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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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Funding

The work was financially supported by the Russian Science Foundation (project no. 18-73-10094).

The registration of mass spectra was funded from the budget of the Priority-2030 Strategic Academic Leadership Program, Kazan (Volga Region) Federal University.

The study of aggregation properties was funded from the grant of the President of the Russian Federation for state support of the young Russian PhD scientists (grant no. MK-723.2021.1.3).

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Authors and Affiliations

  1. Kazan (Volga region) Federal University, Butlerov Chemistry Institute, 420008, Kazan, Russia

    A. A. Nazarova, V. R. Sultanaev, L. S. Yakimova & I. I. Stoikov

Authors
  1. A. A. Nazarova
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  2. V. R. Sultanaev
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  3. L. S. Yakimova
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  4. I. I. Stoikov
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Corresponding authors

Correspondence to A. A. Nazarova, L. S. Yakimova or I. I. Stoikov.

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The authors declare no conflict of interest.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 8, pp. 832–840 https://doi.org/10.31857/S0514749222080079.

In memory of Academician A.I. Konovalov

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Nazarova, A.A., Sultanaev, V.R., Yakimova, L.S. et al. Synthesis and Supramolecular Properties of Water-soluble Pillar[5]arenes Containig Amino Acid Residues. Russ J Org Chem 58, 1115–1122 (2022). https://doi.org/10.1134/S1070428022080073

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