Enantioselective separation of chiral arylcarboxylic acids on an immobilized human serum albumin chiral stationary phase

✍ Scribed by V. Andrisano; T. D. Booth; V. Cavrini; I. W. Wainer

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 160 KB
• Volume: 9
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1997)9:2<178::aid-chir19>3.0.co;2-k

✦ Synopsis

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 structureenantioselective 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.