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Chiral high performance liquid chromatographic separation of enantiomers of alpha-methyl alpha-amino acids

, : Chiral high performance liquid chromatographic separation of enantiomers of alpha-methyl alpha-amino acids. Journal of Liquid Chromatography & Related Technologies 23(7): 1061-1068, April

The enantiomeric separation by chiral high performance liquid chromatography of derivatized and underivatized alpha-methyl alpha-amino acids was achieved by two different methods. A cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase column (Daicel Chiralcel OD) was used to resolve N-benzyloxycarbonylated methyl esters. Excellent separations of enantiomers were achieved with all the alpha-methyl alpha-amino acids examined. A column packed with octadecylsilanized silica coated with N,S-dioctyl-D-penicillamine as a chiral ligand-exchange phase (Sumichiral OA-5000) was also used to resolve the underivatized amino acids. Excellent to good separations of enantiomers were achieved with a variety of underivatized alpha-methyl alpha-amino acids carrying aliphatic or aromatic side-chains by optimizing the amount of the organic component and the concentration of the copper(II) ion in the hydro-organic eluent.

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