Fluorous-Phase-Based Chiral Assay with Circular Dichroism Spectroscopy

被引：7

作者：

Xiao, Meng ^{[1
]}

Yu, Shanshan ^{[1
]}

Chen, Liming ^{[1
]}

Huang, Zeng ^{[1
]}

Wen, Kaili ^{[1
]}

Xu, Yimang ^{[1
]}

Zhao, Feng ^{[1
]}

Yu, Xiaoqi ^{[1
]}

Pu, Lin ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Univ Virginia, Dept Chem, Mccormick Rd, Charlottesville, VA 22904 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 11期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

Analytical methods; Sensors; Perfluorinated solvents; Circular dichroism; Chirality; ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; STEREODYNAMIC PROBES; ORGANIC-COMPOUNDS; CARBOXYLIC-ACIDS; AMINO-ACIDS; FLUORESCENCE; CHROMOPHORES; RECOGNITION; ASSIGNMENT;

D O I：

10.1002/ejoc.201601643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly fluorinated molecular probe made of a salicylaldehyde derivative is designed and synthesized for the detection of chiral amines in the fluorous phase. When treated with various chiral amines in a fluorous solvent (perfluorohexyl ethanol), this probe shows intense CD signals at wavelengths greater than 400 nm, which has been used to determine the enantiomeric composition of chiral amines, amino alcohols, and amino acids. This is the first example of CD recognition of chiral compounds that is conducted in the fluorous phase. The approach could greatly reduce the undesired interference in the direct assay of asymmetric reactions and catalytic processes.

引用

页码：1413 / 1417

页数：5

共 36 条

[1]

Aaron, 2014, J MED CHEM, V57, P3283

[2]

[Anonymous], 2007, ANGEW CHEM

[3]

Bakkari M. E., 2006, J FLUORINE CHEM, V127, P558

[4]

Balckari M. E., 2008, NEW J CHEM, V32, P193, DOI DOI 10.1039/B716544G

[5] 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

[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] Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].

Berova, Nina ;

Di Bari, Lorenzo ;

Pescitelli, Gennaro .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931

[8] Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts [J].

Berova, Nina ;

Pescitelli, Gennaro ;

Petrovic, Ana G. ;

Proni, Gloria .

CHEMICAL COMMUNICATIONS, 2009, (40) :5958-5980

[9] CD EXCITON CHIRALITY METHOD - NEW RED-SHIFTED CHROMOPHORES FOR HYDROXYL-GROUPS [J].

CAI, GL ;

BOZHKOVA, N ;

ODINGO, J ;

BEROVA, N ;

NAKANISHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7192-7198

[10]

Curran D., 2004, HDB FLUOROUS CHEM

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