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Biomimetic macrocyclic receptors for carboxylate anion recognition based on C-linked peptidocalix[4]arenes

By Francesco Sansone, Laura Baldini, Alessandro Casnati, Marcio Lazzarotto, Franco Ugozzoli and Rocco Ungaro

Abstract

Two neutral macrobicyclic anion receptors 4 and 6, containing a calix[4]arene in the cone conformation, two l-alanine units, and a 2,6-diacylpyridine or a phthaloyl bridge, are described. The x-ray crystal structure of the acetone complexes of the pyridine containing macrocycle 6 shows the four amide NH groups to be in close proximity to the chiral pocket delimited by the pyridine and one aromatic nucleus of the calix[4]arene. This conformation is also the most stable in acetone-d6 solution, as proven by one- and two-dimensional NMR spectral measurements. Electrospray ionization–MS and 1H NMR experiments reveal that the two ligands strongly bind carboxylate anions in acetone solution. H-bonding interactions between the carboxylate anions and the amide NH groups, together with π/π stacking, are invoked to explain the efficiency and the selectivity of these anion receptors

Topics: Physical Sciences
Publisher: National Academy of Sciences
Year: 2002
DOI identifier: 10.1073/pnas.062625499
OAI identifier: oai:pubmedcentral.nih.gov:122680
Provided by: PubMed Central
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