An enantioselective fluorescent sensor for sugar acids

被引:173
作者
Zhao, JZ
Davidson, MG
Mahon, MF
Kociok-Köhn, G
James, TD [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
[2] Univ Bath, Bath Chem Crystallog, Bath BA2 7AY, Avon, England
关键词
D O I
10.1021/ja046289s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral fluorescent boronic acid 1 was found to be a highly enantioselective, chemoselective, and sensitive sensor for sugar acids, such as tartaric acid. Enantioselectivities (K-R/K-S) of up to 550:1, chemoselectivity up to 11000:1, and sensitivities in the micromolar range with sensor 1 were observed. Single-crystal X-ray analysis was used to confirm the structure of the fluorescent species.
引用
收藏
页码:16179 / 16186
页数:8
相关论文
共 27 条
[1]   Probing disaccharide selectivity with modular fluorescent sensors [J].
Arimori, S ;
Phillips, MD ;
James, TD .
TETRAHEDRON LETTERS, 2004, 45 (07) :1539-1542
[2]   Tuning saccharide selectivity in modular fluorescent sensors [J].
Arimori, S ;
Consiglio, GA ;
Phillips, MD ;
James, TD .
TETRAHEDRON LETTERS, 2003, 44 (25) :4789-4792
[3]   A modular electrochemical sensor for saccharides [J].
Arimori, S ;
Ushiroda, S ;
Peter, LM ;
Jenkins, ATA ;
James, TD .
CHEMICAL COMMUNICATIONS, 2002, (20) :2368-2369
[4]   A modular fluorescence intramolecular energy transfer saccharide sensor [J].
Arimori, S ;
Bell, ML ;
Oh, CS ;
James, TD .
ORGANIC LETTERS, 2002, 4 (24) :4249-4251
[5]   Modular fluorescence sensors for saccharides [J].
Arimori, S ;
Bell, ML ;
Oh, CS ;
Frimat, KA ;
James, TD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (06) :803-808
[6]  
Arimori S, 2001, CHEM COMMUN, P1836, DOI 10.1039/b105994g
[7]   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
[8]   Study of the mechanism of electron-transfer quenching by boron-nitrogen adducts in fluorescent sensors [J].
Franzen, S ;
Ni, WJ ;
Wang, BH .
JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (47) :12942-12948
[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]   Recognition of insoluble tartaric acid in chloroform [J].
Goswami, S ;
Ghosh, K ;
Mukherjee, R .
TETRAHEDRON, 2001, 57 (23) :4987-4993