Enantioselective transport and liquid-liquid extraction of amino acids as their potassium and sodium salts by optically active diaza-18-crown-6 ethers

被引：18

作者：

Demirel, N ^{[1
]}

Bulut, Y ^{[1
]}

Hosgören, H ^{[1
]}

机构：

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

来源：

CHIRALITY | 2004年 / 16卷 / 06期

关键词：

crown compounds; transport of amino acids; molecular recognition; supramolecular chemistry; host-guest systems;

D O I：

10.1002/chir.20046

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Complexation of amino acids as their sodium and potassium salts by optically active diaza crown ethers has been investigated in transport across bulk liquid membranes containing the carriers and in extraction experiments. The observed enantio selectivity was achieved by (noncovalent) steric and repulsive interactions between the side arm of the crown ether and functional group(s) of the amino acids. The highest enantio selectivity was observed in the case of tryptophan. (C) 2004 Wiley-Liss, Inc.

引用

页码：347 / 350

页数：4

共 13 条

[1] Guanidinium receptors as enantioselective amino acid membrane carriers
Breccia, P
Van Gool, M
Pérez-Fernández, R
Martín-Santamaría, S
Gago, F
Prados, P
de Mendoza, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) : 8270 - 8284
[2] CHIRAL DIAZA-18-CROWN-6 DERIVATIVES
CHADWICK, DJ
CLIFFE, IA
SUTHERLAND, IO
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (19) : 992 - 994
[3] Christiansen N. H., 1962, AMINO ACID POOLS, P527
[4] Demirel N, 2003, J CHEM RES, P610
[5] GOKEL GW, 1991, MONOGRAPHS SUPRAMOLE
[6] Easy synthesis of a new C-2-symmetric diaza-crown ether from L-threonine
Joly, JP
Schroder, G
[J]. TETRAHEDRON LETTERS, 1997, 38 (47) : 8197 - 8198
[7] LEHN JM, 1993, CHEM SUPRAMOLEKURNA
[8] MYAKE H, 1994, TETRAHEDRON LETT, V35, P681
[9] Chiral discrimination of amino acids and their potassium or sodium salts by optically active crown ether derived from D-mannose
Pietraszkiewicz, M
Kozbial, M
Pietraszkiewicz, O
[J]. JOURNAL OF MEMBRANE SCIENCE, 1998, 138 (01) : 109 - 113
[10] SEEL C, 1995, TOP CURR CHEM, V175, P101

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