Guidelines in implementing enantioselective indicator-displacement assays for α-hydroxycarboxylates and diols

被引:179
作者
Zhu, L [1 ]
Zhong, ZL [1 ]
Anslyn, EV [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1021/ja0435945
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective association events between boronic acid receptors and bifunctional substrates such as alpha-hydroxycarboxylates and vicinal diols were exploited to develop enantioselective indicator-displacement assays. It was found that the sensitivity of the assay could be tuned by using either colorimetric or fluorescent indicators. Mathematical principles were established for concurrent determination of concentration and enantiomeric excess (ee) of a chiral analyte, which has been a challenge to the high-throughput analysis of chiral samples. Furthermore, experimental protocols were optimized to maximize the chiral resolution of the assay and to improve the accuracy of the ee measurements.
引用
收藏
页码:4260 / 4269
页数:10
相关论文
共 69 条
[1]  
Acton FS., 1970, NUMERICAL METHODS WO
[2]   Achieving large color changes in response to the presence of amino acids:: A molecular sensing ensemble with selectivity for aspartate [J].
Aït-Haddou, H ;
Wiskur, SL ;
Lynch, VM ;
Anslyn, EV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11296-11297
[3]   Chiral discrimination with a fluorescent boron-dipyrromethene dye [J].
Beer, G ;
Rurack, K ;
Daub, J .
CHEMICAL COMMUNICATIONS, 2001, (12) :1138-1139
[4]  
BIOOCCHI M, 2004, ANGEW CHEM, V43, P3847
[5]   A REAGENT FOR DETERMINING OPTICAL PURITIES OF DIOLS BY FORMATION OF DIASTEREOMERIC ARYLBORONATE ESTERS [J].
BURGESS, K ;
PORTE, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (11) :1182-1184
[6]   A competition assay for determining glucose-6-phosphate concentration with a tris-boronic acid receptor [J].
Cabell, LA ;
Monahan, MK ;
Anslyn, EV .
TETRAHEDRON LETTERS, 1999, 40 (44) :7753-7756
[7]   (S)-(+)-N-acetylphenylglycineboronic acid:: A chiral derivatizing agent for Ee determination of 1,2-diols [J].
Caselli, E ;
Danieli, C ;
Morandi, S ;
Bonfiglio, B ;
Forni, A ;
Prati, F .
ORGANIC LETTERS, 2003, 5 (25) :4863-4866
[8]   Measurement of enantiomeric excess using molecularly imprinted polymers [J].
Chen, YZ ;
Shimizu, KD .
ORGANIC LETTERS, 2002, 4 (17) :2937-2940
[9]  
Connors K. A., 1987, BINDING CONSTANTS ME
[10]   CHEMICAL COMMUNICATION IN WATER USING FLUORESCENT CHEMOSENSORS [J].
CZARNIK, AW .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) :302-308