Planar Chromatographic Separation Of Enantiomers And Diastereomers With Cyclodextrin Mobile Phase Additives

Abstract

A variety of racemic compounds were resolved using reversed-phase thin-layer chromatography (TLC) with mobile phases containing highly concentrated solutions of β-cyclodextrin (β-CD) These include the drugs labetalol and mephenytoin, metallocenes, crown ethers, methyl-p-toluenesulfinate, nornicotine derivatives and several dansyl and β-naphthylamide substituted amino acids.It was possible to resolve some racemates that could not be separated on β-CD bonded phase liquid chromatography (LC) columns with this technique. Likewise there were some compounds that could be resolved with the LC approach that failed to separate with the present TLC method. In cases of racemates that could be resolved by either approach, it was found that the retention order was exactly opposite for the two methods. Enantiomeric resolution is highly dependent on mobile phase composition. In particular, the type and amount of organic modifier as well as the concentration of β-CD affect the observed resolution. Possible reasons for the chromatographic behavior are discussed. Several diastereoisomeric compounds were separated as well, including steroid epimers and pharmaceutical compounds. © 1988.

Department(s)

Chemistry

Comments

National Institute of General Medical Sciences, Grant R01GM036292

International Standard Serial Number (ISSN)

0021-9673

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2023 Elsevier, All rights reserved.

Publication Date

01 Jan 1988

PubMed ID

3243840

Link to Full Text

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