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Enantiomer separation of amino acids as theirN-alkyloxycarbonyl alkylamide derivatives by chiral phase capillary GC

✍ Scribed by Abe, Iwao ;Nakahara, T.

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 351 KB
Volume: 19
Category: Article
ISSN: 0935-6304
DOI: 10.1002/jhrc.1240190907

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✦ Synopsis

Abstract

The enantiomers of amino acids were first converted into N‐alkyloxycarbonyl 2,2,2‐trifluoroethyl esters, and then into N‐alkyloxycarbonyl alkylamides by nucleophilic substitution of the ester group with amines. The first reaction proceeds instantaneously, while the second substitution occurs smoothly with n‐propylamine and isobutylamine. The final derivatives were produced for separation on a capillary column coated with Chirasil‐Val by GC. Pro, which is difficult to separate completely as its N‐perfluoroacyl alkyl ester derivative, showed complete separation of the enantiomeric pair. All amino acids examined in this study showed an increased separation factor.

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