Ikeda Hiroshi, Li Qun, Ueno Akihiko
Department of Bioengineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B44 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan.
Bioorg Med Chem Lett. 2006 Oct 15;16(20):5420-3. doi: 10.1016/j.bmcl.2006.07.069. Epub 2006 Aug 4.
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.
制备了四种N-丹磺酰基氨基酸修饰的β-环糊精（β-CD）作为用于手性识别的荧光化学传感器。使用氨基酸作为间隔基提高了化学传感器的结合亲和力和手性识别能力。N-丹磺酰基-l-苯丙氨酸修饰的β-CD对降冰片烷衍生物表现出高d-选择性，而N-丹磺酰基-d-苯丙氨酸修饰的β-CD对薄荷醇表现出高l-选择性。微量热滴定结果表明，化学传感器选择性地容纳在形成包合物时引起最不利熵变最小的对映体。
