title: Enantioselective separation of chiral arylcarboxylic acids on an immobilized human serum albumin chiral stationary phase.
abstract: A series of 12 chiral arylcarboxylic acids were chromatographed on an immobilized human serum albumin chiral stationary phase (HSA-CSP). The effects of solute structure on chromatographic retentions and enantioselective separations were examined by linear regression analysis and the construction of quantitative structure-enantioselective retention relationships. Competitive displacement studies were also conducted using R-ibuprofen as the displacing agent. The results indicate that the enantioselective retention of the solutes takes place at the indole-benzodiazepine site (site II) on the HSA molecule and that chiral recognition is affected by the hydrophobicity and steric volume of the solutes. The displacement studies also identified a cooperative allosteric interaction induced by the binding of R-ibuprofen to site II.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università di Bologna, Italy.
authors.forename: V
authors.initials: V
authors.lastname: Andrisano
authors.forename: T D
authors.initials: TD
authors.lastname: Booth
authors.forename: V
authors.initials: V
authors.lastname: Cavrini
authors.forename: I W
authors.initials: IW
authors.lastname: Wainer
mesh_terms: D001665:Binding Sites; D001667:Binding, Competitive; D002264:Carboxylic Acids / Q000302:isolation & purification*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D006801:Humans; D008958:Models, Molecular; D012709:Serum Albumin / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D012709:Serum Albumin; D012997:Solvents