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Enantiomeric and diastereomeric high-performance liquid chromatographic separation of cyclic β-substituted α-amino acids on a copper(II)-d-penicillamine chiral stationary phase by Michael Schlauch; Franz-Josef Volk; Kamalesh Pai Fondekar; Judith Wede; August W Frahm is a Chemistry article available to read on EtoBox.

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High-performance liquid chromatographic (HPLC) separation of stereoisomeric cyclic b-substituted a-quaternary a-amino acids was performed by ligand-exchange on a copper(II)-D-penicillamine chiral stationary phase. The investigated amino acids are the 1-amino-2-methylcyclohexanecarboxylic acids, the 1-amino-2-hydroxycyclohexanecarboxylic acids, the 1amino-2-methylcyclopentanecarboxylic acids and the trans-configured 1,2-diaminocyclohexanecarboxylic acids. The effects of the mobile phase composition (copper(II) concentration, type and content of organic modifier, pH) and the temperature on the enantio-and diastereoselectivity were studied and the conditions were optimised to resolve the four stereoisomers of each of the said amino acids in single chromatographic runs. A reversal of the elution order occurred for enantiomers of some of the amino acids in dependence on the acetonitrile content of the eluent. This phenomenon is explained by at least two different copper(II) complexes of the tridentate ligand penicillamine.

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Author

Michael Schlauch; Franz-Josef Volk; Kamalesh Pai Fondekar; Judith Wede; August W Frahm

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 1873-3778)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)