Relationship between chromatographic resolution and amide structure of chiral 2-hydroxy acids as O-(?)-menthoxycarbonylated diastereomeric derivatives for enantiomeric separation on achiral gas chromatography

Title
Relationship between chromatographic resolution and amide structure of chiral 2-hydroxy acids as O-(?)-menthoxycarbonylated diastereomeric derivatives for enantiomeric separation on achiral gas chromatography
Authors
차은주김소희이강미김호준김기훈권오승박기덕이재익
Issue Date
2016-02
Publisher
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences
Citation
VOL 1012, 17-22
Abstract
The relationship between chromatographic resolution and amide structure of chiral 2-hydroxy acids as O-(−)-menthoxycarbonylated diastereomeric derivatives on achiral gas chromatography was investigated to elucidate the best diastereomeric conformation for enantiomeric separation of chiral 2-hydroxy acids. Thirteen chiral 2-hydroxy acids were converted into nine different diastereomeric O-(−)-menthoxycarbonylated amide derivatives using the primary, secondary and cyclic amines to achieve complete enantiomeric separation through an achiral column. Each enantiomeric pair of 2-hydroxy acids as O-(−)-menthoxycarbonylated tert-butylamide derivatives was resolved on both the DB-5 and DB-17 columns with resolution factors ranging from 1.7 to 4.8 and 1.7 to 3.4, respectively. The results revealed that the structure of the amide moiety is shown to significantly affect chromatographic resolution. In addition, O-(−)-menthoxycarbonylated tert-butylamide derivatives were shown to be the best diastereomeric conformations for enantiomeric separation of 2-hydroxy acids. When comparing with our previous O-trifluoroacetylated(−)-menthyl ester derivatization method, the present results suggested that size differences between groups attached to the chiral center and conformational rigidity can have stronger effects on resolution than the distance between chiral centers. The elution of R- and S-stereoisomers was affected by the class of amine; i.e., primary, secondary, or cyclic, regardless of the substituents on the amine group, the structure of the 2-hydroxy acid, and the polarity of the column.
URI
http://pubs.kist.re.kr/handle/201004/58456
ISSN
15700232
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