Chiral recognition by fluorescent chemosensors based on N-dansyl-amino acid-modified cyclodextrins.
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.
Ikeda
Hiroshi
H
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
Li
Qun
Q
Ueno
Akihiko
A
D000596:Amino Acids / Q000737:chemistry*; D015374:Biosensing Techniques / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000596:Amino Acids; D003505:Cyclodextrins; D005456:Fluorescent Dyes