Influence of the size and geometry of the anion binding pocket of sugar-urea anion receptors on chiral recognition

被引：25
作者：
Hamankiewicz, Paulina [1 ]
Granda, Jaroslaw M. [2 ]
Jurczak, Janusz [1 ,2 ]
机构：
[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 41期
关键词：
Anion binding; Chiral recognition; Monosaccharides; Urea; FLUORIDE-SELECTIVE FLUORESCENT; PROTONATION CONSTANTS; BUILDING-BLOCK; HYDROGEN; COMPLEXATION; EFFICIENT; DESIGN; NMR;
D O I：
10.1016/j.tetlet.2013.08.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new chiral urea-type anion receptors were synthesized from aromatic diamines and 1-amino-1-deoxyglucose. The anion binding properties of these receptors were studied using chiral carboxylates derived from mandelic acid and three a-amino acids. We found that the size of the anion binding pocket played an important role in chiral recognition processes. The best results were obtained for 1,8-diaminoanthracene and a-amino acid anions. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5608 / 5611
页数：4
相关论文
共 38 条
  • [1] Anion recognition by hydrogen bonding: urea-based receptors
    Amendola, Valeria
    Fabbrizzi, Luigi
    Mosca, Lorenzo
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3889 - 3915
  • [2] [Anonymous], ANGEW CHEM
  • [3] Avalos M, 2006, EUR J ORG CHEM, V2006, P657
  • [4] Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO
  • [5] 2-P
  • [6] Belen J. M., 2012, ORG BIOMOL CHEM, V10, P1181
  • [7] Carboxylate complexation by a family of easy-to-make ortho-phenylenediamine based bis-ureas:: studies in solution and the solid state
    Brooks, SJ
    Edwards, PR
    Gale, PA
    Light, ME
    [J]. NEW JOURNAL OF CHEMISTRY, 2006, 30 (01) : 65 - 70
  • [8] Carboxylate complexation by 1,1′-(1,2-phenylene)bis(3-phenylurea) in solution and the solid state
    Brooks, SJ
    Gale, PA
    Light, ME
    [J]. CHEMICAL COMMUNICATIONS, 2005, (37) : 4696 - 4698
  • [9] Anion receptor chemistry: highlights from 2007
    Caltagirone, Claudia
    Gale, Philip A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) : 520 - 563
  • [10] Fluoride detection based on fluorescence enhancement of thioureido naphthalene derivative
    Chakraborty, Sourav
    Tarr, Matthew A.
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2007, 85 (02): : 153 - 156
1234