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Elucidation of the chromatographic enantiomer elution order for praziquantel: An experimental and theoretical assessment
Author(s) -
Silva Camilla Fonseca,
Nascimento Tienne Aparecida,
Guimarães Luciana,
Borges Keyller Bastos,
Nascimento Clebio Soares
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23164
Subject(s) - chemistry , enantiomer , elution , diastereomer , density functional theory , hydrogen bond , chromatography , stacking , high performance liquid chromatography , computational chemistry , organic chemistry , molecule
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.