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Synthesis, chromatographic resolution and chiroptical properties of carboxyibuprofen stereoisomers: Major metabolites of ibuprofen in man
Author(s) -
Tan Soo Choon,
Baker James A.,
Stevens Nichola,
de Biasi Vern,
Salter Colin,
Chalaux Maria,
Afarinkia Kamyar,
Hutt Andrew J.
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:1<75::aid-chir14>3.0.co;2-n
Subject(s) - diastereomer , chemistry , ibuprofen , metabolite , chromatography , resolution (logic) , elution , circular dichroism , stereoselectivity , enantiomer , stereoisomerism , stereochemistry , chiral column chromatography , high performance liquid chromatography , organic chemistry , catalysis , medicine , biochemistry , artificial intelligence , computer science , pharmacology
The chromatographic resolution of the four stereoisomers of carboxyibuprofen, 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 ,2 R ; 2′ R ,2 R ; 2′ R ,2 S ; 2′ S ,2 S 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. Chirality 9:75–87, 1997. © 1997 Wiley‐Liss, Inc.