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QSPR modeling of optical rotation of amino acids using specific quantum chemical descriptors

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Abstract

Many chemical phenomena occur in solution. Different solvents can change the optical activity of chiral molecules. The optical rotation angles of solutes of 75 amino acids in dimethylformamide, water and methanol were analyzed using the quantitative structure–activity relationships approach. For an accurate description of chirality, we used specific quantum chemical descriptors, which reflect the properties of a chiral center, and continuous symmetry measures. The set of specific quantum chemical descriptors for atoms located near the chiral center, such as Mulliken charges, the sum of Mulliken charges on an atom (with the hydrogen charges summed up with the adjacent non-hydrogen atoms), and nuclear magnetic resoncance tensors was applied. To represent solvent effects, we used mixture-like structural simplex descriptors and quantum chemical descriptors obtained for structures optimized for specified solvent using PBE1PBE/6-31G** level of theory with the polarizable continuum model. Multiple linear regression, M5P, and locally weighted learning techniques were used to achieve accurate predictions. The specific quantum chemical descriptors proposed here demonstrated high specificity in the majority of the developed models and established direct quantitative structure–property relationships.

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Acknowledgments

The authors gratefully acknowledge the funding of this research by the Ministry of Education and Science of Ukraine (Project #0116U001520), National Science Foundation (NSF/CREST HRD-1547754) and PREM (DMR-1205194) grants. This work also used the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by the National Science Foundation (grant #ACI-1053575).

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Authors and Affiliations

  1. Interdisciplinary Center for Nanotoxicity, Department of Chemistry, Physics and Atmospheric Sciences, Jackson State University, PO Box 17910, Jackson, MS, 39217-0510, USA

    Karina Kapusta, Natalia Sizochenko, Sedat Karabulut, Sergiy Okovytyy & Jerzy Leszczynski

  2. Oles Honchar Dnipropetrovsk National University, 72 Gagarin Ave., Dnipropetrovsk, 49010, Ukraine

    Karina Kapusta, Sergiy Okovytyy & Eugene Voronkov

Authors
  1. Karina Kapusta
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  2. Natalia Sizochenko
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  3. Sedat Karabulut
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  4. Sergiy Okovytyy
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  5. Eugene Voronkov
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  6. Jerzy Leszczynski
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Corresponding authors

Correspondence to Karina Kapusta or Jerzy Leszczynski.

Additional information

This paper is dedicated to Peter Politzer as a recognition of his outstanding contributions to the field of quantum and computational chemistry on the occasion of his 80th birthday.

This paper belongs to Topical Collection P. Politzer 80th Birthday Festschrift.

Eugene Voronkov is an independent researcher.

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Kapusta, K., Sizochenko, N., Karabulut, S. et al. QSPR modeling of optical rotation of amino acids using specific quantum chemical descriptors. J Mol Model 24, 59 (2018). https://doi.org/10.1007/s00894-018-3593-z

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  • DOI: https://doi.org/10.1007/s00894-018-3593-z

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