Chiral recognition with a benzofuran receptor that mimics an oxyanion hole

被引:13
|
作者
Fuentes de Arriba, Angel L. [1 ]
Gomez Herrero, Angel [1 ]
Rubio, Omayra H. [1 ]
Monleon, Laura M. [1 ]
Simon Rubio, Luis [1 ]
Alcazar, Victoria [2 ]
Sanz, Francisca [3 ]
Moran, Joaquin R. [1 ]
机构
[1] Univ Salamanca, Dept Organ Chem, E-37008 Salamanca, Spain
[2] Tech Univ Madrid, Ind Chem & Environm Engn Dept, Madrid 28006, Spain
[3] Univ Salamanca, Xray Diffract Serv, E-37008 Salamanca, Spain
关键词
NUCLEOPHILIC-ADDITION; ARTIFICIAL ENZYMES; ACID RECEPTORS; CATALYSIS; PYRROLIDINE; DESIGN;
D O I
10.1039/c4ob01954g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new chiral benzofuran receptor has been synthesized and its properties in the association of amino acid derivatives have been studied. X-ray structures were obtained and these corroborate the presence of an oxyanion-hole motif in these structures.
引用
收藏
页码:493 / 501
页数:9
相关论文
共 50 条
  • [1] Molecular recognition and catalysis: incorporation of an oxyanion hole into a synthetic receptor
    Fan, E.
    Vicent, C.
    Hamilton, A. D.
    New Journal of Chemistry, 21 (01):
  • [2] Molecular recognition and catalysis: Incorporation of an ''oxyanion hole'' into a synthetic receptor
    Fan, EK
    Vicent, C
    Hamilton, AD
    NEW JOURNAL OF CHEMISTRY, 1997, 21 (01) : 81 - 85
  • [3] Xanthone receptors as oxyanion-hole mimics in artificial enzymes
    Simón, L
    Muñiz, FM
    Sáez, S
    Raposo, C
    Sanz, F
    Morán, JR
    HELVETICA CHIMICA ACTA, 2005, 88 (07) : 1682 - 1701
  • [4] Chiral recognition in adrenergic receptor binding mimics prepared by molecular imprinting
    Ramstrom, O
    Yu, C
    Mosbach, K
    JOURNAL OF MOLECULAR RECOGNITION, 1996, 9 (5-6) : 691 - 696
  • [5] Three Hydrogen Bond Donor Catalysts: Oxyanion Hole Mimics and Transition State Analogues
    Beletskiy, Evgeny V.
    Schmidt, Jacob
    Wang, Xue-Bin
    Kass, Steven R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (45) : 18534 - 18537
  • [6] A cleft type receptor which combines an oxyanion hole with electrostatic interactions
    Rubio, Omayra H.
    del Mazo, Sara
    Monleon, Laura M.
    Simon, Luis
    Temprano, Alvaro G.
    Moran, Joaquin R.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (21) : 4571 - 4578
  • [7] Enantiomerically pure thrombin inhibitors for exploring the molecular recognition features of the oxyanion hole
    Schärer, K
    Morgenthaler, M
    Seiler, P
    Diederich, F
    Banner, DW
    Tschopp, T
    Obst-Sander, U
    HELVETICA CHIMICA ACTA, 2004, 87 (10) : 2517 - 2538
  • [8] Chromogenic receptor: From cation recognition to chiral recognition
    Kubo, Y
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (06) : 506 - 516
  • [9] A macrocyclic receptor for the chiral recognition of hydroxycarboxylates
    Tejeda, A
    Oliva, AI
    Simón, L
    Grande, M
    Caballero, MC
    Morán, JR
    TETRAHEDRON LETTERS, 2000, 41 (23) : 4563 - 4566
  • [10] CUTINASE, A LIPOLYTIC ENZYME WITH A PREFORMED OXYANION HOLE
    MARTINEZ, C
    NICOLAS, A
    VANTILBEURGH, H
    EGLOFF, MP
    CUDREY, C
    VERGER, R
    CAMBILLAU, C
    BIOCHEMISTRY, 1994, 33 (01) : 83 - 89