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Molecules 2019, 24(6), 1021; https://doi.org/10.3390/molecules24061021

Molecular Simulation of the Separation of Isoleucine Enantiomers by β-Cyclodextrin

Departamento de Física, Universidad de La Laguna, 38202 La Laguna, Tenerife, Spain
Academic Editor: Bernard Martel
Received: 22 February 2019 / Revised: 11 March 2019 / Accepted: 11 March 2019 / Published: 14 March 2019
(This article belongs to the Special Issue Cyclodextrin Chemistry 2018)
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Abstract

Molecular mechanics and dynamics simulations were carried out to study the capacity of isoleucine enantiomers to form inclusion complexes with β–cyclodextrin, and to be discriminated by this chiral compound, in vacuo and with different solvents. Solvents were characterized not only by the value of dielectric constant ε in the Coulombic interaction energy, but also by the neutral and zwitterion configurations of isoleucine. Whereas the discrimination between the enantiomers for ε ≤ 2 is due to the electrostatic contribution, these differences are mainly due to the Lennard-Jones potential for ε > 2. The most enantioselective regions are located near the cavity walls, independently of the solvent. D-Ile is more stable than L-Ile in broader regions in vacuo, but L-Ile presents more stable locations with water. Isoleucine can form inclusion complexes with β–cyclodextrin in vacuo and with different solvents. Two probable configurations are deduced from the molecular dynamics simulation, in which the guest is always inside the cavity and with the carboxylic end of the amino acid oriented towards either rim of β–CD. In the simulation, the enantiomers preferentially occupy regions with greater chiral discrimination. The first eluted enantiomer in vacuo and with different solvents is L-Ile, independently of the solvent polarity. View Full-Text
Keywords: cyclodextrins; isoleucine; enantiomers; interaction energy; molecular mechanics; molecular dynamics; inclusion complex; elution order cyclodextrins; isoleucine; enantiomers; interaction energy; molecular mechanics; molecular dynamics; inclusion complex; elution order
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Alvira, E. Molecular Simulation of the Separation of Isoleucine Enantiomers by β-Cyclodextrin. Molecules 2019, 24, 1021.

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