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

Pillar[5]arene/albumin biosupramolecular systems for simultaneous native protein preservation and encapsulation of a water-soluble substrate

“…It is obvious that the observed effects are associated with the structural and spatial features of the synthesized betaine macrocycles. Based on the works previously published by our scientific group, 31,32,39 we can conclude that macrocycle 4 predominantly forms compact α-helix type secondary structures with a pre-organized structure. It promotes the formation of compact host–guest complexes.…”

“…In our previous works, we synthesized ester derivatives of pillar [5]arene with amino acid fragments of L-phenylalanine, 31 L-alanine, and glycine. 32 These synthesized macrocycles exhibited self-assembly features and the ability to form nanosized particles in the absence or presence of substrates. In order to further develop the research on pillar [5]arene derivatives, we hydrolyzed ester macrocycles 1-3 to obtain water-soluble carboxybetaine structures 4-6 containing fragments of essential amino acids (Scheme 1).…”

Decasubstituted Pillar[5]arene Derivatives Containing L-Tryptophan and L-Phenylalanine Residues: Non-Covalent Binding and Release of Fluorescein from Nanoparticles

“…Chiral amino acids are often used to functionalize macrocyclic platforms to create biomimetic receptors. Up to date, the literature presents a number of works dedicated to the introduction of amino acid fragments, both aromatic and aliphatic, into the structure of pillar [5]arenes [8,9]. The introduction of aromatic amino acid substituents into the structure of pillar [5]arenes make it possible to fix a certain conformation, increase solubility in water, and the number of additional interaction centers to improve the receptor properties of macrocycles.…”