Matched/mismatched interaction of a cyclic hexapeptide with ion pairs containing chiral cations and chiral anions

被引:31
作者
Heinrichs, G
Kubik, S
Lacour, J
Vial, L
机构
[1] Tech Univ Kaiserslauten, Fachbereich Chem Organ Chem, D-67663 Kaiserslautern, Germany
[2] Univ Geneva, Dept Chim Organ, CH-1211 Geneva, Switzerland
关键词
D O I
10.1021/jo050215x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The binding of a chiral quaternary ammonium ion to a cyclopeptide containing aromatic amino acid subunits is affected not only by the configuration of the cation but also by the configuration of the chiral counterion. Analysis of the binding equilibria shows that complex formation involves interaction of the whole ion pair with the host indicating that steric requirements of the anion influence complex geometry and stability.
引用
收藏
页码:4498 / 4501
页数:4
相关论文
共 30 条
[1]   Anion allosteric effect in the recognition of tetramethylammonium salts by calix[4]arene cone conformers [J].
Arduini, A ;
Giorgi, G ;
Pochini, A ;
Secchi, A ;
Ugozzoli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8302-8308
[2]  
Arduini A, 2000, EUR J ORG CHEM, V2000, P2325
[3]   Rigid cone calix[4]arenes as pi-donor systems: Complexation of organic molecules and ammonium ions in organic media [J].
Arduini, A ;
McGregor, WM ;
Paganuzzi, D ;
Pochini, A ;
Secchi, A ;
Ugozzoli, F ;
Ungaro, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (05) :839-846
[4]   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
[5]   Binding of acetylcholine and tetramethylammonium to a cyclophane receptor:: Anion's contribution to the cation-π interaction [J].
Bartoli, S ;
Roelens, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8307-8315
[6]   Electrostatic attraction of counterion dominates the cation-π interaction of acetylcholine and tetramethylammonium with aromatics in chloroform [J].
Bartoli, S ;
Roelens, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) :11908-11909
[7]   Counteranion effect on complexation of quats by a neutral calix[5]arene receptor [J].
Böhmer, V ;
Dalla Cort, A ;
Mandolini, L .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1900-1902
[8]  
Connors K. A, 1987, BINDING CONSTANTS ME
[9]   DOUBLY BRIDGED TETRAHOMODIOXACALIX[4]ARENES - SYNTHESIS AND COMPLEXATION OF QUATERNARY AMMONIUM-IONS [J].
DEIASI, G ;
MASCI, B .
TETRAHEDRON LETTERS, 1993, 34 (41) :6635-6638
[10]  
FRVARGER F, 2004, J ORG CHEM, V69, P8521