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Related Experiment Videos

Probing polyvalency in artificial systems exhibiting molecular recognition.

David A Fulton1, Stuart J Cantrill, J Fraser Stoddart

  • 1Department of Chemistry and Biochemistry, University of California-Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA.

The Journal of Organic Chemistry
|November 9, 2002
PubMed
Summary
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Researchers studied polyvalency using crown ether clusters and dialkylammonium ligands. Clustering crown ethers hindered monovalent ligand binding but significantly enhanced polyvalent ligand complexation, increasing binding constants by approximately 100-fold.

Area of Science:

  • Supramolecular Chemistry
  • Host-Guest Chemistry
  • Organic Chemistry

Background:

  • Polyvalency, the interaction between multiple binding sites on receptors and ligands, is crucial in biological systems.
  • Understanding polyvalency in synthetic systems offers insights into molecular recognition and the design of novel materials.
  • Crown ethers are well-established hosts for cations, and their multivalent presentation is an area of active research.

Purpose of the Study:

  • To investigate the impact of clustering multiple crown ether units on receptor-ligand interactions.
  • To compare the binding affinities of monovalent and multivalent crown ether receptors with mono- and divalent ligands.
  • To quantify the polyvalent effect in synthetic host-guest systems.

Main Methods:

  • Synthesis of multivalent receptors: DB24C8 CLUSTER and BMP25C8 CLUSTER, featuring seven crown ether units on a beta-cyclodextrin core.

Related Experiment Videos

  • Preparation of complementary monovalent and divalent ligands containing dialkylammonium centers, functionalized with fluorine for NMR detection.
  • Binding studies using (19)F NMR spectroscopy to determine average binding constants (K(AVE)) for receptor-ligand complexation.

    • Main Results:

    • Clustering seven dibenzo[24]crown-8 (DB24C8) or benzometaphenylene[25]crown-8 (BMP25C8) moieties was detrimental to complexation with monovalent ligands compared to individual crown ethers.
    • The multivalent receptors (DB24C8 CLUSTER and BMP25C8 CLUSTER) exhibited significantly enhanced binding of divalent ligands.
    • Polyvalent binding constants (K(POLY)) for divalent ligands were approximately 2 orders of magnitude higher than component association constants (K(A)).

    Conclusions:

    • Multivalency can dramatically enhance binding affinity, even when the clustered host units show reduced affinity for monovalent guests.
    • The spatial arrangement and cooperativity in multivalent systems are critical factors in achieving high binding avidity.
    • This study provides a quantitative framework for understanding and designing polyvalent interactions in synthetic supramolecular chemistry.