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Novel chiral recognition elements for molecularly imprinted polymer preparation.

M Knutsson1, H S Andersson, I A Nicholls

  • 1Bioorganic Chemistry Laboratory, University of Kalmar, Sweden.

Journal of Molecular Recognition : JMR
|March 17, 1999
PubMed
Summary

A new chiral monomer system enhances molecular imprinting for stereoselective polymers. This system creates stronger binding sites and can even reverse inherent chiral selectivity, improving separation of isomers.

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Area of Science:

  • Chiral chemistry
  • Polymer science
  • Analytical chemistry

Background:

  • Molecular imprinting (MI) is a powerful technique for creating polymers with specific recognition sites.
  • Developing chiral selectors for enantioselective separations remains a significant challenge in analytical chemistry.
  • Chiral functional monomers are crucial for imparting stereospecificity in imprinted polymers.

Purpose of the Study:

  • To introduce a novel chiral functional monomer system for molecular imprinting.
  • To investigate the ability of this system to create polymers with enhanced ligand-binding capacities and stereoselectivity.
  • To evaluate the performance of the imprinted polymers in separating chiral molecules.

Main Methods:

  • Synthesis of a novel chiral monomer: dibenzyl (2R,3R)-O-monoacryloyl tartrate.

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  • Utilizing the monomer's hydroxyl group for directed template-monomer interactions during polymerization.
  • Deprotection of benzyl ester groups to yield carboxylate recognition sites.
  • Applying the molecular imprinting technique to cinchonidine alkaloids (+)-cinchonine and (-)-cinchonidine.

    • Main Results:

    • The developed monomer system successfully created molecularly imprinted polymers (MIPs).
    • The imprinted polymers exhibited stereoselective binding towards the target alkaloids.
    • Imprinting with (+)-cinchonine resulted in a polymer that reversed the inherent chiral selectivity of the monomer matrix.
    • The deprotection step enhanced the ligand-binding capacity of the recognition sites.

    Conclusions:

    • The novel chiral functional monomer system is effective for creating highly stereoselective MIPs.
    • This system offers a promising approach for enantioselective separation applications.
    • The ability to reverse inherent chiral selectivity opens new avenues in chiral recognition material design.