Enantioselective fluorescent sensors for chiral carboxylates based on calix[4]arenes bearing an L-tryptophan unit

被引：67

作者：

Qing, Guang-yan ^{[1
]}

He, Yong-bing ^{[1
]}

Wang, Feng ^{[1
]}

Qin, Hai-juan ^{[1
]}

Hu, Chen-guang ^{[1
]}

Yang, Xi ^{[1
]}

机构：

[1] Wuhan Univ, Dept Chem, Wuhan 430072, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 11期

关键词：

calixarenes; tryptophan; fluorescence; enantioselective recognition; carboxylates; NMR spectroscopy;

D O I：

10.1002/ejoc.200600917

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two-armed chiral calix[4]arenes (3a-c) functionalized at the lower ring with L-tryptophan units have been prepared and the structures of these receptors characterized by IR, MS, H-1, and C-13 NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and H-1 NMR spectroscopy. The receptors exhibited different chiral recognition abilities towards some enantiomers of chiral materials and formed 1:1 complexes between host and guest. Receptor 3a exhibits excellent enantioselective fluorescent recognition ability towards the N-Boc-protected alanine anion and 3b reveals good enantioselective recognition ability towards the enantiomers of mandelate. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：1768 / 1778

页数：11

共 74 条

[71] Enantiomeric recognition of amine compounds by chiral macrocyclic receptors [J].

Zhang, XX ;

Bradshaw, JS ;

Izatt, RM .

CHEMICAL REVIEWS, 1997, 97 (08) :3313-3361

[72] An enantioselective fluorescent sensor for sugar acids [J].

Zhao, JZ ;

Davidson, MG ;

Mahon, MF ;

Kociok-Köhn, G ;

James, TD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) :16179-16186

[73] Chiral binol-bisboronic acid as fluorescence sensor for sugar acids [J].

Zhao, JZ ;

Fyles, TM ;

James, TD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3461-3464

[74] Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure (α,ß-amino alcohol groups [J].

Zheng, YS ;

Zhang, C .

ORGANIC LETTERS, 2004, 6 (08) :1189-1192

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