title: Exploring chiral separation of 3-carboxamido-5-aryl isoxazole derivatives by supercritical fluid chromatography on amylose and cellulose tris dimethyl- and chloromethyl phenylcarbamate polysaccharide based stationary phases.
abstract: Four polysaccharide based chiral stationary phases were chosen, two chlorinated: Lux™ Amylose-2 (tris-5-chloro-2-methylphenylcarbamate of amylose) and Lux™ Cellulose-2 (tris-3-chloro-4-methylphenylcarbamate of cellulose) and two methylated: Chiralpak®AD-H (tris-3,5-dimethylphenylcarbamate of amylose) and Chiralcel®OD-H (tris-3,5-dimethylphenylcarbamate of cellulose) to separate four 3-carboxamido-5-aryl isoxazole derivatives by supercritical fluid chromatography. The effect of chiral stationary phase, co-solvent nature (MeOH, EtOH, 2-PrOH and ACN) and percentage (10-20%), temperature (20-45°C) and chemical structure of the compounds on retention, resolution and elution order were thoroughly studied. In addition, thermodynamic parameters were determined from the linear portion of the Van't Hoff plots. For all the derivatives, the Lux™ Cellulose-2 and Chiralpak®AD-H provided excellent resolutions (Rs=9.78) in short run time (under 6min). The preparation of about 10mg of each of the eight enantiomers was achieved successfully on a Chiralpak®AD-H with various percentages of ethanol as a co-solvent. Lastly, the enantiomeric purity of each of the eight individual enantiomer generated was determined and found higher than 98%.
authors.affiliation: Univ. Lille, Inserm, U995-LIRIC-Lille Inflammation Research International Center, F-59000 Lille, France.
authors.forename: Yasmine
authors.initials: Y
authors.lastname: Zehani
authors.affiliation: Univ. Lille, Inserm, U995-LIRIC-Lille Inflammation Research International Center, F-59000 Lille, France.
authors.forename: Lucas
authors.initials: L
authors.lastname: Lemaire
authors.affiliation: Univ. Lille, Inserm, U995-LIRIC-Lille Inflammation Research International Center, F-59000 Lille, France.
authors.forename: Alina
authors.initials: A
authors.lastname: Ghinet
authors.affiliation: Univ. Lille, Inserm, U995-LIRIC-Lille Inflammation Research International Center, F-59000 Lille, France.
authors.forename: Régis
authors.initials: R
authors.lastname: Millet
authors.affiliation: Univ. Lille, Inserm, U995-LIRIC-Lille Inflammation Research International Center, F-59000 Lille, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Chavatte
authors.affiliation: EA GRITA 7365, Univ. Lille, Faculté de Pharmacie de Lille, F-59000 Lille, France.
authors.forename: Claude
authors.initials: C
authors.lastname: Vaccher
authors.affiliation: Univ. Lille, Inserm, U995-LIRIC-Lille Inflammation Research International Center, F-59000 Lille, France. Electronic address: emmanuelle.lipka@univ-lille2.fr.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Lipka
mesh_terms: D000688:Amylose / Q000737:chemistry*; D002482:Cellulose / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D025924:Chromatography, Supercritical Fluid; D007555:Isoxazoles / Q000737:chemistry*; D010755:Organophosphates / Q000737:chemistry*; D048448:Phenylcarbamates / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D015203:Reproducibility of Results; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
chemical_list: C504080:3,5-dimethylphenylcarbamate; D007555:Isoxazoles; D010755:Organophosphates; D048448:Phenylcarbamates; D011134:Polysaccharides; D012997:Solvents; C012085:tris(2,3-dibromopropyl)phosphate; D002482:Cellulose; D000688:Amylose
keywords: Amylose and cellulose (tris-3,5-dimethylphenylcarbamate); Lux amylose (tris-5-chloro-2-methylphenylcarbamate); Lux cellulose (tris-3-chloro-4-methylphenylcarbamate); Small-scale preparative separation; Thermodynamic study