Enantioselective CD analysis of amino acids based on chiral amplification with a stereodynamic probe

被引：26

作者：

Ghosn, Marwan W. ^{[1
]}

Wolf, Christian ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 23期

关键词：

Amino acids; Sensing; Chiral amplification; Circular dichroism; Dynamic stereochemistry; INDICATOR DISPLACEMENT ASSAYS; INDUCED AXIAL CHIRALITY; ENANTIOMERIC EXCESS; FLUORESCENT RECOGNITION; ABSOLUTE-CONFIGURATION; COPPER(II) COMPLEX; CIRCULAR-DICHROISM; CARBOXYLIC-ACIDS; BIPHENYL CORE; RESIDUE BIP;

D O I：

10.1016/j.tet.2010.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation between stereolabile 1,8-bis(3'-formy1-4'-hydroxyphenyl)naphthalene, 1, and two amino acid molecules results in the formation of chiral diimines exhibiting strong CD signals. This reaction has been used to develop a chiroptical sensing method for the determination of the absolute configuration and enantiomeric composition of unprotected amino acids. This sensing approach is based on distinctive chiral amplification due to central-to-axial chirality induction within the diimine scaffold formed and does not require the use of an enantiopure ligand or metal complex. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3989 / 3994

页数：6

共 46 条

[11] Highly enantioselective fluorescent sensor for chiral recognition of amino acid derivatives [J].

He, Xuan ;

Cui, Xin ;

Li, Maosi ;

Lin, Lili ;

Liu, Xiaohua ;

Feng, Xiaoming .

TETRAHEDRON LETTERS, 2009, 50 (42) :5853-5856

[12] Antibodies can recognize the chiral center of free α-amino acids [J].

Hofstetter, O ;

Hofstetter, H ;

Schurig, V ;

Wilchek, M ;

Green, BS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3251-3252

[13] Synthesis and circular dichroism studies of N,N-bis(2-quinolylmethyl)amino acid Cu(II) complexes: Determination of absolute configuration and enantiomeric excess by the exciton coupling method [J].

Holmes, AE ;

Zahn, S ;

Canary, JW .

CHIRALITY, 2002, 14 (06) :471-477

[14] SYNTHESIS OF SOME DIPHENYL AND TRIPHENYL DERIVATIVES OF ANTHRACENE AND NAPHTHALENE [J].

HOUSE, HO ;

CAMPBELL, WJ ;

KOEPSELL, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :1003-&

[15] Synthesis of new chiral crown ethers containing a (p-methoxyphenoxy)methyl moiety and their chiral recognition ability towards amino acid esters [J].

Karakaplan, M ;

Aral, T .

TETRAHEDRON-ASYMMETRY, 2005, 16 (12) :2119-2124

[16] Highly Stereospecific Generation of Helical Chirality by Imprinting with Amino Acids: A Universal Sensor for Amino Acid Enantiopurity [J].

Kim, Hyunwoo ;

So, Soon Mog ;

Yen, Cindy Pai-Hui ;

Vinhato, Elisangela ;

Lough, Alan J. ;

Hong, Jong-In ;

Kim, Hae-Jo ;

Chin, Jik .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8657-8660

[17] Large chiral discrimination of a molecular probe by bovine serum albumin [J].

Kumar, CV ;

Buranaprapuk, A ;

Sze, HC .

CHEMICAL COMMUNICATIONS, 2001, (03) :297-298

[18]

LEACH BE, 1971, J AM CHEM SOC, V93, P3377

[19] Using enantioselective indicator displacement assays to determine the enantiomeric excess of α-amino acids [J].

Leung, Diana ;

Folmer-Andersen, J. Frantz ;

Lynch, Vincent M. ;

Anslyn, Eric V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12318-12327

[20] Transitioning enantioselective indicator displacement assays for α-amino acids to protocols amenable to high-throughput screening [J].

Leung, Diana ;

Anslyn, Eric V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12328-12333

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