-phase mode on chiral stationary phases based on preprepared silica coated with cellulose tris-(3,5-dimethylphenyl carbamate), cellulose tris-(3-chloro-4-methylphenyl carbamate), cellulose tris-(4-methylbenzoate) or cellulose tris-(4-chloro-3-methylphenyl carbamate). On all the investigated chiral columns, the retention and the enantioseparation were influenced by the nature and the concentrations of the mobile phase components and additives, and also the temperature. Experiments were performed in the temperature range 10-50°C. Thermodynamic parameters were calculated from plots of lnα vs 1/T. On these polysaccharide-based chiral columns, both enthalpy-driven separations and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature. The sequence of elution of the stereoisomers was determined in all cases.",
keywords = "Direct enantiomer separation of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues, High-performance liquid chromatography (HPLC), Polysaccharide-based chiral stationary phases, Temperature dependence of chiral separation",
author = "N{\'o}ra Grecs{\'o} and I. Ilisz and Zsanett Gecse and L{\'a}szl{\'o} Sch{\"o}nstein and F. F{\"u}l{\"o}p and A. P{\'e}ter",
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T1 - High-performance liquid chromatographic enantioseparation of amino alcohol analogues possessing 1,2,3,4-tetrahydroisoquinoline skeleton on polysaccharide-based chiral stationary phases

AU - Grecsó, Nóra

AU - Ilisz, I.

AU - Gecse, Zsanett

AU - Schönstein, László

AU - Fülöp, F.

AU - Péter, A.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - The stereoisomers of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues and derivatives thereof were separated in normal-phase mode on chiral stationary phases based on preprepared silica coated with cellulose tris-(3,5-dimethylphenyl carbamate), cellulose tris-(3-chloro-4-methylphenyl carbamate), cellulose tris-(4-methylbenzoate) or cellulose tris-(4-chloro-3-methylphenyl carbamate). On all the investigated chiral columns, the retention and the enantioseparation were influenced by the nature and the concentrations of the mobile phase components and additives, and also the temperature. Experiments were performed in the temperature range 10-50°C. Thermodynamic parameters were calculated from plots of lnα vs 1/T. On these polysaccharide-based chiral columns, both enthalpy-driven separations and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature. The sequence of elution of the stereoisomers was determined in all cases.

AB - The stereoisomers of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues and derivatives thereof were separated in normal-phase mode on chiral stationary phases based on preprepared silica coated with cellulose tris-(3,5-dimethylphenyl carbamate), cellulose tris-(3-chloro-4-methylphenyl carbamate), cellulose tris-(4-methylbenzoate) or cellulose tris-(4-chloro-3-methylphenyl carbamate). On all the investigated chiral columns, the retention and the enantioseparation were influenced by the nature and the concentrations of the mobile phase components and additives, and also the temperature. Experiments were performed in the temperature range 10-50°C. Thermodynamic parameters were calculated from plots of lnα vs 1/T. On these polysaccharide-based chiral columns, both enthalpy-driven separations and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature. The sequence of elution of the stereoisomers was determined in all cases.

KW - Direct enantiomer separation of 1,2,3,4-tetrahydroisoquinoline amino alcohol analogues

KW - High-performance liquid chromatography (HPLC)

KW - Polysaccharide-based chiral stationary phases

KW - Temperature dependence of chiral separation

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