Supercritical fluid chromatography in chiral separations: Evaluation of equivalency of polysaccharide stationary phases

Abstract

Nine different chiral columns based on covalently immobilized or coated tris(3,5‐dimethylphenylcarbamate) cellulose and amylose have been explored. We evaluated their respective enantioselective potential including the enantioseparation and qualitative characteristics of peaks. The generic screening conditions were using gradient elution from 5 to 40% organic modifier/CO2 during 3 min with about 40 enantiomer pairs. Primary screening was carried out using ten different mobile phases varying in type of additives while using one representative amylose‐ and one cellulose‐based column. The complete evaluation of all nine columns was then carried out using three best performing organic modifiers: (1) methanol + 0.1% trifluoroacetic acid + 0.1% diethylamine, (2) isopropanol + 0.1% trifluoroacetic acid + 0.1% diethylamine, and (3) methanol + 0.1% ammonium hydroxide. Equivalency of different columns with the same chiral selector was not confirmed. Columns with the same stationary phase but different supports or manufacturing methods displayed differences in enantioselectivity and general performance. The similarity corresponded to 62 and 63% for the three cellulose‐coated columns taking CEL1 as the reference. The similarity was 67% for the pair of amylose‐based coated columns. For immobilized columns, the similarity was 69 and 59% for celluloses and amyloses pairs, respectively. The best performing column based on success rate of enantioseparation was Chiralcel OD‐3 when using methanol + 0.1% trifluoroacetic acid and 0.1% diethylamine combined additive.

Direct enantioselective gradient reversed‐phase ultra‐high performance liquid chromatography tandem mass spectrometry method for 3‐hydroxy alkanoic acids in lipopeptides on an immobilized 1.6 μm amylose‐based chiral stationary phase

“…Polysaccharide-based chiral stationary phases (CSPs) appreciate tremendous popularity, which is mainly attributed to their wide range of versatility [16][17][18]. Traditionally theses phases were predominantly used in normal phase mode, but actually have multimodal applicability.…”

Enantioseparation and dissipation monitoring of oxathiapiprolin in grape using supercritical fluid chromatography tandem mass spectrometry

“…Compared with UHPLC, SFC has many advantages such as short analysis time, high resolution, as well as the low organic solvent consumption due to it combined the gas and liquid phases superior properties [19]. An environmental‐friendly mobile phase─carbon dioxide (CO 2 ) fluid own the nontoxic, nonreactive, low viscosity, and highly diffuse substance advantages, over the other widely used organic solvents, which greatly improved the separation efficiency and shortened the analysis time [20, 21]. MS is widely used in pesticides detection due to its high specificity and sensitivity.…”

Recent Advances in Chiral Analysis of Proteins and Peptides

“…The best performing column was a Chiralpak OD-3 with methanol + 0.1% trifluoroacetic acid and 0.1% diethylamine combined additive separation conditions. The combination of alcohol and alkylamine as a co-solvent and a mobile-phase additive seemed beneficial for enantioseparation [103]. Indeed, Lipka et al optimized their concentration (20-40% ethanol + 0.3-3.0% trimethylamine) according to the amino acid enantiomers to be separated using an immobilized cellulose-based CSP (i-Cellulose-5).…”