Related Experiment Video
Updated: Aug 9, 2026
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
A synergy strategy of deep eutectic solvents and boric acid modified β-CD polymer for enhancing enantioseparation in
Xiaoqian Yuan1, Ziyi Cheng1, Jiajia Fu1
1Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, School of Pharmaceutical Science and Technology, Faculty of Medicine, Tianjin University, Tianjin, 300072, China.
Background:
Enantiomeric separation is essential in pharmaceutical analysis because enantiomers can differ markedly in pharmacological activity, metabolism, and safety. HPLC using chiral mobile-phase additives (CMPAs), particularly cyclodextrin-based selectors, provides a flexible and cost-effective alternative to dedicated chiral stationary phases. However, conventional cyclodextrin CMPA systems are often limited by insufficient stereodiscrimination under aqueous-organic mobile-phase conditions, where solvation and weak noncovalent interactions can restrict chiral recognition. This study explores the potential of deep eutectic solvents (DESs) as auxiliary mobile-phase modifiers for enhancing enantioseparation in β-cyclodextrin polymer-based HPLC chiral mobile phase analysis.
Results:
Seven DESs with different hydrogen-bond donor/acceptor compositions and molar ratios were prepared and characterized by FT-IR, 1H NMR, DSC, viscosity, and column-pressure measurements. The DESs were incorporated into HPLC-CMPA systems containing boric acid-modified β-cyclodextrin polymer (BA-β-CDP) and four other cyclodextrin derivatives as chiral selectors. The DES-assisted BA-β-CDP system improved the resolution of all ten chiral analytes. The resolutions of chlorpheniramine, propranolol, metoprolol, and bisoprolol increased by 17.16, 14.61, 12.63, and 8.86, respectively. Furthermore, danshensu, salbutamol, naringin and neohesperidin achieved complete separation with Rs of 2.60, 1.82, 1.52 and 2.52, respectively, which were slightly separated (Rs = 0.98 for danshensu and 0.40 for salbutamol) or remained unresolved in the absence of DES (Rs = 0 for naringin and neohesperidin). The system remained stable for at least 60 days, with RSD values below 1.30%.
Significance And Novelty:
In this paper, deep eutectic solvents (DESs) by modulating the hydrogen-bonding network and solvation microenvironment were introduced as auxiliary modifiers into the chiral mobile-phase additive (CMPA) mode of HPLC for the first time which could synergistically enhance chiral recognition. This strategy offers a green, versatile, and cost-effective solution for advancing chiral separation on conventional C18 columns in HPLC.
Related Concept Videos
01:05High-Performance Liquid Chromatography: Elution Process
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
01:11High-Performance Liquid Chromatography: Introduction
In HPLC, two phases play a critical role in the separation process:
01:30Capillary Electrophoresis: Applications
Capillary zone electrophoresis (CZE) separates ionic components based on their electrophoretic mobility. It has been used to separate proteins, amino acids,...
03:08Hydroboration-Oxidation of Alkenes
01:17Ion Exchange