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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 4
BKCSDE 16(4)
April 20, 1995

Title	Chiral Recognition Models of Enantiomeric Separation on Cyclodextrin Chiral Stationary Phases
Author	Sun Haing Lee*, Byoung Hak Kim, Young Cheol Lee
Keywords
Abstract	The enantiomeric separation of several amino acid derivatives by reversed-phase liquid chromatography using two (R)-and (S)-naphthylethylcarbamate-β -cyclodextrin(NEC-β-CD) bonded stationary phases was studied to illustrate the chiral recognition model of the enantiomeric separation. The retention and enantioselectivity of the chiral separations with (R)-and (S)-NEC-β-CD bonded phases were compared with similar separations with the native β-CD stationary phases. Especially, the enantioselectivity and elution orders between the derivatized amino acid enantiomers are carefully examined. These results can be illustrated by the chiral recognition models involving inclusion complexation, π-π interaction, and/or hydrophobic interaction. Inclusion complexation and hydrophobic interaction of the naphthyl group of the NEC moiety seem to be major chiral recognition components in the enantiomeric separation of 2,4-dinitrophenyl amino acids and dabsyl amino acids on (R)-and (S)-NEC-β-CD columns. For dansyl amino acids, only the inclusion complexation is the dominant factor. Three different chiral recognition models containing π-π interaction, inclusion complexation and hydrogen bonding were proposed for the separation of the 3,5-dinitrobenzoyl amino acid enantiomers, depending on the size and shape of amino acids.
Page	305 - 309
Full Text	PDF

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