Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases

The enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-disubstituted hydantoins <b>5a</b>–<b>i</b> was investigated on three immobilized polysaccharide-based columns (CHIRAL ART Amylose-SA, CHIRAL ART Cellulose-SB, CHIRAL ART Cellulose-SC) by high pe...

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Bibliographic Details
Main Authors: Mladenka Jurin, Darko Kontrec, Tonko Dražić, Marin Roje
Format: Article
Language:English
Published: MDPI AG 2022-06-01
Series:Separations
Subjects:
Online Access:https://www.mdpi.com/2297-8739/9/7/157
Description
Summary:The enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-disubstituted hydantoins <b>5a</b>–<b>i</b> was investigated on three immobilized polysaccharide-based columns (CHIRAL ART Amylose-SA, CHIRAL ART Cellulose-SB, CHIRAL ART Cellulose-SC) by high performance liquid chromatography (HPLC) using <i>n</i>-hexane/2-PrOH (90/10, <i>v</i>/<i>v</i>) or 100% dimethyl carbonate (DMC) as mobile phases, respectively, and by supercritical fluid chromatography (SFC) using CO<sub>2</sub>/alcohol (MeOH, EtOH, 2-PrOH; 80/20, <i>v</i>/<i>v</i>) as a mobile phase. The chromatographic parameters, such as separation and resolution factors, have indicated that Amylose-SA is more suitable for enantioseparation of the most analyzed <i>syn</i>- and <i>anti</i>-3,5-disubstituted hydantoins than Celullose-SB and Cellulose-SC in both HPLC and SFC modalities. All three tested columns showed better enantiorecognition ability toward <i>anti</i>-hydantoins compared to <i>syn</i>-hydantoins, both in HPLC and SFC modes. We have demonstrated that environmentally friendly solvent DMC can be efficiently used as the mobile phase in HPLC mode for enantioseparation of hydantoins on the immobilized polysaccharide-based chiral stationary phases.
ISSN:2297-8739