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Chiral recognition of aromatic compounds by β-cyclodextrin based on bimodal complexation

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Abstract

The chiral recognition of the selected aromatic chiral compounds by native β-cyclodextrin (β-CD) based on bimodal complexation was studied using a flexible docking algorithm FDOCK. A quantitative empirical free energy relationship model was employed to predict the complex stability constants and the preferred binding modes. The results showed that the calculated complex stability constants are in good agreement with the experimental data. Furthermore, the main force responsible for host-guest complexation is the van der Waals force and the chiral molecules are completely included into the β-CD cavity. The chiral recognition for the selected aromatic chiral compounds is the result of the van der Waals force counterbalancing with the other effects, such as the electrostatic interaction and the hydrophobic effect.

Figure The favorable structures for the inclusion complexes of (S)_phenylbutyric with β-CD. View in the plane normal to the Z-axis. β-CD is shown in surface and (S)_phenylbutyric in CPK representation.

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Acknowledgements

This study is supported by the Natural Science Foundation of China (No. 20172048) and the Teaching and Research Award Program for Outstanding Young Professors (TRAPOYP) in Higher Education Institute, MOE, P.R.C. The construction and optimization of the structures used in this study by Insight II were completed in the laboratory of UMR 7565 CNRS/UHP, Université H. Poincaré, France.

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  1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, People’s Republic of China

    Wensheng Cai, Yanmin Yu & Xueguang Shao

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  1. Wensheng Cai
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  2. Yanmin Yu
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  3. Xueguang Shao
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Correspondence to Wensheng Cai.

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Cai, W., Yu, Y. & Shao, X. Chiral recognition of aromatic compounds by β-cyclodextrin based on bimodal complexation. J Mol Model 11, 186–193 (2005). https://doi.org/10.1007/s00894-004-0233-6

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  • DOI: https://doi.org/10.1007/s00894-004-0233-6

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