Unusually high enantioselectivity in high-performance liquid chromatography using cellulose tris(4-methylbenzoate) as a chiral stationary phase |
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Authors: | Roberto Cirilli Stefano Alcaro Rossella Fioravanti Daniela Secci Stefano Fiore Francesco La Torre Francesco Ortuso |
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Affiliation: | 1. Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, I-00161 Rome, Italy;2. Dipartimento di Scienze Farmacobiologiche, Laboratorio di Chimica Farmaceutica, Università degli Studi “Magna Græcia”, Campus Universitario “Salvatore Venuta”, Viale Europa, I-88100 Catanzaro, Italy;3. Università “La Sapienza”, Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Piazzale A. Moro 5, I-00185 Rome, Italy |
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Abstract: | The cellulose tris(4-methylbenzoate) chiral stationary phase (CSP) (commercially known as Chiralcel OJ-H) exhibited an extremely high enantioselectivity when used in the HPLC resolution of N-thiocarbamoyl-3-(4′-prenyloxy)-phenyl-5-phenyl-4,5-dihydro-(1H) pyrazole (Compound 1), in both normal-phase and polar organic conditions. Using n-hexane–ethanol (80:20, v/v) as a mobile phase, an enantioseparation factor value of 138.5 was found. In order to modulate the elution time of the longer retained enantiomer, a simple HPLC procedure was developed. The optimized analytical protocol was based on the stopped flow technique and did not involve any change in mobile phase composition. The stronger interaction energy of the (S) enantiomer compared to that of the (R) enantiomer was mainly attributed to the formation of a hydrogen bonding between the amino group of the thiocarbamoyl moiety and the carbonyl oxygen of the CSP. |
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Keywords: | Enantiomer separation Enantioselectivity Chiral stationary phase Chiralcel OJ-H Stopped-flow HPLC Temperature effects |
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