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Optically Selective Adsorption of α-Amino Acids on Montmorillonite-Cu-1-Lysine Complexes in High-Pressure Liquid Chromatography

Published online by Cambridge University Press:  02 April 2024

Faina Tsvetkov  and
U. Mingelgrin
Faina Tsvetkov
Affiliation:
Institute of Soils and Water, Agricultural Research Organization, P.O. Box 6, The Volcani Center, Bet Dagan 50-250, Israel
U. Mingelgrin
Affiliation:
Institute of Soils and Water, Agricultural Research Organization, P.O. Box 6, The Volcani Center, Bet Dagan 50-250, Israel
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Abstract

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Optically active cationic complexes adsorbed on montmorillonite can be used for the resolution of racemic mixtures. Montmorillonite-Cu-lysine systems were used as a solid phase in high-pressure liquid chromatography for the resolution of the optical isomers of α-amino acids. Selectivity constants > 1.5 were measured for phenylalanine and tryptophan. The selectivity constants for the amino acids containing saturated-hydrocarbon side chains were in the range of 1.25–1.44. The montmorillonite-Cu-l-lysine complex displayed a stronger affinity for the l-isomers of α-amino acids than for the d-isomers at pHs near neutrality. Inasmuch as surface-catalyzed peptide formation on clays has been proposed as a step in chemical evolution, this stronger affinity between the clay-Cu-l-amino acid complex and l-amino acids might have been significant in prebiotic evolution. The mechanism of optical resolution probably involved ligand exchange. Optimizing the choice of the optically active ligands and of the chelating cation in the chiral agent may improve the resolution of the optical isomers.

Keywords

AdsorptionAmino acidCu-1-lysineHigh-pressure liquid chromatographyMontmorilloniteOptically active ligands
Type
Research Article
Information
Clays and Clay Minerals , Volume 35 , Issue 5 , October 1987 , pp. 391 - 399
Copyright
Copyright © 1987, The Clay Minerals Society

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