Chiral discrimination of multiple profens as diastereomeric ( R)-(+)-1-phenylethylamides by achiral dual-column gas chromatography

Profens were converted into diastereomeric ( R)-(+)-1-phenylethylamides using ethyl chloroformate and triethylamine in dichloromethane. Gas chromatographic analysis on dual-columns with different polarities provided complete enantioresolution of eight profens, facilitating chiral discrimination base...

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Bibliographic Details
Published in:Journal of chromatography. B, Analytical technologies in the biomedical and life sciences Analytical technologies in the biomedical and life sciences, 2004-04, Vol.803 (2), p.257-265
Main Authors: Paik, Man-Jeong, Lee, Yoonsuk, Goto, Junichi, Kim, Kyoung-Rae
Format: Article
Language:English
Subjects:
( R)-(+)-1-Phenylethylamides
Amides - chemistry
Analysis
Analytical, structural and metabolic biochemistry
Anti-Inflammatory Agents, Non-Steroidal - analysis
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Biological and medical sciences
Chromatography, Gas - instrumentation
Enantiomer separation
Fundamental and applied biological sciences. Psychology
General pharmacology
Medical sciences
Pharmacology. Drug treatments
Profens
Reference Standards
Reproducibility of Results
Stereoisomerism
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Summary:Profens were converted into diastereomeric ( R)-(+)-1-phenylethylamides using ethyl chloroformate and triethylamine in dichloromethane. Gas chromatographic analysis on dual-columns with different polarities provided complete enantioresolution of eight profens, facilitating chiral discrimination based on matching with retention index sets characteristic of each enantiomer. The present method was linear ( r≥0.9992) with good precision (0.8–6.0%) and accuracy (−9.3 to 0.003%), allowing detection of trace ( R)-profens in optical purity test on four ( S)-profen mixture in a single run. And the method allowed simultaneous enantiomeric screening for ibuprofen enantiomers and their chiral metabolites excreted in urine following administration of racemic ibuprofen.
ISSN:1570-0232
1873-376X
DOI:10.1016/j.jchromb.2003.12.026