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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MDPI AG
2022-06-01
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| author | Mladenka Jurin Darko Kontrec Tonko Dražić Marin Roje |
| author_facet | Mladenka Jurin Darko Kontrec Tonko Dražić Marin Roje |
| author_sort | Mladenka Jurin |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T13:02:20Z |
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| id | doaj.art-fec6a203ebf14512acdafd1bbbdc3e58 |
| institution | Directory Open Access Journal |
| issn | 2297-8739 |
| language | English |
| last_indexed | 2024-03-09T13:02:20Z |
| publishDate | 2022-06-01 |
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| series | Separations |
| spelling | doaj.art-fec6a203ebf14512acdafd1bbbdc3e582023-11-30T21:53:02ZengMDPI AGSeparations2297-87392022-06-019715710.3390/separations9070157Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary PhasesMladenka Jurin0Darko Kontrec1Tonko Dražić2Marin Roje3Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaDepartment of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaDepartment of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaDepartment of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaThe 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.https://www.mdpi.com/2297-8739/9/7/1573,5-disubstituted hydantoinsHPLCSFCenantioseparationimmobilized polysaccharide-based chiral stationary phasesDMC |
| spellingShingle | Mladenka Jurin Darko Kontrec Tonko Dražić Marin Roje Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases Separations 3,5-disubstituted hydantoins HPLC SFC enantioseparation immobilized polysaccharide-based chiral stationary phases DMC |
| title | Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases |
| title_full | Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases |
| title_fullStr | Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases |
| title_full_unstemmed | Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases |
| title_short | Enantioseparation of <i>syn</i>- and <i>anti</i>-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases |
| title_sort | enantioseparation of i syn i and i anti i 3 5 disubstituted hydantoins by hplc and sfc on immobilized polysaccharides based chiral stationary phases |
| topic | 3,5-disubstituted hydantoins HPLC SFC enantioseparation immobilized polysaccharide-based chiral stationary phases DMC |
| url | https://www.mdpi.com/2297-8739/9/7/157 |
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