title: Enantioseparation of pyroglutamide derivatives on polysaccharide based chiral stationary phases by high-performance liquid chromatography and supercritical fluid chromatography: a comparative study.
abstract: Analytical enantioseparation of three pyroglutamide derivatives with pharmacological activity against the purinergic receptor P2X7, was run in both high-performance liquid chromatography and supercritical fluid chromatography. Four polysaccharide based chiral stationary phases, namely amylose and cellulose tris (3,5-dimethylphenylcarbamate), amylose tris ((S)-α-methylbenzylcarbamate) and cellulose tris (4-methylbenzoate) with various mobile phases consisted of either heptane/alcohol (ethanol and 2-propanol) or carbon dioxide/alcohol (methanol or ethanol) mixtures, were investigated. After analytical screenings, the best conditions were transposed, for compound 1, to semi-preparative scale. Each approach was fully validated to meet the International Conference on Harmonisation requirements and compared. Whereas the limits of detection and quantification were near six-fold better in HPLC than in SFC (respectively 0.20 and 0.66 μM versus 1.11 and 3.53 μM for one of the enantiomers), in terms of low solvent consumption (7.2 mL of EtOH versus 3.2 mL of EtOH plus 28.8 mL of toxic and inflammable heptane per injection in SFC and HPLC, respectively), time effective cost (9 min versus 40 min per injection in SFC and HPLC, respectively) and yields (98% versus 71% in SFC and HPLC, respectively), the latter method proved its ecological superiority.
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France; Univ Lille Nord de France, UDSL, EA 4481, Hautes Etudes Ingénieur, F-59000 Lille, France.
authors.forename: Davy
authors.initials: D
authors.lastname: Baudelet
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France.
authors.forename: Nadège
authors.initials: N
authors.lastname: Schifano-Faux
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, Hautes Etudes Ingénieur, F-59000 Lille, France; University of Iasi, Department of Organic Chemistry, 'Al. I. Cuza' Faculty of Chemistry, 700506 Iasi, Romania.
authors.forename: Alina
authors.initials: A
authors.lastname: Ghinet
authors.affiliation: Univ Lille Nord de France, UDSL, Plateforme de binding, ICPAL, F-59000 Lille, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Dezitter
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France; Univ Lille Nord de France, UDSL, Plateforme de binding, ICPAL, F-59000 Lille, France.
authors.forename: Florent
authors.initials: F
authors.lastname: Barbotin
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, Hautes Etudes Ingénieur, F-59000 Lille, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Gautret
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, Hautes Etudes Ingénieur, F-59000 Lille, France.
authors.forename: Benoit
authors.initials: B
authors.lastname: Rigo
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Chavatte
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France.
authors.forename: Régis
authors.initials: R
authors.lastname: Millet
authors.affiliation: Univ Lille Nord de France, UDSL, Plateforme de binding, ICPAL, F-59000 Lille, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Furman
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France.
authors.forename: Claude
authors.initials: C
authors.lastname: Vaccher
authors.affiliation: Univ Lille Nord de France, UDSL, EA 4481, UFR Pharmacie, F-59000 Lille, France. Electronic address: emmanuelle.lipka@univ-lille2.fr.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Lipka
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D011134:Polysaccharides / Q000737:chemistry; D011761:Pyrrolidonecarboxylic Acid; D058486:Receptors, Purinergic P2X7; D013237:Stereoisomerism
chemical_list: D011134:Polysaccharides; D058486:Receptors, Purinergic P2X7; D011761:Pyrrolidonecarboxylic Acid
keywords: Amylose tris ((S)-1-phenylethylcarbamate); Chiral separation; Method validation; Semi-preparative chromatography; Supercritical fluid chromatography