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Determination of the enantiomers of α-amino acids and α-amino acid amides by high-performance liquid chromatography with a chiral mobile phase

✍ Scribed by A. Duchateau; M. Crombach; M. Aussems; J. Bongers

Publisher
Elsevier Science
Year
1989
Tongue
English
Weight
716 KB
Volume
461
Category
Article
ISSN
1873-3778

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✦ Synopsis

A high-performance liquid chromatographic method for the enantiomeric analysis of a mixture of an a-amino acid and the corresponding acid amide is described. Reversed-phase chromatography with copper(I1) acetate and N,N-di-n-propyl-Lalanine in the mobile phase are used for the separation. For Val and Val-NH2, several parameters affecting retention and enantioselectivity were investigated. The results indicate that by manipulation of pH, ionic strength, temperature, concentration of Cu", N,N-di-n-propyl-L-alanine and ion-pairing reagent, good control of enantiomeric separation can be achieved. For a-amino acid amides a mechanism is proposed which may account for the retention and enantioselectivity. Examples of enantiomeric analysis of mixtures of a-amino acids and a-amino acid amides with aliphatic, aromatic and polar side-chains are given. The method can be used for the control of the enantiomeric purity of a-amino acids and the corresponding acid amides obtained by enantioselective synthesis.

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