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Performance of the IEF-MST solvation continuum model in the SAMPL2 blind test prediction of hydration and tautomerization free energies

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Abstract

The IEF-MST continuum solvation model is used to predict the hydration free energies and tautomeric preferences of a set of multifunctional compounds compiled as a blind test for computational solvation methods in the SAMPL2 contest. Computations of hydration free energies was performed using both HF/6-31G(d) and B3LYP/6-31G(d) versions of the IEF-MST model. For tautomeric preferences, the IEF-MST data was combined with the gas phase free energy differences predicted at different levels of theory ranging from MP2/6-31+G(d) to MP2/CBS+[CCSD-MP2/6-31+G(d)] levels. Comparison with the experimental data provided for hydration free energies yields a root-mean square deviation (rmsd) close to 2.3 kcal/mol, which is quite remarkable, especially considering the reduced set of training compounds used in the parametrization of the IEF-MST method. With regard to tautomerism, the lowest error in the prediction of the relative stabilities between tautomers in solution is obtained by combining MP2/CBS+[CCSD-MP2/6-31+G(d)] results with IEF-MST hydration free energies, yielding a rmsd of ca. 3.4 kcal/mol. The results illustrate the delicate balance that must be kept between the intrinsic relative stabilities in the gas phase and the differential hydration preferences in order to obtain an accurate description of the prototropic tautomerism in bioorganic compounds.

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Acknowledgments

We acknowledge the financial support from the Ministerio de Innovación y Ciencia (MICINN; SAF2008-05595) and Generalitat de Catalunya (2009-SGR00298), and the computational facilities provided by the Centre de Supercomputació de Cataluyna (CESCA) and the Barcelona Supercomputing Center (BSC) are acknowledged.

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Authors and Affiliations

  1. Departament de Fisicoquímica and Institut de Biomedicina (IBUB), Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal 643, 08028, Barcelona, Spain

    Ignacio Soteras & F. Javier Luque

  2. Molecular Modeling and Bioinformatics Unit, Institut de Recerca Biomèdica, Barcelona Scientific Park, Josep Samitier 1-6, 08028, Barcelona, Spain

    Modesto Orozco

  3. Department of Life Sciences, Barcelona Supercomputing Centre, Jordi Girona 29, 08034, Barcelona, Spain

    Modesto Orozco

  4. Departament de Bioquímica, Facultat de Biologia, Universitat de Barcelona, Av. Diagonal 647, Barcelona, 08028, Spain

    Modesto Orozco

Authors
  1. Ignacio Soteras
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  2. Modesto Orozco
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  3. F. Javier Luque
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Corresponding author

Correspondence to F. Javier Luque.

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Soteras, I., Orozco, M. & Luque, F.J. Performance of the IEF-MST solvation continuum model in the SAMPL2 blind test prediction of hydration and tautomerization free energies. J Comput Aided Mol Des 24, 281–291 (2010). https://doi.org/10.1007/s10822-010-9331-y

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  • DOI: https://doi.org/10.1007/s10822-010-9331-y

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