Chiral binol-bisboronic acid as fluorescence sensor for sugar acids

被引:200
作者
Zhao, JZ
Fyles, TM
James, TD [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
[2] Univ Victoria, Dept Chem, Victoria, BC V8W 3V6, Canada
关键词
boronic acids; chiral recognition; fluorescence sensors; sugar acids; tartaric acid;
D O I
10.1002/anie.200454033
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel fluorescence response to enantiomeric analytes was observed for binol-bisboronic acid sensors (R- or S-1): One enantiomer of the analyte enhances and the other enantiomer diminishes the fluorescence of 1. So, the fluorescence intensity of R-1 was enhanced by D-tartaric acid and diminished by L-tartaric acid (see scheme). These changes are mirrored by the 5 sensor.
引用
收藏
页码:3461 / 3464
页数:4
相关论文
共 44 条
[1]   PHOTOPHYSICAL RECOGNITION OF CHIRAL SURFACES [J].
AVNIR, D ;
WELLNER, E ;
OTTOLENGHI, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2001-2003
[2]   Chiral discrimination with a fluorescent boron-dipyrromethene dye [J].
Beer, G ;
Rurack, K ;
Daub, J .
CHEMICAL COMMUNICATIONS, 2001, (12) :1138-1139
[3]   Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose [J].
Cao, HS ;
Diaz, DI ;
DiCesare, N ;
Lakowicz, JR ;
Heagy, MD .
ORGANIC LETTERS, 2002, 4 (09) :1503-1505
[4]   Modified BINOL ligands in asymmetric catalysis [J].
Chen, Y ;
Yekta, S ;
Yudin, AK .
CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211
[5]  
Davis A. P., 1999, ANGEW CHEM, V111, P3160
[6]   Signaling recognition events with fluorescent sensors and switches [J].
de Silva, AP ;
Gunaratne, HQN ;
Gunnlaugsson, T ;
Huxley, AJM ;
McCoy, CP ;
Rademacher, JT ;
Rice, TE .
CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566
[7]   A new highly fluorescent probe for monosaccharides based on a donor-acceptor diphenyloxazole [J].
DiCesare, N ;
Lakowicz, JR .
CHEMICAL COMMUNICATIONS, 2001, (19) :2022-2023
[8]   A new glucose-selective fluorescent bisboronic acid.: First report of strong α-furanose complexation in aqueous solution at physiological pH [J].
Eggert, H ;
Frederiksen, J ;
Morin, C ;
Norrild, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3846-3852
[9]   CHIRAL RECOGNITION OF TARTARIC ACID-DERIVATIVES BY A SYNTHETIC RECEPTOR [J].
GARCIATELLADO, F ;
ALBERT, J ;
HAMILTON, AD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (24) :1761-1763
[10]   Optically active dendrimers with a binaphthyl core and phenylene dendrons: Light harvesting and enantioselective fluorescent sensing [J].
Gong, LZ ;
Hu, QS ;
Pu, L .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2358-2367