High-performance liquid chromatographic method for the separation of the optical isomers of γ,γ′-di-tert.-butyl-d,l-γ-carboxyglutamic acid and d,l-γ-carboxyglutamic acid

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Abstract

The chemical synthesis of γ,γ′-tert.-butyl-γ-carboxyglutamic acid is accompanied by extensive racemization, and very careful resolution is needed to obtain d- and l-γ,γ′-di-tert.-butyl-γ-carboxyglutamic acids in high chiral purity. A novel method was devised for the separation of enantiomers of γ,γ′-di-tert.-butyl-γ-carboxyglutamic acid and γ-carboxyglutamic acid, applying precolumn derivatization with 1-fluoro-2,4-dinitrophenyl-5-l-alanine amide and 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate as chiral reagents, with subsequent reversed-phase high-performance liquid chromatographic separation of diastereomeric compounds. The effects of organic modifiers, of the mobile-phase composition and of the pH on the separation of the diastereomers were investigated.

Original languageEnglish
Pages (from-to)297-302
Number of pages6
JournalJournal of Chromatography A
Volume710
Issue number2
DOIs
Publication statusPublished - Sep 1 1995

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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