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Chiral separation using molecularly imprinted heteroaromatic polymers

M Kempe1, L Fischer, K Mosbach

  • 1University of Lund, Sweden.

Journal of Molecular Recognition : JMR
|March 1, 1993
PubMed
Summary
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Novel polymers were created for enantioselective recognition of amino acids using HPLC. Polymers with 4-vinylpyridine showed better racemic resolution than those with 1-vinylimidazole, demonstrating selective molecular recognition.

Area of Science:

  • Polymer Chemistry
  • Analytical Chemistry
  • Chiral Separations

Background:

  • Molecular imprinting is a powerful technique for creating synthetic receptors.
  • Enantioselective recognition of chiral molecules is crucial in pharmaceuticals and biochemistry.
  • High-performance liquid chromatography (HPLC) is a standard method for separating complex mixtures.

Purpose of the Study:

  • To develop novel molecularly imprinted polymer (MIP) systems for the enantioselective recognition of carboxylic and N-protected amino acids.
  • To investigate the efficiency of MIPs as stationary phases in HPLC for chiral separations.
  • To compare the performance of polymers functionalized with 4-vinylpyridine versus 1-vinylimidazole.

Main Methods:

  • Synthesis of molecularly imprinted polymers using 4-vinylpyridine and 1-vinylimidazole as functional monomers.

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  • Utilizing non-covalent interactions for the formation of recognition sites within the polymer matrix.
  • Employing the developed polymers as stationary phases in HPLC for the separation of enantiomers.
  • Determining the optimal molar ratio of functional monomer to template molecule for effective imprinting.

    • Main Results:

    • Polymers prepared with 4-vinylpyridine exhibited higher efficiency in racemic resolution compared to those with 1-vinylimidazole.
    • The MIPs demonstrated the highest affinity for the specific enantiomer used as the template during polymerization.
    • Imprinted polymers created using a racemic template molecule did not show enantioselectivity.
    • An optimal molar ratio of 12:1 for 4-vinylpyridine to Cbz-L-Asp-OH was identified for effective imprinting.
    • The polymers displayed 'ligand selectivity,' successfully separating Cbz-D,L-Asp-OH but not Cbz-D,L-Glu-OH.

    Conclusions:

    • Novel MIP systems based on 4-vinylpyridine and 1-vinylimidazole are effective for enantioselective recognition of amino acids.
    • 4-Vinylpyridine-based polymers offer superior performance in chiral separations via HPLC compared to 1-vinylimidazole-based polymers.
    • The study highlights the potential of tailored MIPs for selective separation of structurally similar chiral compounds.