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 H-1 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 pi/pi stacking, are invoked to explain the efficiency and the selectivity of these anion receptors.

Biomimetic macrocyclic receptors for carboxylate anion recognition based on C-linked peptidocalix[4]arenes / F. SANSONE; L. BALDINI; A. CASNATI; M. LAZZAROTTO; F. UGOZZOLI; R. UNGARO. - In: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA. - ISSN 0027-8424. - 99:(2002), pp. 4842-4847. [10.1073/pnas.062625499]

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

SANSONE, Francesco;BALDINI, Laura;CASNATI, Alessandro;UGOZZOLI, Franco;UNGARO, Rocco
2002

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 H-1 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 pi/pi stacking, are invoked to explain the efficiency and the selectivity of these anion receptors.
Biomimetic macrocyclic receptors for carboxylate anion recognition based on C-linked peptidocalix[4]arenes / F. SANSONE; L. BALDINI; A. CASNATI; M. LAZZAROTTO; F. UGOZZOLI; R. UNGARO. - In: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA. - ISSN 0027-8424. - 99:(2002), pp. 4842-4847. [10.1073/pnas.062625499]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/1451883
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