title: Synthesis, chromatographic resolution and chiroptical properties of carboxyibuprofen stereoisomers: major metabolites of ibuprofen in man.
abstract: The chromatographic resolution of the four stereoisomers of carboxy-ibuprofen, a major metabolite of ibuprofen in man, was achieved using a Chiralpak AD chiral stationary phase (CSP) (J.T. Baker, Milton, Keynes, UK). The elution order of the stereoisomers was determined to be 2'S,2R;2'R,2R;2'R,2S;2'S,2S by a combination of stereoselective synthesis of diastereoisomeric mixtures and analysis of the two diastereoisomers isolated from human urine following the administration of (S)-ibuprofen. The individual stereoisomers were isolated by semipreparative chiral phase chromatography and characterized by circular dichroism spectroscopy.
authors.affiliation: Department of Pharmacy, King's College London, United Kingdom.
authors.forename: S C
authors.initials: SC
authors.lastname: Tan
authors.forename: J A
authors.initials: JA
authors.lastname: Baker
authors.forename: N
authors.initials: N
authors.lastname: Stevens
authors.forename: V
authors.initials: V
authors.lastname: deBiasi
authors.forename: C
authors.initials: C
authors.lastname: Salter
authors.forename: M
authors.initials: M
authors.lastname: Chalaux
authors.forename: K
authors.initials: K
authors.lastname: Afarinkia
authors.forename: A J
authors.initials: AJ
authors.lastname: Hutt
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002942:Circular Dichroism; D006801:Humans; D007052:Ibuprofen / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D055095:Optics and Photonics; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D007052:Ibuprofen