Synthesis of chiral diaza 18-crown-6 ethers from chiral amines and molecular recognition of potassium and sodium salts of amino acids

被引：27

作者：

Demirel, N ^{[1
]}

Bulut, Y ^{[1
]}

机构：

[1] Univ Dicle, Fac Sci, Dept Chem, TR-21280 Diyarbakir, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(03)00594-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A practical synthesis of chiral amine precursors 3 and 4 and chiral diaza 18-crown-6 ethers 5. 6 and 7 starting from chiral amines are reported. The molecular recognition of these chiral crown ethers for amino acids potassium and sodium salts has been characterized by UV-vis. The selectivity order is Phe>Thr>Ala. In the case of 6 the cavity of the macrocycle plays ail important role in recognition. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：2633 / 2637

页数：5

共 20 条

[1] MOLECULAR RECOGNITION .9. SIMULTANEOUS HYDROGEN-BONDING AND METAL COORDINATION INTERACTIONS IN THE 2-POINT FIXATION OF AMINO-ACIDS WITH A BIFUNCTIONAL METALLOPORPHYRIN RECEPTOR [J].

AOYAMA, Y ;

ASAKAWA, M ;

YAMAGISHI, A ;

TOI, H ;

OGOSHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3145-3151

[2] 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

[3] Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties [J].

Chen, X ;

Du, DM ;

Hua, WT .

TETRAHEDRON-ASYMMETRY, 2003, 14 (08) :999-1007

[4]

Connors K. A., 1987, BINDING CONSTANTS ME

[5]

DEMIREL N, 1999, THESIS DIYARBAKIR TU

[6] SOLUTION THERMODYNAMICS OF AMINO ACID-18 CROWN-6 AND AMINO ACID-CRYPTAND-222 COMPLEXATION REACTIONS [J].

DENAMOR, AFD ;

RITT, MC ;

LEWIS, DFV ;

SCHWINGWEILL, MJ ;

NEU, FA .

PURE AND APPLIED CHEMISTRY, 1991, 63 (10) :1435-1439

[7] CHIRAL RECOGNITION OF AROMATIC CARBOXYLATE ANIONS BY AN OPTICALLY-ACTIVE ABIOTIC RECEPTOR CONTAINING A RIGID GUANIDINIUM BINDING SUBUNIT [J].

ECHAVARREN, A ;

GALAN, A ;

LEHN, JM ;

DEMENDOZA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4994-4995

[8] Synthetic receptors [J].

Hartley, JH ;

James, TD ;

Ward, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3155-3184

[9] PERSPECTIVES IN SUPRAMOLECULAR CHEMISTRY - FROM MOLECULAR RECOGNITION TOWARDS MOLECULAR INFORMATION-PROCESSING AND SELF-ORGANIZATION [J].

LEHN, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (11) :1304-1319

[10] HOST-GUEST COMPLEXATION .22. RECIPROCAL CHIRAL RECOGNITION BETWEEN AMINO-ACIDS AND DILOCULAR SYSTEMS [J].

PEACOCK, SS ;

WALBA, DM ;

GAETA, FCA ;

HELGESON, RC ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2043-2052

← 1 2 →