Innovative Chiral Column Boosts Enantioselective HPLC Separations

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In a recent study, a novel chiral column, based on a CC19-R porous organic cage, promises to enhance enantioselective HPLC separations.

In a recent study, researchers demonstrated that a novel chiral stationary phase (CSP) could improve enantioselective high-performance liquid chromatography (HPLC). The research team successfully synthesized this new CSP by covalently bonding a [4+6]-type homochiral porous organic cage (POC), known as CC19-R to thiolated silica, utilizing a thiol-ene click reaction. The researchers’ efforts were published in the Journal of Chromatography A (1).

A macro shot of a chromatography pump, revealing the inner workings and mechanical components used for precise fluid movement | Image Credit: © aicandy - stock.adobe.com

A macro shot of a chromatography pump, revealing the inner workings and mechanical components used for precise fluid movement | Image Credit: © aicandy - stock.adobe.com

CC19-R, which was synthesized through a Schiff-base reaction between 2-hydroxybenzene-1,3,5-tricarbaldehyde and (1R, 2R)-(-)-1,2-diaminocyclohexane, demonstrated enantioseparation capabilities (1). The CSP based on CC19-R was evaluated in both reversed phase HPLC (RP-HPLC) and normal phase HPLC (NP-HPLC) and successfully separated a diverse range of chiral compounds and pharmaceuticals, including alcohols, organic acids, ketones, diols, esters, and amines (1).

The team achieved the enantioseparation of 15 racemates in NP-HPLC and eleven racemates in RP-HPLC. Notably, several racemates, including 4-chlorobenzhydrol, cetirizine (in the form of dihydrochloride), 1,2-diphenyl-1,2-ethanediol, and 3-(benzyloxy)propane-1,2-diol, achieved exceptional resolution values of 3.66, 4.23, 6.50, and 3.50, respectively (1).

The new CSP exhibited improvements, successfully separating eight racemates in NP-HPLC and five racemates in RP-HPLC that were challenging on the NC1-R column. This revelation highlights the enhanced enantioselectivity and the significantly expanded separable range of chiral POC-type columns made possible by the CC19-R column (1).

Furthermore, the research team compared the performance of the CC19-R column with two commercial columns: Chiralpak AD-H (CSP: Amylose tris(3,5-dimethylphenylcarbamate)) and Chiralcel OD-H (CSP: Cellulose tris(3,5-dimethylphenylcarbamate)) (1). The CC19-R column was able to successfully separating racemates that the other columns struggled with.

The study also highlighted the stability and reproducibility of the CC19-R column. Even after undergoing multiple injections (100, 200, 300, and 400 times), the column demonstrated consistent performance, with a relative standard deviation (n = 5) for the retention time and resolution of less than 1.0% and 1.8%, respectively.

The research presents a pioneering approach in the world of chiral separations. The newly developed POC-based CSP, fabricated using CC19-R, demonstrated enantioseparation capabilities across a wide spectrum of compounds, outperforming both previous POC-based columns and commercial alternatives. With its potential for excellent resolution and straightforward synthesis methods, this CSP opens exciting prospects for chiral POC applications in HPLC racemic separation (1).

This article was written with the help of artificial intelligence and has been edited to ensure accuracy and clarity. You can read more about our policy for using AI here.

Reference

(1) Liang, R.-X.; Zhang, Y.-P.; Zhang, J.-H.; Gong, Y.-N.; Huang, B.; Wang, B.-J.; Xie, S.-M.; Yuan, L.-M. Engineering thiol-ene click chemistry for the preparation of a chiral stationary phase based on a [4+6]-type homochiral porous organic cage for enantiomeric separation in normal-phase and reversed-phase high performance liquid chromatography. J. Chromatogr. A. 2023, 1711, 464444. DOI: 10.1016/j.chroma.2023.464444

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