Synthesis, chromatographic resolution and chiroptical properties of carboxyibuprofen stereoisomers: Major metabolites of ibuprofen in man
✍ Scribed by Soo Choon Tan; James A. Baker; Nichola Stevens; Vern de Biasi; Colin Salter; Maria Chalaux; Kamyar Afarinkia; Andrew J. Hutt
- Book ID
- 101294547
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 383 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
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.