Development of a capillary electrophoretic method for the separation of diastereoisomers of a new human immunodeficiency virus protease inhibitor

A capillary electrophoretic (CE) method was developed for the separation of diastereoisomers of a new human immunodeficiency virus (HIV) protease inhibitor TMC114. In total 16 isomers of this drug have been synthesized (eight pairs of enantiomers). We succeeded in the separation of the eight diaster...

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Bibliographic Details
Published in:Electrophoresis 2005-02, Vol.26 (3), p.627-632
Main Authors: Leonard, Stefanie, Van Schepdael, Ann, Iványi, Tímea, Lázár, István, Rosier, Jan, Vanstockem, Marc, Vermeersch, Hans, Hoogmartens, Jos
Format: Article
Language:English
Subjects:
Acetonitriles
Capillary electrophoresis
Crown Ethers
Darunavir
Electrophoresis, Capillary - instrumentation
Electrophoresis, Capillary - methods
Emulsions
HIV Protease Inhibitors - isolation & purification
Isomers
Protease inhibitor
Sensitivity and Specificity
Stereoisomerism
Sulfonamides - isolation & purification
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Summary:A capillary electrophoretic (CE) method was developed for the separation of diastereoisomers of a new human immunodeficiency virus (HIV) protease inhibitor TMC114. In total 16 isomers of this drug have been synthesized (eight pairs of enantiomers). We succeeded in the separation of the eight diastereoisomers, but no enantiomers could be separated. Because of the high similarity and water‐insolubility of these isomers, the separation is a real challenge. Different CE modes were tried out: capillary zone electrophoresis (CZE), nonaqueous capillary electrophoresis (NACE), micellar electrokinetic capillary chromatography (MEKC), and microemulsion electrokinetic capillary chromatography (MEEKC). Only MEEKC offered resolution of these compounds.
ISSN:0173-0835
1522-2683
DOI:10.1002/elps.200406147