Synthesis, chromatographic resolution and chiroptical properties of carboxyibuprofen stereoisomers: major metabolites of ibuprofen in man.
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.
Tan
S C
SC
Department of Pharmacy, King's College London, United Kingdom.
Baker
J A
JA
Stevens
N
N
deBiasi
V
V
Salter
C
C
Chalaux
M
M
Afarinkia
K
K
Hutt
A J
AJ
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007052:Ibuprofen