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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 10, Number 6
BKCSDE 10(6)
June 20, 1989 

Optical Resolution of Dansyl Amino Acids with Addition of Benzyl-L-Hydroxyproline Copper(Ⅱ) Chelate by High Performance Liquid Chromatography
Sun Haing Lee*, Tae Sub Oh, Sang Hyun Bak
Resolution of enantiomers of DNS-amino acids has been achieved by a reversed phase liquid chromatography with an addition of a copper(Ⅱ) complex of N-benzyl-L-hydroxyproline to the mobile phase. N-Benzyl-L-hydroxyproline was prepared and used as a chiral ligand of copper(Ⅱ) chelate for the optical resolution. The pH and the concentration of copper(Ⅱ) chelate, organic solvent, and buffer agent in the mobile phase all affect the optical resolutions of dansyl amino acids. The elution orders between D and L-DNS-amino acids were different depending on the structure of the side chain of the amino acids. The retention mechanism for the chiral separation of the dansyl amino acids can be illustrated by the equilibrium of ligand exchange and by hydrophobic interaction with C18 stationary phase. The chiral separation can be illustrated with cis and trans effect of the ligand exchange reaction.
491 - 495
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