Enantioselective recognition of a chiral quaternary ammonium ion by C3 symmetric cyclic hexapeptides

被引:33
作者
Heinrichs, G
Vial, L
Lacour, J
Kubik, S [1 ]
机构
[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany
[2] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
关键词
D O I
10.1039/b302092d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C-3 Symmetric cyclic hexapeptides containing alternating L-proline and 3-aminobenzoic acid derivatives as subunits possess different affinities towards the two enantiomers of the N,N,N-trimethyl-1-phenylethyl ammonium cation.
引用
收藏
页码:1252 / 1253
页数:2
相关论文
共 17 条
[1]   Benzimidazole receptors for carboxylic acids [J].
Almaraz, M ;
Martín, M ;
Hernández, JV ;
Caballero, MC ;
Morán, JR .
TETRAHEDRON LETTERS, 1998, 39 (13) :1811-1814
[2]   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
[3]   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
[4]  
Connors K. A, 1987, BINDING CONSTANTS ME
[5]   Determination of association constants (Ka) from solution NMR data [J].
Fielding, L .
TETRAHEDRON, 2000, 56 (34) :6151-6170
[6]   Syntheses of chiral homoazacalix[4]arenes incorporating amino acid residues: Molecular recognition for racemic quaternary ammonium ions [J].
Ito, K ;
Noike, M ;
Kida, A ;
Ohba, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7519-7522
[7]   Syntheses of chiral bishomodiazacalix[4]arenes incorporating amino acid residues: Molecular recognition for racemic ammonium ions by the macrocycles possessing tyrosine residues [J].
Ito, K ;
Ohta, T ;
Ohba, Y ;
Sone, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (01) :79-85
[8]  
IZATT RM, 1992, CROWN ETHERS FUTURE, P207
[9]   Unprecedented chiral molecular recognition in a C3-symmetric environment [J].
Kim, SG ;
Kim, KH ;
Jung, J ;
Shin, SK ;
Ahn, KH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (04) :591-596
[10]   A new cyclic pseudopeptide composed of (L)-proline and 3-aminobenzoic acid subunits as a ditopic receptor for the simultaneous complexation of cations and anions [J].
Kubik, S ;
Goddard, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9475-9486