Cyclodextrin-mediated capillary electrophoresis enantioseparation of dansylated β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures

Henrik Harnisch, I. Ilisz, F. Fülöp, Z. Szakonyi, L. Kiss, A. Péter, Gerhard K.E. Scriba

Research output: Article

1 Citation (Scopus)

Abstract

The present study investigated the separation of bicyclic β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures by capillary electrophoresis using native cyclodextrins as well as neutral and charged derivatives as chiral selectors. The amino acids were derivatized with dansyl chloride to provide a UV chromophore. Separations were carried out at 20°C in a 48.5/40 cm, 50 μm fused-silica capillary at an applied voltage of 20 kV. Fifty millimolar sodium phosphate background electrolytes pH 2.5 and 7.2 containing either 5 or 30 mg/mL of the CDs were used. For the majority of the investigated CDs, enantioseparations could only be achieved at pH 2.5 when the analytes are positively charged. Successful enantioseparations as negatively charged analytes at pH 7.2 were only observed for few compounds. In the case of methyl-γ-cyclodextrin, opposite enantiomer migration order was observed in pH 2.5 or 7.2 background electrolytes. Dependence of the enantiomer migration order on the size of the cavity of the cyclodextrins was also found. Furthermore, the degree of methylation of β-cyclodextrin derivatives affected the migration order of several analyte enantiomers.

Original languageEnglish
JournalElectrophoresis
DOIs
Publication statusPublished - jan. 1 2019

Fingerprint

Oxazoles
Heptanes
Capillary electrophoresis
Cyclodextrins
Capillary Electrophoresis
Enantiomers
Amino Acids
Electrolytes
Methylation
Fused silica
Chromophores
Silicon Dioxide
Derivatives
bicyclo(2.2.2)octane
Electric potential

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

Cite this

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title = "Cyclodextrin-mediated capillary electrophoresis enantioseparation of dansylated β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures",
abstract = "The present study investigated the separation of bicyclic β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures by capillary electrophoresis using native cyclodextrins as well as neutral and charged derivatives as chiral selectors. The amino acids were derivatized with dansyl chloride to provide a UV chromophore. Separations were carried out at 20°C in a 48.5/40 cm, 50 μm fused-silica capillary at an applied voltage of 20 kV. Fifty millimolar sodium phosphate background electrolytes pH 2.5 and 7.2 containing either 5 or 30 mg/mL of the CDs were used. For the majority of the investigated CDs, enantioseparations could only be achieved at pH 2.5 when the analytes are positively charged. Successful enantioseparations as negatively charged analytes at pH 7.2 were only observed for few compounds. In the case of methyl-γ-cyclodextrin, opposite enantiomer migration order was observed in pH 2.5 or 7.2 background electrolytes. Dependence of the enantiomer migration order on the size of the cavity of the cyclodextrins was also found. Furthermore, the degree of methylation of β-cyclodextrin derivatives affected the migration order of several analyte enantiomers.",
keywords = "Cyclodextrin, Enantiomer migration order, Enantioseparation, β-Amino acid",
author = "Henrik Harnisch and I. Ilisz and F. F{\"u}l{\"o}p and Z. Szakonyi and L. Kiss and A. P{\'e}ter and Scriba, {Gerhard K.E.}",
year = "2019",
month = "1",
day = "1",
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T1 - Cyclodextrin-mediated capillary electrophoresis enantioseparation of dansylated β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures

AU - Harnisch, Henrik

AU - Ilisz, I.

AU - Fülöp, F.

AU - Szakonyi, Z.

AU - Kiss, L.

AU - Péter, A.

AU - Scriba, Gerhard K.E.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The present study investigated the separation of bicyclic β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures by capillary electrophoresis using native cyclodextrins as well as neutral and charged derivatives as chiral selectors. The amino acids were derivatized with dansyl chloride to provide a UV chromophore. Separations were carried out at 20°C in a 48.5/40 cm, 50 μm fused-silica capillary at an applied voltage of 20 kV. Fifty millimolar sodium phosphate background electrolytes pH 2.5 and 7.2 containing either 5 or 30 mg/mL of the CDs were used. For the majority of the investigated CDs, enantioseparations could only be achieved at pH 2.5 when the analytes are positively charged. Successful enantioseparations as negatively charged analytes at pH 7.2 were only observed for few compounds. In the case of methyl-γ-cyclodextrin, opposite enantiomer migration order was observed in pH 2.5 or 7.2 background electrolytes. Dependence of the enantiomer migration order on the size of the cavity of the cyclodextrins was also found. Furthermore, the degree of methylation of β-cyclodextrin derivatives affected the migration order of several analyte enantiomers.

AB - The present study investigated the separation of bicyclic β-amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures by capillary electrophoresis using native cyclodextrins as well as neutral and charged derivatives as chiral selectors. The amino acids were derivatized with dansyl chloride to provide a UV chromophore. Separations were carried out at 20°C in a 48.5/40 cm, 50 μm fused-silica capillary at an applied voltage of 20 kV. Fifty millimolar sodium phosphate background electrolytes pH 2.5 and 7.2 containing either 5 or 30 mg/mL of the CDs were used. For the majority of the investigated CDs, enantioseparations could only be achieved at pH 2.5 when the analytes are positively charged. Successful enantioseparations as negatively charged analytes at pH 7.2 were only observed for few compounds. In the case of methyl-γ-cyclodextrin, opposite enantiomer migration order was observed in pH 2.5 or 7.2 background electrolytes. Dependence of the enantiomer migration order on the size of the cavity of the cyclodextrins was also found. Furthermore, the degree of methylation of β-cyclodextrin derivatives affected the migration order of several analyte enantiomers.

KW - Cyclodextrin

KW - Enantiomer migration order

KW - Enantioseparation

KW - β-Amino acid

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