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Molecules
Volume 23
Issue 2
10.3390/molecules23020443
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Article

Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach

by
Satoko Hayashi
*,
Yutaka Tsubomoto
and
Waro Nakanishi
*
Faculty of Systems Engineering, Wakayama University, 930 Sakaedani, Wakayama 640-8510, Japan
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(2), 443; https://doi.org/10.3390/molecules23020443
Received: 30 January 2018 / Revised: 10 February 2018 / Accepted: 14 February 2018 / Published: 17 February 2018
(This article belongs to the Section Computational and Theoretical Chemistry)
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Abstract

The nature of the E–E’ bonds (E, E’ = S and Se) in glutathione disulfide (1) and derivatives 2–3, respectively, was elucidated by applying quantum theory of atoms-in-molecules (QTAIM) dual functional analysis (QTAIM-DFA), to clarify the basic contribution of E–E’ in the biological redox process, such as the glutathione peroxidase process. Five most stable conformers a–e were obtained, after applying the Monte-Carlo method then structural optimizations. In QTAIM-DFA, total electron energy densities Hb(rc) are plotted versus Hb(rc) − Vb(rc)/2 at bond critical points (BCPs), where Vb(rc) are potential energy densities at BCPs. Data from the fully optimized structures correspond to the static nature. Those containing perturbed structures around the fully optimized one in the plot represent the dynamic nature of interactions. The behavior of E–E’ was examined carefully. Whereas E–E’ in 1a–3e were all predicted to have the weak covalent nature of the shared shell interactions, two different types of S–S were detected in 1, depending on the conformational properties. Contributions from the intramolecular non-covalent interactions to stabilize the conformers were evaluated. An inverse relationship was observed between the stability of a conformer and the strength of E–E’ in the conformer, of which reason was discussed. View Full-Text
Keywords: ab initio calculations; quantum theory of atoms-in-molecules (QTAIM); glutathione dichalcogenides; Monte-Carlo method ab initio calculations; quantum theory of atoms-in-molecules (QTAIM); glutathione dichalcogenides; Monte-Carlo method
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MDPI and ACS Style

Hayashi, S.; Tsubomoto, Y.; Nakanishi, W. Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach. Molecules 2018, 23, 443. https://doi.org/10.3390/molecules23020443

AMA Style

Hayashi S, Tsubomoto Y, Nakanishi W. Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach. Molecules. 2018; 23(2):443. https://doi.org/10.3390/molecules23020443

Chicago/Turabian Style

Hayashi, Satoko, Yutaka Tsubomoto, and Waro Nakanishi. 2018. "Behavior of the E–E’ Bonds (E, E’ = S and Se) in Glutathione Disulfide and Derivatives Elucidated by Quantum Chemical Calculations with the Quantum Theory of Atoms-in-Molecules Approach" Molecules 23, no. 2: 443. https://doi.org/10.3390/molecules23020443

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