Synthesis of chiral 1,3-calix[4](crown-6) ethers as potential mediators for asymmetric recognition processes

被引:36
作者
Bitter, I [1 ]
Köszegi, É
Grün, A
Bakó, P
Pál, K
Grofcsik, A
Kubinyi, M
Balázs, B
Tóth, G
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Dept Phys Chem, H-1521 Budapest, Hungary
[3] Budapest Univ Technol & Econ, Hungarian Acad Sci, Inst Gen & Analyt Chem, Tech Analyt Res Grp, H-1521 Budapest, Hungary
[4] Hungarian Acad Sci, Chem Res Ctr, H-1525 Budapest, Hungary
基金
匈牙利科学研究基金会;
关键词
D O I
10.1016/S0957-4166(03)00174-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel chromogenic 1,3-calix[4](crown-6) derivatives comprised of 1,1'-binaphthyl-, methyl-alpha-D-glucoside-and D-mannitol moieties in the crown ether ring have been synthesized. UV-vis spectroscopic measurements of the 2,4-dinitrophenylazo chromogenic molecules indicated noticeable chiral discrimination associated with coloration towards primary amine enantiomers. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1025 / 1035
页数:11
相关论文
共 28 条
[1]  
Alberts B., 1983, MOL BIOL CELL
[2]   Novel monoaza- and diazacrown ethers incorporating sugar units and their extraction ability towards picrate salts [J].
Bako, P ;
Toke, L .
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1995, 23 (03) :195-201
[3]  
Balázs B, 2001, EUR J ORG CHEM, V2001, P61
[4]   Studies on calix(aza)crowns, III.: Synthesis of 1,3-alternate calix[4]arenes capped by diamide bridges [J].
Bitter, I ;
Grün, A ;
Balázs, B ;
Tóth, G ;
Horváth, G ;
Toke, L .
SYNTHETIC COMMUNICATIONS, 1999, 29 (22) :3905-3917
[5]   Novel chromogenic pyridinium derivatives of calix[4]arenes .2. [J].
Bitter, I ;
Grun, A ;
Toke, L ;
Toth, G ;
Balazs, B ;
MohammedZiegler, I ;
Grofcsik, A ;
Kubinyi, M .
TETRAHEDRON, 1997, 53 (49) :16867-16876
[6]   Novel chromogenic pyridinium derivatives of calix[4]arenes .1. [J].
Bitter, I ;
Grun, A ;
Toth, G ;
Szollosy, A ;
Horvath, G ;
Agai, B ;
Toke, L .
TETRAHEDRON, 1996, 52 (02) :639-646
[7]   Studies on calix(aza)crowns, .1. Synthesis, alkylation reactions and comprehensive NMR investigation of capped calix[4]arenes [J].
Bitter, I ;
Grun, A ;
Toth, G ;
Balazs, B ;
Toke, L .
TETRAHEDRON, 1997, 53 (28) :9799-9812
[8]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[9]   Charged cyclodextrin derivatives as chiral selectors in capillary electrophoresis [J].
Chankvetadze, B ;
Endresz, G ;
Blaschke, G .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :141-&
[10]   Synthesis and alkali cation extraction ability of 1,3-alt-thiacalix[4]mono(crown) ethers [J].
Csokai, V ;
Grün, A ;
Parlagh, G ;
Bitter, I .
TETRAHEDRON LETTERS, 2002, 43 (42) :7627-7629