Ferrocene derivatization reagents for optical resolution of carboxylic acids by high-performance liquid chromatography with electrochemical detection

Kazutake Shimada, Emi Haniuda, Tomoyuki Oe, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

New derivatization methods using chiral ferrocene reagents have been developed for the optical resolution of carboxylic acids by high-performance liquid chromatography with electrochemical detection. Two chiral derivatization reagents, 1-ferrocenylethylamine and 1-ferrocenylpropylamine, were readily prepared from acetyl ferrocene and propionylferrocene in two steps, respectively. Condensation of carboxylic acids with the chiral reagent was effected in the presence of water-soluble carbodiimide and 1-hydroxybenzotriazole. The diastereomeric amides formed from N-acetylamino acid and α-arylpropionic acid enantiomers were efficiently resolved by reversed-phase chromatography and showed the satisfactory sensitivity at +0.45 V vs. an Ag/AgCl reference electrode with a detection limit of 0.5 pmole (S/N=5).

Original languageEnglish
Pages (from-to)3161-3172
Number of pages12
JournalJournal of Liquid Chromatography
Volume10
Issue number14
DOIs
Publication statusPublished - 1987 Oct 1

ASJC Scopus subject areas

  • Molecular Medicine

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