Analytica chimica acta · 2026
A synergy strategy of deep eutectic solvents and boric acid modified β-CD polymer for enhancing enantioseparation in HPLC.
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Yuan Xiaoqian, Cheng Ziyi, Fu Jiajia, Duan Wanting, Cui Yuchen, Tang Ruijun, Wang Xinru, Li Youxin
Аннотация
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.
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.