HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIC METHOD FOR THE SEPARATION OF THE OPTICAL ISOMERS OF GAMMA,GAMMA'-DI-TERT-BUTYL-D,L-GAMMA-CARBOXYGLUTAMIC ACID AND D,L-GAMMA-CARBOXYGLUTAMIC ACID

摘要

The chemical synthesis of gamma,gamma'-di-tert.-butyl-gamma-carboxyglutamic acid is accompanied by extensive racemization, and very careful resolution is needed to obtain D- and L-gamma,gamma'-di-tert.-butyl-gamma-carboxyglutamic acids in high chiral purity. A novel method was devised for the separation of enantiomers of gamma,gamma'-di-tert.-butyl-gamma-carboxyglutamic acid and gamma-carboxyglutamic acid, applying precolumn derivatization with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-beta-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. [References: 46]