Elucidation of the chromatographic enantiomer elution order for praziquantel: An experimental and theoretical assessment.

Autor: Silva CF; Departamento de Ciências Naturais (DCNAT), Universidade Federal de São João Del-Rei (UFSJ), Campus Dom Bosco, São João, Minas Gerais, Brazil., do Nascimento TA; Departamento de Ciências Naturais (DCNAT), Universidade Federal de São João Del-Rei (UFSJ), Campus Dom Bosco, São João, Minas Gerais, Brazil., Guimarães L; Departamento de Ciências Naturais (DCNAT), Universidade Federal de São João Del-Rei (UFSJ), Campus Dom Bosco, São João, Minas Gerais, Brazil., Borges KB; Departamento de Ciências Naturais (DCNAT), Universidade Federal de São João Del-Rei (UFSJ), Campus Dom Bosco, São João, Minas Gerais, Brazil., Nascimento CS Jr; Departamento de Ciências Naturais (DCNAT), Universidade Federal de São João Del-Rei (UFSJ), Campus Dom Bosco, São João, Minas Gerais, Brazil.
Jazyk: angličtina
Zdroj: Chirality [Chirality] 2020 Mar; Vol. 32 (3), pp. 353-358. Date of Electronic Publication: 2020 Jan 15.
DOI: 10.1002/chir.23164
Abstrakt: In this work, we have studied both experimentally and theoretically the praziquantel (PZQ) chiral discrimination. According to the main results, the enantioseparation of PZQ was efficiently optimized by HPLC on the reverse phase from the Chiralpak IB column, which has cellulose tris (3,5-dimethylphenylcarbamate) (CDMPC) as a chiral selector. The thermodynamic and structural parameters obtained via density functional theory (DFT) calculations pointed out the chiral discrimination as well as the enantiomeric elution order of PZQ, thus elucidating the experimental data and validating our proposed method. Finally, the hydrogen bonds and π-π stacking interactions played a key role in the discrimination between the PZQ diastereomeric complexes formed.
(© 2020 Wiley Periodicals, Inc.)
Databáze: MEDLINE
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