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Enantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C 1 symmetry: experimental and theoretical approaches

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Abstract

The work involves an experimental (1H NMR) and theoretical (MD, MM-PBSA and DFT) investigation of the molecular recognition and discrimination properties of a chiral aza-15-crown-5 against methyl esters of alanine, phenylalanine and valine hydrochloride salts. The results indicate that the receptor binds enantiomers with moderate binding constants (88–1,389 M−1), with phenylalanine being more discriminated. The difference in experimental binding free energies (ΔG R − ΔG S) for alanine, phenylalanine and valine enantiomers were calculated as −0.36, −1.58 and 0.80 kcal mol−1, respectively. The differences in theoretical binding energies were calculated by MM-PBSA (ΔE R PB − ΔE S PB=) as −0.30, −1.45 and 0.88, by B3LYP/6-31+G(d) as −1.17, −0.84 and 0.74 and by M06-2X/6-31+G(d) as −1.40, −3.26 and 1.66 kcal mol−1. The data obtained give valuable information regarding the molecular recognition mode of the organoammonium complexes of chiral aza-crown ether with C 1 symmetry, which may be relevant to biological systems.

Left Superimposed lowest energy conformers of complexes of chiral aza-crown ether with the enantiomers of phenylalanine obtained from cluster analysis of MD trajectories. Right Non-linear dependence of 1H NMR chemical shifts of methyl groups of isopropyl in receptor 5 on the concentration of the enantiomers of valine ester salts

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Acknowledgments

We are grateful to Dicle University Research Council for financial support (DUAPK-02-FF-20, DUBAP-05-FF-31 and DUBAP-05-FF-32), Dr. Selami Ercan for Gaussian 09 facilities, The Scientific and Technological Research Council of Turkey (TÜBİTAK) for TR-GRID facilities and Professor D. Case for a waiver license of AMBER.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Dicle, Diyarbakir, 21280, Turkey

    Safak Özhan Kocakaya, Yılmaz Turgut & Necmettin Pirinççioglu

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  1. Safak Özhan Kocakaya
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  2. Yılmaz Turgut
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  3. Necmettin Pirinççioglu
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Correspondence to Necmettin Pirinççioglu.

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Kocakaya, S.Ö., Turgut, Y. & Pirinççioglu, N. Enantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C 1 symmetry: experimental and theoretical approaches. J Mol Model 21, 55 (2015). https://doi.org/10.1007/s00894-015-2604-6

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