Chiral discrimination studies of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid by high-performance liquid chromatography and NMR spectroscopy

Wonjae Lee, Eunjung Bang, Chae Sun Baek, Weontae Lee

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Abstract

Chiral discrimination studies using (+)-(18-crown-6)-2,3,11,12- tetracarboxylic acid (18-C-6-TA) as a chiral selector were performed by high-performance liquid chromatography (HPLC) and NMR spectroscopy. The enantiomers of alanine (Ala) or alanine methyl ester (Ala-ME) were well separated on the chiral stationary phases (CSPs) derived from (+)-18-C-6-TA by HPLC. The chiral selector, (+)-18-C-6-TA, used in the CSP was also applied for the chiral discrimination of the Ala and Ala-ME enantiomers, and it discriminated these enantiomers successfully by NMR spectroscopy. The chemical shift differences (ΔΔδ) of the α-proton of these enantiomers in the presence of an equimolecular solution of 18-C-6-TA were observed to be 0.10 ppm for Ala in methanol-d4 containing 10 mM H2SO4 and 0.11 ppm for Ala-ME in methanol-d4. The observed NMR results agreed with the chromatographic data on the (+)-18-C-6-TA-derived CSP by HPLC in terms of both the elution order and solvents effects.

Original languageEnglish
Pages (from-to)389-395
Number of pages7
JournalMagnetic Resonance in Chemistry
Volume42
Issue number4
DOIs
Publication statusPublished - 2004 Apr 1

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Science(all)

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