Chiral recognition by fluorescent chemosensors based on N-dansyl-amino acid-modified cyclodextrins |
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Authors: | Ikeda Hiroshi Li Qun Ueno Akihiko |
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Affiliation: | Department of Bioengineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B44 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. hikeda@bio.titech.ac.jp |
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Abstract: | Four kinds of N-dansyl-amino acid-modified beta-cyclodextrins (beta-CDs) were prepared as fluorescent chemosensors for chiral discrimination. The use of an amino acid as a spacer improved binding affinities and chiral discrimination abilities of the chemosensors. N-dansyl-l-Phe-modified beta-CD showed high d-selectivity for norbornane derivatives and N-dansyl-d-Phe-modified beta-CD showed high l-selectivity for menthol. Microcalorimetric titration results indicate that the chemosensors selectively accommodate the enantiomer that induces the least unfavorable entropy change on making an inclusion complex. |
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