Liquid Chromatographic Resolution Of Enantiomers Containing Single Aromatic Rings With Β-cyclodextrin-bonded Phases

Abstract

Racemic compounds containing two or more ring moieties are thought to be of optimal size for complexation and resolution on β-cyclodextrin (β-CD) bonded-phase liquid chromatographic columns. There are few reports on the separation of racemates containing one or no rings. Here, seventeen single-ring-containing racemates are resolved via β-CD complexation: (±)-1-phenyl- ethyl propionate; (±)-α-methylbenzyl acetate, (±)-2-chloro-2-phenylacetic acid, (±)-ethyl- 3-phenylglycidate, d,l-3,4-dihydroxyphenyl-α-propylacetamide; (±)-2-methoxy-α-methylbenzyl alcohol, d,l-2-phenylpropionaldehyde, d,l-α-amino-3-thiopheneacetic acid, (±)-mandelic acid, (±)-mandelic acid methyl ester, (±)-O-acetylmandelic acid, (±)-ephedrine; d,l-phenyl- alanineamide, d,l-tyrosine, d,l-tyrosine methyl ester, 3-hydroxy-d,l-kynurenine and N-(3,5- dinitrobenzoyl)-d,l-leucine. These compounds can be separated on β-CD media, and have certain common structural properties that enhance chiral recognition. The factors that permit the resolution of single-ring-containing racemates on β-CD columns are discussed. © 1988.

Department(s)

Chemistry

Comments

National Institute of General Medical Sciences, Grant BMT lRO1 GM 36292-02

International Standard Serial Number (ISSN)

0003-2670

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2023 Elsevier, All rights reserved.

Publication Date

01 Jan 1988

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