Enantioselective separation of chiral arylcarboxylic acids on an immobilized human serum albumin chiral stationary phase.
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.
Andrisano
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Dipartimento di Scienze Farmaceutiche, Università di Bologna, Italy.
Booth
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TD
Cavrini
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Wainer
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IW
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
D002264:Carboxylic Acids; D012709:Serum Albumin; D012997:Solvents