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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 9
BKCSDE 23(9)
September 20, 2002 

Liquid Chromatographic Resolution of N-Protected α-Amino Acids as Their Anilide and 3,5-Dimethylanilide Derivatives on Chiral Stationary Phases Derived from (S)-Leucine
Myung Ho Hyun, Yoon Jae Cho, In Kyu Baik
Liquid chromatography, Enantioseparation, Chiral stationary phase, a-Amino acids
Various racemic N-protected α-amino acids such as N-t-BOC-(tert-butoxycarbonyl), N-CBZ-(benzyloxycarbonyl) and N-FMOC-(9-fluorenylmethyloxycarbonyl) α-amino acids were resolved as their anilide and 3,5-dimethylanilde derivatives on an HPLC chiral stationary phase (CSP) developed by modifying a commercial (S)-leucine CSP. The chromatographic resolution results were compared to those on the commercial (S)-leucine CSP. The resolutions were greater on the modified CSP than those on the commercial CSP with only one exception, the resolution of N-t-BOC-phenylglycine anilide. In addition, the chromatographic resolution behaviors were quite consistent except for the resolution of N-protected phenylglycine derivatives, the (S)-enantiomers being retained longer. Based on the chromatographic resolution behaviors and with the aid of CPK molecular model studies, we proposed a chiral recognition mechanism for the resolution of N-protected α-amino acid derivatives. However, for the resolution of N-protected phenylglycine derivatives, a second chiral recognition mechanism, which competes in the opposite sense with the first chiral recognition mechanism, was proposed. The two competing chiral recognition mechanisms were successfully used in the rationalization of the chromatographic behaviors for the resolution of N-protected phenylglycine derivatives.
1291 - 1296
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