Derivatized cyclodextrins for normal-phase liquid chromatographic separation of enantiomers

Several different derivatized {beta}-cyclodextrins were synthesized and used as chiral stationary phases in normal-phase liquid chromatography. The multiply substituted derivatives were made with acetic anhydride, (R)- and (S)-1-(1-naphthyl)ethyl isocyanate, 2,6-dimethylphenyl isocyanate, and p-tolu...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 1990-08, Vol.62 (15), p.1610-1615
Main Authors: Armstrong, Daniel W, Stalcup, Apryll M, Hilton, Martha L, Duncan, Jo Dee, Faulkner, James R, Chang, San Chun
Format: Article
Language:English
Subjects:
400102 - Chemical & Spectral Procedures
Analytical chemistry
CALCULATION METHODS
CARBOHYDRATES
Chemistry
Chromatographic methods and physical methods associated with chromatography
CHROMATOGRAPHY
DEXTRIN
ENANTIOMORPHS
Exact sciences and technology
EXTRACTION APPARATUSES
EXTRACTION COLUMNS
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
LIQUID COLUMN CHROMATOGRAPHY
MEASURING METHODS
ORGANIC COMPOUNDS
Other chromatographic methods
POLYSACCHARIDES
SACCHARIDES
SEPARATION EQUIPMENT
SEPARATION PROCESSES
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Summary:Several different derivatized {beta}-cyclodextrins were synthesized and used as chiral stationary phases in normal-phase liquid chromatography. The multiply substituted derivatives were made with acetic anhydride, (R)- and (S)-1-(1-naphthyl)ethyl isocyanate, 2,6-dimethylphenyl isocyanate, and p-toluoyl chloride. The first successful cyclodextrin-based, normal-phase separation of enantiomers was accomplished on these derivative phases. In contrast to chiral separations on the native {beta}-cyclodextrin stationary phase, the enantiomeric separation mechanism on these new phases is not thought to be dependent on inclusion complexation. The similarities and differences between the derivatized cyclodextrin stationary phases and the cellulosic stationary phases are discussed.
ISSN:0003-2700
1520-6882
DOI:10.1021/ac00214a014