Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

• Published in: International journal of molecular sciences Vol. 21; no. 19; p. 7206
• Main Authors: Nazarova, Anastasia, Shurpik, Dmitriy, Padnya, Pavel, Mukhametzyanov, Timur, Cragg, Peter, Stoikov, Ivan
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.10.2020; MDPI
• Subjects: (1S)-(+)-10-camphorsulfonic acid; Aggregates; aggregation; Alanine; amino acid; Amino acids; Amino Acids - chemistry; Ammonium; Ammonium compounds; Ammonium Compounds - chemistry; Ammonium paratungstate; Aromatic compounds; Azo Compounds - chemistry; Binding sites; Calixarenes - chemistry; Camphor - analogs & derivatives; Camphor - chemistry; Catalysts; Chemical properties; Circular dichroism; Composition; Cotton; Dichroism; Dyes; Glycine; host-guest systems; Identification and classification; L-Alanine; Magnetic Resonance Spectroscopy; Mass spectrometry; methyl orange dye; Models, Molecular; Nitrogen; NMR; NMR spectroscopy; Nuclear magnetic resonance; Peptides; pillararene; Quaternary Ammonium Compounds - chemistry; Reagents; Scientific imaging; Self-assembly; Stereoselectivity; Supramolecular compounds; Water - chemistry; Russia; methyl orange dye; aggregation; host-guest systems; (1S)-(+)-10-camphorsulfonic acid; amino acid; pillararene
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms21197206

Novel water-soluble multifunctional pillar[ ]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid ( -CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and H NMR spectroscopy. This work demonstrates the first case of using -CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[ ]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of -CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.