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Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024

Copyright (c) 2024 Shiv Kumar Alwera

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Sensitive Detection and Enantioseparation of β-Blockers with Quinoline Based Active Chiral Reagents using HPLC: Separation Mechanism and DFT Modelling

https://doi.org/10.14233/ajchem.2024.31487
N.K. Sharma
Department of Chemistry, Government P.G. College, Bundi-323001, India
https://orcid.org/0000-0002-4098-8143
L. Kaur
Department of Nutrition and Dietetics, Manav Rachna International Institute of Research and Studies, Faridabad-121004, India
https://orcid.org/0000-0002-4634-7355
S. Alwera
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, India
https://orcid.org/0000-0002-5897-2166
V.S. Talismanov
Department of Chemistry, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, 141701, Russian Federation
https://orcid.org/0000-0003-0511-9943
A.K. Tripathi
Department of Chemistry, Deen Dayal Upadhyaya Gorakhpur University, Gorakhpur-273009, India
https://orcid.org/0000-0003-1210-9516
A. Mondal
Department of Chemistry, Brahmananda Keshab Chandra College, Kolkata-700108, India
https://orcid.org/0009-0003-7355-3036

Corresponding Author(s) : S. Alwera

ashiv.kumalwera@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024

Abstract

A sensitive and effective method for the detection and enantioseparation of β-blockers was developed. Three quinoline-based active chiral reagents were prepared followed by an amide and ester formation reaction. The synthesized active chiral reagents were characterized with spectroscopic techniques such as NMR, FT-IR, UV, HRMS and elemental analyzer. The active reagents were used in the diastereomerization of the racemic β-blockers (propranolol, metoprolol and carvedilol). Synthesized diastereomeric pairs were then subjected to RP-HPLC for chromatographic separation. The eluting phase, which consists of a buffer solution with acetonitrile, was used for analysis. The separation analysis results were optimized in the presence of variables such as eluting phase ratio, concentration and pH. Additionally, the separation process, elution order and stable conformer of diastereomers were studied by developing minimized energy structures of prepared diastereomeric pairs using DFT.

Keywords

Quinoline-8-carboxylic acid β-Blockers Diastereomerization Enantioseparation Active reagents RP-HPLC
Sharma, N., Kaur, L., Alwera, S., Talismanov, V., Tripathi, A., & Mondal, A. (2024). Sensitive Detection and Enantioseparation of β-Blockers with Quinoline Based Active Chiral Reagents using HPLC: Separation Mechanism and DFT Modelling. Asian Journal of Chemistry, 36(6), 1334–1340. https://doi.org/10.14233/ajchem.2024.31487
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