Highly Stereospecific Generation of Helical Chirality by Imprinting with Amino Acids: A Universal Sensor for Amino Acid Enantiopurity

被引：89

作者：

Kim, Hyunwoo ^{[3
]}

So, Soon Mog ^{[3
]}

Yen, Cindy Pai-Hui ^{[3
]}

Vinhato, Elisangela ^{[3
]}

Lough, Alan J. ^{[3
]}

Hong, Jong-In ^{[1
]}

Kim, Hae-Jo ^{[2
]}

Chin, Jik ^{[3
]}

机构：

[1] Seoul Natl Univ, Dept Chem, Seoul 151747, South Korea

[2] Kyonggi Univ, Dept Chem, Suwon 443760, South Korea

[3] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 45期

基金：

加拿大自然科学与工程研究理事会;

关键词：

amino acids; chirality; circular dichroism; helical structures;

D O I：

10.1002/anie.200803116

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Helical chirality can be imprinted onto a 2,2′-dihydroxybenzophenone derivative (see picture) in a highly stereospecific manner. A single amino acid combines with the receptor to form an imine with two internal hydrogen bonds. The azo group allows sensing of amino acid enantiopurity by circular dichroism spectroscopy. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8657 / 8660

页数：4

共 36 条

[1]

Berova N., 2000, CIRCULAR DICHROISM P, P337

[2] Origin, control, and application of supramolecular chirogenesis in bisporphyrin-based systems [J].

Borovkov, VV ;

Hembury, GA ;

Inoue, Y .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :449-459

[3] Tertiary aromatic amide for memory of chirality:: Access to enantioenriched α-substituted valine [J].

Branca, Mathieu ;

Gori, Didier ;

Guilot, Regis ;

Alezra, Valerie ;

Kouklovsky, Cyrille .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (18) :5864-+

[4] Transfer of chiral information through molecular assembly [J].

Castellano, RK ;

Nuckolls, C ;

Rebek, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11156-11163

[5] Imprinting and locking chiral memory for stereoselective catalysis [J].

Chin, Jik ;

Chong, Yong S. ;

Bobb, Rhiana ;

Studnicki, Lisa ;

Hong, Jong-In .

CHEMICAL COMMUNICATIONS, 2007, (02) :120-122

[6]

Dunitz J. D., 2001, ANGEW CHEM, V113, P4295

[7]

Dunitz JD, 2001, ANGEW CHEM INT EDIT, V40, P4167, DOI 10.1002/1521-3773(20011119)40:22<4167::AID-ANIE4167>3.0.CO

[8]

2-Q

[9] The Bip method, based on the induced circular dichroism of a flexible biphenyl probe in terminally protected -Bip-Xaa*-dipeptides, for assignment of the absolute configuration of β-amino acids [J].

Dutot, Laurence ;

Wright, Karen ;

Gaucher, Anne ;

Wakselman, Michel ;

Mazaleyrat, Jean-Paul ;

De Zotti, Marta ;

Peggion, Cristina ;

Formaggio, Fernando ;

Toniolo, Claudio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (18) :5986-5992

[10] Macroscopic expression of the chirality of amino alcohols by a double amplification mechanism in liquid crystalline media [J].

Eelkema, R ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13480-13481

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