Sensitive Enantiomeric Separation of Aliphatic and Aromatic Amines using Aromatic Anhydrides as Non-Chiral Derivatizing Agents

Abstract

New pre-column derivatizing reagents: phthalic anhydride, 3-nitrophthalic anhydride, diphenic anhydride, 1,8-naphthalic anhydride and diphenylmaleic anhydride have been developed for resolving chiral compounds having amine groups. Although all of these agents produce derivatives with high molar absorptivities, the later two also fluoresce. Upon derivatization, aromatic analytes containing free carboxylic groups are produced. Both of these moieties enhance chiral recognition on cyclodextrin-based columns. The derivatization reaction is carried out at room temperature by shaking a buffered aqueous solution of a sample with an acetonitrile solution of the reagent. The reaction is fast and proceeds without any detectable racemization. The labeled compounds have favorable chromatographic properties which are demonstrated by resolution of a number of chiral compounds on cyclodextrin-bonded phases operated with non-aqueous polar organic eluents. The selectivity and good efficiency of this system contributes to its high sensitivity and in its applicability for detecting low levels of enantiomeric impurities. The detection limit is in the picomole range and less than 0.1% enantiomeric impurities can be determined in some cases. © 1994.

Department(s)

Chemistry

Comments

National Institute of General Medical Sciences, Grant NIH BMT 2ROl GM36292-0542

International Standard Serial Number (ISSN)

0021-9673

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2024 Elsevier, All rights reserved.

Publication Date

22 Apr 1994

PubMed ID

7802865

Link to Full Text

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