Chiral resolution of enantiomeric steroids by high-performance liquid chromatography on amylose tris(3,5-dimethylphenylcarbamate) under reversed-phase conditions

Amylose tris(3,5-dimethylphenylcarbamate) (Chiralpak AD) was used under reversed-phase conditions for the chiral separation of 26 steroids. It was found that the chiral separation behavior of Chiralpak AD under reversed-phase conditions differs clearly from those under normal-phase conditions thereb...

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Bibliographic Details
Published inJournal of Chromatography A Vol. 825; no. 2; pp. 107 - 114
Main Authors Kummer, Matthias, Werner, G.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 06.11.1998
Elsevier
Subjects
Analysis
Analytical chemistry
Biological and medical sciences
Chemistry
Chromatographic methods and physical methods associated with chromatography
Estradiol
Exact sciences and technology
General pharmacology
Medical sciences
Other chromatographic methods
Pharmacology. Drug treatments
Steroids
Chiral stationary phases, LC
Estradiol
Enantiomer separation
Amylose tris(3,5-dimethylphenylcarbamate) stationary phases
Steroids
Steroid
Separation
Phase composition
Amylose derivative
Estrogen
HPLC chromatography
Temperature effect
Chiral stationary phase
Experimental study
Mobile phase
Organic carbamate
Progestagen
Reversed phase chromatography
Ultraviolet detector
Optical resolution
Enantiomer
Contraceptive
Anabolic agent
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Summary:Amylose tris(3,5-dimethylphenylcarbamate) (Chiralpak AD) was used under reversed-phase conditions for the chiral separation of 26 steroids. It was found that the chiral separation behavior of Chiralpak AD under reversed-phase conditions differs clearly from those under normal-phase conditions thereby extending the range of application of this chiral stationary phase. The substitution of methanol for acetonitrile in the aqueous eluent did not grossly change the chiral separation behavior. The enantioselectivity under reversed-phase conditions is strongly dependent on the water concentration in the eluent up to 10%. The influence of the temperature on the chiral separation is discussed from a practical point of view. A HPLC method for the quantification of the unnatural enantiomer of estradiol in drug substances applying Chiralpak AD under reversed-phase conditions was developed and successfully validated.
ISSN:0021-9673
DOI:10.1016/S0021-9673(98)00719-5