The role of π-acidic and π-basic chiral stationary phases in the high-performance liquid chromatographic enantioseparation of unusual β-amino acids

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Abstract

The application of 3,5-dimethylphenyl-carbamoylated-β-cyclodextrin (Cyclobond I 2000 DMP) and 2,6-dinitro-4-trifluoromethylphenyl-ether-β-cyclodextrin-based (Cyclobond DNP) chiral stationary phases for the high-performance liquid chromatographic enantioseparation of unusual β-amino acids is reported. The investigated amino acids were saturated or unsaturated alicyclic β-3-homo-amino acids and bicyclic β-amino acids. Prior to chromatographic analyses, all amino acids were transformed to N-3,5-dinitrobenzoyl- or N-3,5-dimethylbenzoyl form to ensure a π-acidic or π-basic function and to enhance the π-acidic-π-basic interactions between analytes and chiral selectors. Chromatographic results are given as retention, separation and resolution factors. The chromatographic conditions were varied to achieve optimal separation. The sequence of elution of the enantiomers was determined in some cases.

Original languageEnglish
Pages (from-to)339-348
Number of pages10
JournalChirality
Volume21
Issue number3
DOIs
Publication statusPublished - 2009

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Amino acids
Amino Acids
Liquids
Cyclodextrins
Enantiomers
Ether
Chromatography
Ethers

Keywords

  • 2,6-dinitro-4-trifluoromethylphenyl-ether-β-cyclodextrin-based column (Cyclobond DNP)
  • 3,5-dimethylphenyl-carbamoylated-β-cyclodextrin-based column (Cyclobond I 2000 DMP)
  • Bicyclic-β-amino acids
  • Chiral stationary phases (CSPs)
  • High-performance liquid chromatography (HPLC)
  • Unusual β-3-homo amino acids

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

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title = "The role of π-acidic and π-basic chiral stationary phases in the high-performance liquid chromatographic enantioseparation of unusual β-amino acids",
abstract = "The application of 3,5-dimethylphenyl-carbamoylated-β-cyclodextrin (Cyclobond I 2000 DMP) and 2,6-dinitro-4-trifluoromethylphenyl-ether-β-cyclodextrin-based (Cyclobond DNP) chiral stationary phases for the high-performance liquid chromatographic enantioseparation of unusual β-amino acids is reported. The investigated amino acids were saturated or unsaturated alicyclic β-3-homo-amino acids and bicyclic β-amino acids. Prior to chromatographic analyses, all amino acids were transformed to N-3,5-dinitrobenzoyl- or N-3,5-dimethylbenzoyl form to ensure a π-acidic or π-basic function and to enhance the π-acidic-π-basic interactions between analytes and chiral selectors. Chromatographic results are given as retention, separation and resolution factors. The chromatographic conditions were varied to achieve optimal separation. The sequence of elution of the enantiomers was determined in some cases.",
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AU - Forró, E.

AU - Fülöp, F.

AU - Armstrong, Daniel W.

AU - Péter, A.

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AB - The application of 3,5-dimethylphenyl-carbamoylated-β-cyclodextrin (Cyclobond I 2000 DMP) and 2,6-dinitro-4-trifluoromethylphenyl-ether-β-cyclodextrin-based (Cyclobond DNP) chiral stationary phases for the high-performance liquid chromatographic enantioseparation of unusual β-amino acids is reported. The investigated amino acids were saturated or unsaturated alicyclic β-3-homo-amino acids and bicyclic β-amino acids. Prior to chromatographic analyses, all amino acids were transformed to N-3,5-dinitrobenzoyl- or N-3,5-dimethylbenzoyl form to ensure a π-acidic or π-basic function and to enhance the π-acidic-π-basic interactions between analytes and chiral selectors. Chromatographic results are given as retention, separation and resolution factors. The chromatographic conditions were varied to achieve optimal separation. The sequence of elution of the enantiomers was determined in some cases.

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KW - Chiral stationary phases (CSPs)

KW - High-performance liquid chromatography (HPLC)

KW - Unusual β-3-homo amino acids

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