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

  • Karina Kapusta
  • Natalia Sizochenko
  • Sedat Karabulut
  • Sergiy Okovytyy
  • Eugene Voronkov
  • Jerzy Leszczynski
Original Paper
Part of the following topical collections:
  1. P. Politzer 80th Birthday Festschrift


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.


Amino acid QSPR Optical rotation Chirality NMR tensors Quantum chemical descriptors Molecular descriptors 



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).

Supplementary material

894_2018_3593_MOESM1_ESM.docx (112 kb)
ESM 1 (DOCX 112 kb)


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Interdisciplinary Center for Nanotoxicity, Department of Chemistry, Physics and Atmospheric SciencesJackson State UniversityJacksonUSA
  2. 2.Oles Honchar Dnipropetrovsk National UniversityDnipropetrovskUkraine

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