Elucidation of the chromatographic enantiomer elution order for praziquantel: An experimental and theoretical assessment. Issue 3 (15th January 2020)

• Record Type: Journal Article
• Authors: Silva, Camilla Fonseca; do Nascimento, Tienne Aparecida; Guimarães, Luciana; Borges, Keyller Bastos; Nascimento, Clebio Soares
• Is Part Of: Chirality. Volume 32:Issue 3(2020)
• Page Start: 353
• Page End: 358
• Publication Date: 2020-01-15
• Subjects: cellulose‐Tris‐(3, 5‐dimethylphenylcarbamate) polysaccharide -- density functional theory -- enantiomeric elution order -- enantioselective separation -- high‐performance liquid chromatography -- theoretical calculations; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.23164
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: 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. Abstract :