Chiral recognition by fluorescent chemosensors based on N-dansyl-amino acid-modified cyclodextrins

被引：23

作者：

Ikeda, Hiroshi ^{[1
]}

Li, Qun ^{[1
]}

Ueno, Akihiko ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Bioengn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 20期

关键词：

chemosensor; chiral discrimination; cyclodextrin; fluorescence; molecular recognition;

D O I：

10.1016/j.bmcl.2006.07.069

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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 P-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. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5420 / 5423

页数：4

共 25 条

[1] Fluorescence properties, induced-fit guest binding and molecular recognition abilities of modified γ-cyclodextrins bearing two pyrene moieties [J].