Resolution of enantiomeric steriod by high-performance liquid chromatography on chiral stationary phases

The chiral separation of 11 steroids was investigated on amylose tris(3,5-dimethylphenyl carbamate) (Chiralpak AD). This chiral stationary phase was subjected to both normal-phase and reversed-phase conditions. Enantioselectivities were higher in the reversed-phase mode for the majority of steroids....

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Bibliographic Details
Published inJournal of Chromatography A Vol. 749; no. 1; pp. 61 - 68
Main Authors Kummer, Matthias, Palme, H.-J., Werner, G.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.10.1996
Subjects
Chiral stationary phases, LC
Enantiomer separation
Steroids
Chiral stationary phases, LC
Enantiomer separation
Steroids
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Summary:The chiral separation of 11 steroids was investigated on amylose tris(3,5-dimethylphenyl carbamate) (Chiralpak AD). This chiral stationary phase was subjected to both normal-phase and reversed-phase conditions. Enantioselectivities were higher in the reversed-phase mode for the majority of steroids. The influence of structural modifications of the steroid molecule on the chiral separation was investigated. Acetylation of hydroxyl groups decreased enantioselectivity in the normal-phase mode. However, some acetates exhibited higher enantioselectivities in the reversed-phase mode. The type of alkyl substitution had opposite effects under normal-phase and reversed-phase condistions. The reversed-phase eleuent probably chnages the chiral recognition characteristics of amylose tris(3,5-dimethylphenyl carbamate). All 11 steroids were also chromatographed on permethylated β- and γ-cyclodextrin columns. Enantioselectivities were lower compared to the amylose column, with the β-cyclodextrin being superior to the γ-cyclodextrin.
ISSN:0021-9673
DOI:10.1016/0021-9673(96)00364-0