Chiral Recognition of Phenylacetic Acid Derivatives by Aminated Cyclodextrins |
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| Authors: | Takashi Kitae Hiroshi Takashima Koji Kano |
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| Affiliation: | (1) Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto, 610-03, Japan |
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| Abstract: | Chiral recognition of mandelic acid ( 1), acetylmandelic acid ( 2), 1-methoxyphenylacetic acid ( 3), phenylsuccinic acid ( 4), 2-phenylpropanoic acid ( 5) and ibuprofen ( 6) in their anionic forms by protonated 6A-amino-6A-deoxy- -cyclodextrin (mono-NH3+--CD) and 6A,6D-diamino-6A,6D-dideo xy--cyclodextrin (di-NH3+--CD) has been studied by means of capillary zone electrophoresis (CZE) and 1H NMR spectroscopy. Both methods show the preferable guests for mono-NH3+--CD to be the (R)-enantiomers of 1, 3 and 5 and the (S)-enantiomers of 2, 4 and 6. Cooperative work of Coulomb interactions and inclusion is essential for chiral recognition of these anionic guests. |
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| Keywords: | chiral recognition phenylacetic acid derivatives aminated cyclodextrins capillary zone electrophoresis 1H NMR |
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