Chiral discrimination of primary amines by HPLC after labeling with a chiral derivatization reagent, trans-2-(2,3-anthracenedicarboximido)-cyclohexanecarbonyl chloride

✍ Scribed by Kazuaki Akasaka; Takashi Ohtaki; Hiroshi Ohrui

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 998 KB
• Volume: 29
• Category: Article
• ISSN: 1615-9306
• DOI: 10.1002/jssc.200600025

✦ Synopsis

Abstract

Enantiomeric discrimination of chiral primary amines was performed by both reversed‐phase HPLC and normal‐phase HPLC after labeling with a chiral fluorescent derivatization reagent, (1__R__,2__R__)‐ and (1__S__,2__S__)‐trans‐2‐(2,3‐anthracenedicarboximido)cyclohexanecarbonyl chloride. Use of HPLC permits separation of diastereomeric derivatives of amines up to C30 which have a primary amino group at the middle of the alkyl chain. The derivatives of primary amines having an anteiso alkyl chain, which has a chiral branched‐methyl at the n‐3 position of the alkyl chain, were also separated by HPLC, and it was also possible to separate niphatesine D by reversed‐phase HPLC after derivatization.