Enantiomeric and diastereomeric high-performance liquid chromatographic separation of cyclic beta-substituted alpha-amino acids on a copper(II)-D-penicillamine chiral stationary phase.
High-performance liquid chromatographic (HPLC) separation of stereoisomeric cyclic beta-substituted alpha-quaternary alpha-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 1-amino-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.
Schlauch
M
M
Department of Pharmaceutical Chemistry, University of Freiburg, Germany.
Volk
F J
FJ
Fondekar
K P
KP
Wede
J
J
Frahm
A W
AW
D000598:Amino Acids, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D010396:Penicillamine / Q000737:chemistry*; D013237:Stereoisomerism
D000598:Amino Acids, Cyclic; D010396:Penicillamine