Enantioselective analysis of an asymmetric reaction using a chiral fluorosensor

被引:69
作者
Tumambac, GE [1 ]
Wolf, C [1 ]
机构
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
关键词
D O I
10.1021/ol0516216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An axially chiral 1,8-dipyridylnaphthalene N,N'-dioxide has been employed in enantioselective fluorescence analysis of the enzymatic kinetic resolution of trans-1,2-diaminocyclohexane. The procedure eliminates cumbersome purification and derivatization steps required by traditional methods. The results demonstrate the potential of fluorescence spectroscopy using suitable chiral chemosensors for real-time analysis of the enantiomeric composition of chiral compounds and for high-throughput screening of asymmetric reactions.
引用
收藏
页码:4045 / 4048
页数:4
相关论文
共 38 条
[1]   EMDee: An enzymatic method for determining enantiomeric excess [J].
Abato, P ;
Seto, CT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9206-9207
[2]   Sequential biocatalytic resolution of (+/-)-trans-cyclohexane-1,2-diamine. Chemoenzymatic synthesis of an optically active polyamine [J].
Alfonso, I ;
Astorga, C ;
Rebolledo, F ;
Gotor, V .
CHEMICAL COMMUNICATIONS, 1996, (21) :2471-2472
[3]  
Alfonso I, 2000, CHEM-EUR J, V6, P3331, DOI 10.1002/1521-3765(20000915)6:18<3331::AID-CHEM3331>3.0.CO
[4]  
2-8
[5]   Chiral discrimination with a fluorescent boron-dipyrromethene dye [J].
Beer, G ;
Rurack, K ;
Daub, J .
CHEMICAL COMMUNICATIONS, 2001, (12) :1138-1139
[6]  
Ding KL, 1999, ANGEW CHEM INT EDIT, V38, P497, DOI 10.1002/(SICI)1521-3773(19990215)38:4<497::AID-ANIE497>3.0.CO
[7]  
2-G
[8]   Direct visual detection of the stereoselectivity of a catalytic reaction [J].
Eelkema, R ;
van Delden, RA ;
Feringa, BL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) :5013-5016
[9]   Isotopically chiral probes for in situ high-throughput asymmetric reaction analysis [J].
Evans, MA ;
Morken, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) :9020-9021
[10]  
Guo JH, 1999, ANGEW CHEM INT EDIT, V38, P1755, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1755::AID-ANIE1755>3.0.CO