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Binding of cyclic carboxylates to octa-acid deep-cavity cavitand

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Abstract

As part of the fourth statistical assessment of modeling of proteins and ligands (sampl.eyesopen.com) prediction challenge, the strength of association of nine guests (1–9) binding to octa-acid host was determined by a combination of 1H NMR and isothermal titration calorimetry. Association constants in sodium tetraborate buffered (pH 9.2) aqueous solution ranged from 5.39 × 102 M−1 in the case of benzoate 1, up to 3.82 × 105 M−1 for trans-4-methylcyclohexanoate 7. Overall, the free energy difference between the free energies of complexation of these weakest and strongest binding guests was ΔΔG° = 3.88 kcal mol−1. Based on a multitude of previous studies, the anticipated order of strength of binding was close to that which was actually obtained. However, the binding of guest 3 (4-ethylbenzoate) was considerably stronger than initially estimated.

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Acknowledgments

The authors acknowledge the financial support of the National Institutes of Health (GM098141) in carrying out this research.

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Authors and Affiliations

  1. Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA

    Corinne L. D. Gibb & Bruce C. Gibb

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  1. Corinne L. D. Gibb
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  2. Bruce C. Gibb
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Correspondence to Bruce C. Gibb.

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Gibb, C.L.D., Gibb, B.C. Binding of cyclic carboxylates to octa-acid deep-cavity cavitand. J Comput Aided Mol Des 28, 319–325 (2014). https://doi.org/10.1007/s10822-013-9690-2

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  • DOI: https://doi.org/10.1007/s10822-013-9690-2

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