Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes

被引：18

作者：

Bois, Joackim ^{[1
,2
]}

Bonnamour, Isabelle ^{[1
,2
]}

Duchamp, Christian ^{[1
,2
]}

Parrot-Lopez, Helene ^{[1
,2
]}

Darbost, Ulrich ^{[1
,2
]}

Felix, Caroline ^{[1
,2
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5246, Inst Chim & Biochim Mol & Supramol,CSAp, F-69622 Villeurbanne, France

[2] Univ Lyon, Lyon, France

来源：

NEW JOURNAL OF CHEMISTRY | 2009年 / 33卷 / 10期

关键词：

ELECTROSPRAY MASS-SPECTROMETRY; ENANTIOMERIC RECOGNITION; OPTICALLY PURE; DERIVATIVES; BEARING; RECEPTORS; PHENYLALANINE; COMPLEXATION; TRYPTOPHAN; PHASE;

D O I：

10.1039/b907190c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In order to prepare new molecular hosts able to discriminate enantiomers of amino-acid derivatives, we have synthesized chiral thiacalix[4]arenes. Extensive studies using NMR and mass spectrometry techniques allow us to determine the major supramolecular interactions involved in the recognition process. Moreover, a titration study enables us to determine the binding constant between these new hosts and a series of amino-acid derivatives. Finally, we have also demonstrated that these calixarenes are able to discriminate enantiomers of amino-acid guests.

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收藏

页码：2128 / 2135

页数：8

相关论文

共 45 条

[1] Chiral recognition in gas-phase cyclodextrin: Amino acid complexes - Is the three point interaction still valid in the gas phase? [J].

Ahn, S ;

Ramirez, J ;

Grigorean, G ;

Lebrilla, CB .

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2001, 12 (03) :278-287

[2] Synthesis and structure of lower rim C-linked tetra-N-tosyl peptidocalix[4]arenes [J].

Ben Sdira, S ;

Baudry, R ;

Felix, CP ;

Giudicelli, MBA ;

Lamartine, RJ .

TETRAHEDRON LETTERS, 2004, 45 (41) :7801-7804

[3] Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]arenes [J].

Ben Sdira, S ;

Felix, CP ;

Giudicelli, MBA ;

Seigle-Ferrand, PF ;

Perrin, M ;

Lamartine, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6632-6638

[4] A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].

BENESI, HA ;

HILDEBRAND, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707

[5] Upper rim appended hybrid calixarenes via click chemistry [J].

Bew, Sean P. ;

Brimage, Rebecca A. ;

L'Hermite, Nathalie ;

Sharma, Sunil V. .

ORGANIC LETTERS, 2007, 9 (19) :3713-3716

[6] Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines [J].

Botta, Bruno ;

D'Acquarica, Ilaria ;

Nevola, Laura ;

Sacco, Fabiola ;

Lopez, Zara Valbuena ;

Zappia, Giovanni ;

Fraschetti, Caterina ;

Speranza, Maurizio ;

Tafi, Andrea ;

Caporuscio, Fabiana ;

Letzel, Matthias C. ;

Mattay, Jochen .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :5995-6002

[7] Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids [J].

Bozkurt, Selahattin ;

Durmaz, Mustafa ;

Yilmaz, Mustafa ;

Sirit, Abdulkadir .

TETRAHEDRON-ASYMMETRY, 2008, 19 (05) :618-623

[8] The use of electrospray mass spectrometry (ES/MS) for the differential detection of some steroids as calix-[n]-arene sulphonate complexes [J].

Da Silva, E ;

Valmalle, C ;

Becchi, M ;

Cuilleron, CY ;

Coleman, AW .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2003, 46 (1-2) :65-69

[9] Optically pure calix[6]tris-ammoniums: Syntheses and host-guest properties toward neutral guests [J].

Darbost, U ;

Zeng, XS ;

Giorgi, M ;

Jabin, I .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) :10552-10560

[10] Enantiomeric recognition of amino acid derivatives by chiral Schiff bases of calix[4]arene [J].

Durmaz, Mustafa ;

Alpaydin, Sabri ;

Sirit, Abdulkadir ;

Yilmaz, Mustafa .

TETRAHEDRON-ASYMMETRY, 2007, 18 (07) :900-905

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