Evaluation of the binding ability of tetraaza[2]arene[2]triazine receptors anchoring L-alanine units for aromatic carboxylate anions
authors Vicente, AI; Caio, JM; Sardinha, J; Moiteiro, C; Delgado, R; Felix, V
nationality International
journal TETRAHEDRON
author keywords Macrocycles; Azacalixarenes; Anion recognition; Carboxylate anions; Molecular dynamics
keywords DIMETHYL-SULFOXIDE; MOLECULAR RECOGNITION; CAVITY; COMPLEXATION; ACIDS; DEPROTONATION; EQUILIBRIA; CHEMISTRY; TRIAZINE; FLUORIDE
abstract The binding affinities of three new tetraaza[2]arene[2]triazine based macrocycles anchoring one (AC1A) and two (AC2A and Me(4)AC2A) t-alanine amino acid units for five aromatic carboxylate anions (bz(-), ph(2-), iph(2-), tph(2-) and btc(3-)) were investigated in DMSO-d(6). H-1 NMR titrations revealed that the AC1A and AC2A receptors exhibit comparable anion affinities, suggesting that the two t-alanine binding units in AC2A are not simultaneously involved in the anion recognition as indicated by molecular dynamics simulations carried out for selected AC1A and AC2A associations using the AMBER force field (GAFF). New force field parameters were developed in order to mimic the structural singularity derived from the N-H macrocyclic bridges. (C) 2011 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4020
year published 2012
volume 68
issue 2
beginning page 670
ending page 680
digital object identifier (doi) 10.1016/j.tet.2011.10.090
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000299443900035
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