Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases

Anita Aranyi, I. Ilisz, Nóra Grecsó, Renáta Csütörtöki, I. Szatmári, F. Fülöp, A. Péter

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Abstract

The stereoisomers of ten unusual amino acid analogs, 1- and 2-naphthol-substituted glycine and its ester derivatives, were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-1), cellulose tris-(3-chloro-4-methylphenylcarbamate) (Cellulose-2), cellulose tris-(4-methylbenzoate) (Cellulose-3), cellulose tris-(4-chloro-3-methylphenylcarbamate) (Cellulose-4) and amylose tris-(5-chloro-2-methylphenylcarbamate) (Amylose-2). Experiments were performed in normal-phase mode with n-heptane/alcohol/diethylamine mobile phases in a wide temperature range: 5-50°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs. 1/T. Δ(ΔH°) ranged from -10.1 to 6.2kJmol-1, Δ(ΔS°) from -31.5 to 22.5Jmol-1K-1 and -Δ(ΔG°) from 0.4 to 1.4kJmol-1, and both enthalpy 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 some cases.

Original languageEnglish
Pages (from-to)183-191
Number of pages9
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume76
DOIs
Publication statusPublished - Mar 25 2013

Fingerprint

Stereoisomerism
Cellulose
Glycine
Polysaccharides
Esters
Temperature
Liquids
Entropy
Thermodynamics
Alcohols
Amino Acids
Enthalpy
Derivatives
Experiments
cellulose tris(4-methylbenzoate)
amylose-tris-(5-chloro-2-methylphenylcarbamate)
cellulose tris(4-chloro-3-methylphenylcarbamate)
n-heptane
diethylamine
tris(4-methylbenzoate)cellulose

Keywords

  • Column liquid chromatography
  • Enantiomer separation
  • Gly analogs
  • Lux Amylose-2 column
  • Lux Cellulose columns

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Spectroscopy
  • Clinical Biochemistry

Cite this

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title = "Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases",
abstract = "The stereoisomers of ten unusual amino acid analogs, 1- and 2-naphthol-substituted glycine and its ester derivatives, were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-1), cellulose tris-(3-chloro-4-methylphenylcarbamate) (Cellulose-2), cellulose tris-(4-methylbenzoate) (Cellulose-3), cellulose tris-(4-chloro-3-methylphenylcarbamate) (Cellulose-4) and amylose tris-(5-chloro-2-methylphenylcarbamate) (Amylose-2). Experiments were performed in normal-phase mode with n-heptane/alcohol/diethylamine mobile phases in a wide temperature range: 5-50°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs. 1/T. Δ(ΔH°) ranged from -10.1 to 6.2kJmol-1, Δ(ΔS°) from -31.5 to 22.5Jmol-1K-1 and -Δ(ΔG°) from 0.4 to 1.4kJmol-1, and both enthalpy 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 some cases.",
keywords = "Column liquid chromatography, Enantiomer separation, Gly analogs, Lux Amylose-2 column, Lux Cellulose columns",
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TY - JOUR

T1 - Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases

AU - Aranyi, Anita

AU - Ilisz, I.

AU - Grecsó, Nóra

AU - Csütörtöki, Renáta

AU - Szatmári, I.

AU - Fülöp, F.

AU - Péter, A.

PY - 2013/3/25

Y1 - 2013/3/25

N2 - The stereoisomers of ten unusual amino acid analogs, 1- and 2-naphthol-substituted glycine and its ester derivatives, were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-1), cellulose tris-(3-chloro-4-methylphenylcarbamate) (Cellulose-2), cellulose tris-(4-methylbenzoate) (Cellulose-3), cellulose tris-(4-chloro-3-methylphenylcarbamate) (Cellulose-4) and amylose tris-(5-chloro-2-methylphenylcarbamate) (Amylose-2). Experiments were performed in normal-phase mode with n-heptane/alcohol/diethylamine mobile phases in a wide temperature range: 5-50°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs. 1/T. Δ(ΔH°) ranged from -10.1 to 6.2kJmol-1, Δ(ΔS°) from -31.5 to 22.5Jmol-1K-1 and -Δ(ΔG°) from 0.4 to 1.4kJmol-1, and both enthalpy 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 some cases.

AB - The stereoisomers of ten unusual amino acid analogs, 1- and 2-naphthol-substituted glycine and its ester derivatives, were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-1), cellulose tris-(3-chloro-4-methylphenylcarbamate) (Cellulose-2), cellulose tris-(4-methylbenzoate) (Cellulose-3), cellulose tris-(4-chloro-3-methylphenylcarbamate) (Cellulose-4) and amylose tris-(5-chloro-2-methylphenylcarbamate) (Amylose-2). Experiments were performed in normal-phase mode with n-heptane/alcohol/diethylamine mobile phases in a wide temperature range: 5-50°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs. 1/T. Δ(ΔH°) ranged from -10.1 to 6.2kJmol-1, Δ(ΔS°) from -31.5 to 22.5Jmol-1K-1 and -Δ(ΔG°) from 0.4 to 1.4kJmol-1, and both enthalpy 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 some cases.

KW - Column liquid chromatography

KW - Enantiomer separation

KW - Gly analogs

KW - Lux Amylose-2 column

KW - Lux Cellulose columns

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U2 - 10.1016/j.jpba.2012.12.030

DO - 10.1016/j.jpba.2012.12.030

M3 - Article

VL - 76

SP - 183

EP - 191

JO - Journal of Pharmaceutical and Biomedical Analysis

JF - Journal of Pharmaceutical and Biomedical Analysis

SN - 0731-7085

ER -