Analytical Sciences

Chiral Separation by Electrokinetic Capillary Chromatography Using Newly Synthesized Linear Polymers Containing L-Amino Acid Moieties

Masaki HAMADA and Akira DOBASHI 

Tokyo University of Pharmacy and Life Science, School of Pharmacy, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan

Chiral linear polymers were prepared by the thermal polymerization of N-acryloyl-L-valine and N-acryloyl-L-alanine derivatives using 3-mercaptopropionic acid (3-MPA) as a radical transfer agent. C-Terminal groups of the derivatives were methyl and tert-butyl esters later removed, and N-methylamide moieties. The N'-methylamide derivative of N-acryloyl-L-valine was copolymerized with its methyl ester at a molar mixing ratio of 1:1. The ester groups were removed to provide anionic linear polymers terminated with carboxylic acid of the amino acid residue. The polymers are thus shown to function as pesudostationary phases that separate enantiomeric solutes in electrokinetic capillary chromatography (EKC). Racemic 3,5-dinitrobenzoylamino isopropyl esters were separated with the polymer derived from N-acryloyl-L-valine esters and with the copolymer from N-acryloyl-L-valine methyl ester and N-acryloyl-L-valine N'-methylamide at pH 7.0. These separations could not be observed at pH 9.0 in migrating solutions containing anionic linear polymers. This pH dependence can be discussed from the standpoint of the microscopic hydrophobicity of the polymers, as assessed from the fluorescence of pyrene adsorbed onto the polymers in water.

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