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 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.
Paik
Man-Jeong
MJ
College of Pharmacy, Sungkyunkwan University, 300 Chunchun-dong, Jangan-ku, Suwon, Kyunggi-do 440-746, South Korea.
Lee
Yoonsuk
Y
Goto
Junichi
J
Kim
Kyoung-Rae
KR
D000577:Amides / Q000737:chemistry*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000032:analysis* / Q000737:chemistry; D002849:Chromatography, Gas / Q000295:instrumentation*; D012015:Reference Standards; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000577:Amides; D000894:Anti-Inflammatory Agents, Non-Steroidal