Quantitative chirality sensing of amines and amino alcohols via Schiff base formation with a stereodynamic UV/CD probe

被引:34
作者
De los Santos, Zeus A. [1 ]
Ding, Ransheng [1 ]
Wolf, Christian [1 ]
机构
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
基金
美国国家科学基金会;
关键词
CIRCULAR-DICHROISM SPECTROSCOPY; ENANTIOMERIC EXCESS; RAPID-DETERMINATION; SIMULTANEOUSLY DETERMINE; FLUORESCENT SENSOR; CARBOXYLIC-ACIDS; SUBSTRATE; COMPLEXES; IDENTITY; CHEMOSENSOR;
D O I
10.1039/c5ob02529j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereodynamic chemosensor that can be used for simultaneous determination of the absolute configuration, enantiomeric composition and total concentration of chiral amines and amino alcohols based on two fast optical measurements was prepared and tested. The free sensor is CD-silent and produces characteristic blue-shifted UV and CD signals upon substrate binding via Schiff base formation. The potential in high-throughput screening applications and for rational sensor developments are discussed.
引用
收藏
页码:1934 / 1939
页数:6
相关论文
共 46 条
[1]   Advances in enantiomeric resolution on monolithic chiral stationary phases in liquid chromatography and electrochromatography [J].
Al-Othman, Zeid A. ;
Al-Warthan, Abdulrahman ;
Ali, Imran .
JOURNAL OF SEPARATION SCIENCE, 2014, 37 (9-10) :1033-1057
[2]   Rapid determination of enantiomeric excess of α-chiral aldehydes using circular dichroism spectroscopy [J].
Barman, Sanmitra ;
Anslyn, Eric V. .
TETRAHEDRON, 2014, 70 (06) :1357-1362
[3]   Chirality Sensing With Stereodynamic Biphenolate Zinc Complexes [J].
Bentley, Keith W. ;
de los Santos, Zeus A. ;
Weiss, Mary J. ;
Wolf, Christian .
CHIRALITY, 2015, 27 (10) :700-707
[4]   Comprehensive Chirality Sensing: Development of Stereodynamic Probes with a Dual (Chir)optical Response [J].
Bentley, Keith W. ;
Wolf, Christian .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) :6517-6531
[5]   Chirality Sensing of Amines, Diamines, Amino Acids, Amino Alcohols, and α-Hydroxy Acids with a Single Probe [J].
Bentley, Keith W. ;
Nam, Yea G. ;
Murphy, Jaslynn M. ;
Wolf, Christian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (48) :18052-18055
[6]   Stereodynamic Chemosensor with Selective Circular Dichroism and Fluorescence Readout for in Situ Determination of Absolute Configuration, Enantiomeric Excess, and Concentration of Chiral Compounds [J].
Bentley, Keith W. ;
Wolf, Christian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (33) :12200-12203
[7]   Optical chirality sensing using macrocycles, synthetic and supramolecular oligomers/polymers, and nanoparticle based sensors [J].
Chen, Zhan ;
Wang, Qian ;
Wu, Xin ;
Li, Zhao ;
Jiang, Yun-Bao .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (13) :4249-4263
[8]   In Situ Assembly of Octahedral Fe(II) Complexes for the Enantiomeric Excess Determination of Chiral Amines Using Circular Dichroism Spectroscopy [J].
Dragna, Justin M. ;
Pescitelli, Gennaro ;
Tran, Lee ;
Lynch, Vincent M. ;
Anslyn, Eric V. ;
Di Bari, Lorenzo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (09) :4398-4407
[9]   One-pot multi-substrate enantioselective conjugate addition of diethylzinc to nitroalkenes [J].
Duursma, A ;
Minnaard, AJ ;
Feringa, BL .
TETRAHEDRON, 2002, 58 (29) :5773-5778
[10]  
Gao X, 1998, CHIRALITY, V10, P120, DOI 10.1002/(SICI)1520-636X(1998)10:1/2<120::AID-CHIR19>3.0.CO