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The Effect of the Stationary Phase on Resolution in the HPLC-Based Separation of Racemic Mixtures Using Vancomycin as a Chiral Selector: A Case Study with Profen Nonsteroidal Anti-Inflammatory Drugs

Lookup NU author(s): Dr Jie ZhangORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

© 2023 by the authors.Chiral resolution is a technique of choice, making it possible to obtain asymmetric and enantiomerically pure compounds from a racemic mixture. This study investigated the behavior of vancomycin when used as a chiral additive in high-performance liquid chromatography (HPLC) to separate enantiomers of nonsteroidal anti-inflammatory drugs (NSAIDs), including ketoprofen, ibuprofen, flurbiprofen, and naproxen enantiomeric impurities. We compared two achiral stationary phases (C18 and NH2) to assess the impact of mobile phase composition and stationary phase on the vancomycin retention time in the racemic resolution of drug enantiomers. Our results demonstrated the successful enantioseparation of all drugs using vancomycin in the mobile phase (phosphate buffer 0.05 M/2-propanol, 50/50) with an NH2 column. This enhanced separation on the NH2 column resulted from the chromatography system’s efficiency and vancomycin dimers’ stereoselective interaction on the NH2 surface. This study underscores the importance of stationary phase selection in the chiral resolution of NSAIDs with vancomycin as a chiral additive. It offers valuable insights for future research and development of NSAID chiral separation methods, highlighting potential vancomycin applications in this context.

Publication metadata

Author(s): Gherdaoui D, Yahoum MM, Toumi S, Tahraoui H, Bouazza F, Lefnaoui S, Zeghdaoui A, Amrane A, Jaouadi B, Zhang J

Publication type: Article

Publication status: Published

Journal: Symmetry

Year: 2023

Volume: 15

Issue: 12

Online publication date: 04/12/2023

Acceptance date: 27/11/2023

Date deposited: 08/01/2024

ISSN (electronic): 2073-8994

Publisher: Multidisciplinary Digital Publishing Institute (MDPI)

URL: https://doi.org/10.3390/sym15122154

DOI: 10.3390/sym15122154

Data Access Statement: The data presented in this study are available in the manuscript

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