Enantioselective potential of polysaccharide‐based chiral stationary phases in supercritical fluid chromatography

Abstract

The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5 μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO , respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

“…The 3,5‐dimethylphenyl carbamate side chains surround the helical grooves and delimit the chiral environments. Naturally and chemically modified amylose have highly rigid and well‐hydrophobic cavity which can serve as a molecular acceptor to recognize a variety of organics, inorganics, biomolecule‐forming host guests as well as supramolecular complexes . Figure shows the molecular chemical structure of CSP which was purchased from Daicel Chiral Technologies (Shanghai) Co. Ltd.…”

Enantioselective separation of (±)‐β‐hydroxy‐1,2,3‐triazoles by supercritical fluid chromatography and high‐performance liquid chromatography

“…High‐performance liquid chromatography (HPLC) is the major separation technique used for the qualitative and quantitative analysis of chiral compounds . The widespread use of HPLC may be attributed to advances on the development of chiral stationary phases (CSPs), which improved the separation of racemic compounds .…”

“…High-performance liquid chromatography (HPLC) is the major separation technique used for the qualitative and quantitative analysis of chiral compounds. 1,2 The widespread use of HPLC may be attributed to advances on the development of chiral stationary phases (CSPs), which improved the separation of racemic compounds. 3,4 Nevertheless, several limitations may be disadvantageous to the development of chiral methods by HPLC, such as long equi-libration time and long analysis time and the use of toxic and flammable solvents.…”

“…8,9 The polysaccharides-based derivatives (e.g., cellulose and amylose) CSPs are extensively used for HPLC as well as SFC enantioseparations due to versatility, durability, and sample loadability. 1,10 Comparative studies of enantioselective separations have been showed that both SFC and HPLC provide good selectivity; however, the advantage of SFC over HPLC occurs in terms of flow rate, resolution, time of analysis, consumption of solvent, and high throughput. 1,8,9,11 Thus, the SFC has been used not only for purification purpose, but also for method development and screening of chiral and achiral compounds in different matrices.…”

“…1,10 Comparative studies of enantioselective separations have been showed that both SFC and HPLC provide good selectivity; however, the advantage of SFC over HPLC occurs in terms of flow rate, resolution, time of analysis, consumption of solvent, and high throughput. 1,8,9,11 Thus, the SFC has been used not only for purification purpose, but also for method development and screening of chiral and achiral compounds in different matrices. 12,13 Therefore, in this work these two techniques were employed for the chiral separation of β-hydroxy-1,2,3triazoles, 14 which are an important class of heterocyclic compounds obtained only by synthetic methodologies.…”