Recognition of primary amines in water by a zinc funnel complex based on calix[6]arene

被引：37
作者：
Bistri, Olivia [1 ]
Colasson, Benoit [1 ]
Reinaud, Olivia [1 ]
机构：
[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, CNRS UMR 8601, PRES Sorbonne Paris Cite, F-75006 Paris, France
来源：
CHEMICAL SCIENCE | 2012年 / 3卷 / 03期
关键词：
HOST-GUEST COMPLEXATION; BOVINE SERUM-ALBUMIN; HYDROXO-CU(II) COMPLEXES; SUPRAMOLECULAR CHEMISTRY; SOLUBLE CALIXARENES; EFFICIENT SYNTHESIS; IONIC INTERACTIONS; NEUTRAL MOLECULES; TERMINAL ALKYNES; AQUEOUS-SOLUTION;
D O I：
10.1039/c1sc00738f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A water-soluble calix[6]arene-based tris(imidazole) ligand behaves as a highly selective receptor for primary amines in the presence of Zn(II) in water near physiological pH. It represents the first compound of this family of ligands that binds a Zn dication and an organic guest in water, thus giving rise to a stable host-guest adduct in spite of the highly competitive medium. The herein described self-assembly process displays a remarkable set of biomimetic properties. The ternary system (calix/Zn/amine) is formed in a very synergistic and allosteric manner and stabilizes the neutral form of the amino guest with a spectacular pseudo-pK(a) shift of ca. 7 units. This system constitutes an interesting structural model of metalloenzymes in aqueous solution.
引用
收藏
页码：811 / 818
页数：8
相关论文
共 75 条
[1]   Water-soluble pentasulfonatocalix[5]arene: selective recognition of ditopic trimethylammonium cations by a triple non-covalent interaction [J].
Arena, G ;
Gentile, S ;
Gulino, FG ;
Sciotto, D ;
Sgarlata, C .
TETRAHEDRON LETTERS, 2004, 45 (38) :7091-7094
[2]   DOUBLE PARTIAL CONE CONFORMATION FOR NA8(CALIX[6]ARENE SULFONATE).20 5H2O AND ITS PARENT ACID [J].
ATWOOD, JL ;
CLARK, DL ;
JUNEJA, RK ;
ORR, GW ;
ROBINSON, KD ;
VINCENT, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) :7558-7559
[3]  
Aubert-Foucher E., 1999, Fr. Pat., FR 60252J, Patent No. 60252
[4]   Dynamically self-assembling metalloenzyme models based on calixarenes [J].
Bakirci, Huseyin ;
Koner, Apurba L. ;
Dickman, Michael H. ;
Kortz, Ulrich ;
Nau, Werner M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (44) :7400-7404
[5]  
Bertini I., 1994, Bioinorganic Chemistry
[6]   Spontaneous formation of vesicles in a catanionic association involving a head and tail functionalized amino-calix[6]arene [J].
Bize, Cecile ;
Garrigues, Jean-Christophe ;
Blanzat, Muriel ;
Rico-Lattes, Isabelle ;
Bistri, Olivia ;
Colasson, Benoit ;
Reinaud, Olivia .
CHEMICAL COMMUNICATIONS, 2010, 46 (04) :586-588
[7]   A novel calix[6]arene-based mononuclear copper(I) complex that exhibits chirality at low temperature [J].
Blanchard, S ;
Rager, MN ;
Duprat, AF ;
Reinaud, O .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (11) :1143-1146
[8]  
Casnati A, 2001, CALIXARENES 2001, P440
[9]   Host properties of alpha-cyclodextrin and a water-soluble calix[6]arene probed with dimeric bipyridinium guests [J].
Castro, R ;
Godinez, LA ;
Criss, CM ;
Kaifer, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :4928-4935
[10]   Solid-state and solution complexation of cobalt(III) sepulchrate by a water-soluble calix[6]arene host [J].
Castro, R ;
Godinez, LA ;
Criss, CM ;
Bott, SG ;
Kaifer, AE .
CHEMICAL COMMUNICATIONS, 1997, (10) :935-936
12345678