Synthesis and Supramolecular Properties of Water-soluble Pillar[5]arenes Containig Amino Acid Residues

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Abstract
Novel water-soluble pillar[5]arenes containing both quaternary ammonium fragments and amino acid residues (Gly, l-Ala) were synthesized in good yields. Two-dimensional 1H–1H NOESY NMR spectroscopy and IR spectroscopy showed that the synthesized pillar[5]arenes tend to form different types of β-structures. The macrocycle containing glycine residues is characterized by the formation of β-sheets, while the pillar[5]arene containing L-alanine residues forms β-loops. Dynamic light scattering and transmission electron microscopy showed that the pillar[5]arene containing glycine fragments formed nanosized associates with an average hydrodynamic diameter of 150 nm, which was explained by a more compact packing of the substituents in this macrocycle.

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