Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives

被引：53

作者：

Demirtas, Havva Nur ^{[1
]}

Bozkurt, Selahattin ^{[1
]}

Durmaz, Mustafa ^{[1
]}

Yilmaz, Mustafa ^{[1
]}

Sirit, Abdulkadir ^{[1
]}

机构：

[1] Selcuk Univ, Dept Chem, TR-42099 Konya, Turkey

来源：

TETRAHEDRON | 2009年 / 65卷 / 15期

关键词：

CATION-PI INTERACTIONS; ALKALI-METAL IONS; MOLECULAR RECOGNITION; DIAMIDE DERIVATIVES; SYNTHETIC RECEPTORS; CARBOXYLIC-ACIDS; COMPLEXATION; CALIXARENES; 2,4,6-TRIAMINOPYRIMIDINE; CONFORMATION;

D O I：

10.1016/j.tet.2009.01.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

in this study the synthesis of novel chiral calix[4]azacrown derivatives has been reported. The enantioselectivity of Chiral receptors was investigated by using UV-vis spectroscopy. All the chiral calix[4]arene derivative,; exhibited certain chiral recognition toward the enantiomers of phenylalanine (Phe-OMe.HCl) and alanine methyl ester hydrochlorides (Ala-OME.HCl). As a chiral receptor, the furfuryl-armed calix[4]azacrown ether 7 has the best enantiomeric discriminating ability for alpha-amino acid ester hydrochlorides (up to K-L/K-D 2.08, Delta Delta G(0) 1.82 KJ mol (1)) in CHCl3. The enantiomeric recognition abilities for 1,guests are also discussed from a thermodynamic point of view. (C) 2009 Elsevier Ltd. All rights reserved.

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页码：3014 / 3018

页数：5

相关论文

共 46 条

[1] Cation-pi interactions between neutral calix[5]arene hosts and cationic organic guests [J].

Arnecke, R ;

Bohmer, V ;

Cacciapaglia, R ;

Cort, AD ;

Mandolini, L .

TETRAHEDRON, 1997, 53 (13) :4901-4908

[2] Calix[4]azacrown and 4-aminophthalimide-appended calix[4]azacrown: synthesis, structure, complexation and fluorescence signaling behaviour [J].

Banthia, S ;

Samanta, A .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (08) :1428-1434

[3]

Beddell C. R., 1992, DESIGN DRUGS MACROMO

[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] Molecular recognition-induced function and competitive replacement by hydrogen-bonding interactions:: Amphiphilic barbituric acid derivatives, 2,4,6-triaminopyrimidine, and related structures at the air-water interface [J].

Bohanon, TM ;

Caruso, PL ;

Denzinger, S ;

Fink, R ;

Möbius, D ;

Paulus, W ;

Preece, JA ;

Ringsdorf, H ;

Schollmeyer, D .

LANGMUIR, 1999, 15 (01) :174-184

[6] CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].

BOHMER, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745

[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] Peptido- and glycocalixarenes: Playing with hydrogen bonds around hydrophobic cavities [J].

Casnati, A ;

Sansone, F ;

Ungaro, R .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :246-254

[9]

de Namor AFD, 1998, CHEM REV, V98, P2495

[10] Synthesis of new chiral calix[4]azacrowns for enantiomeric recognition of carboxylic acids [J].

Demirtas, Havva Nur ;

Bozkurt, Selahattin ;

Durmaz, Mustafa ;

Yilmaz, Mustafa ;

Sirit, Abdulkadir .

TETRAHEDRON-ASYMMETRY, 2008, 19 (17) :2020-2025

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