biostudies-literatureUnknown10Sakowicz AMWe present the synthesis of new chiral water-soluble dimeric capsules by the multicomponent Mannich reaction between charged amino acids (glutamic acid or arginine), resorcinarene, and formaldehyde and by subsequent self-assembly. The zwitterionic character of the backbones enables electrostatic interactions between arms and induces self-assembly of dimeric capsules, namely, (L-ArgR)2 and (L-GluR)2, in water with a wide range of pH, as demonstrated by NMR, diffusion coefficient measurement, and circular dichroism. The assembly/disassembly processes are fast on the NMR timescale. This mode of dimerization leaves side chains available for additional interactions and creates chiral cavities of mixed hydrophobic/hydrophilic character. According to this charaFrontiers in chemistry883093https://www.ebi.ac.uk/biostudies/studies/S-EPMC9047736biostudies-literatureChiral Water-Soluble Molecular Capsules With Amphiphilic Interiors.PMC9047736Sakowicz AMSzumna AfalseChiral Water-Soluble Molecular Capsules With Amphiphilic Interiors.We present the synthesis of new chiral water-soluble dimeric capsules by the multicomponent Mannich reaction between charged amino acids (glutamic acid or arginine), resorcinarene, and formaldehyde and by subsequent self-assembly. The zwitterionic character of the backbones enables electrostatic interactions between arms and induces self-assembly of dimeric capsules, namely, (L-ArgR)2 and (L-GluR)2, in water with a wide range of pH, as demonstrated by NMR, diffusion coefficient measurement, and circular dichroism. The assembly/disassembly processes are fast on the NMR timescale. This mode of dimerization leaves side chains available for additional interactions and creates chiral cavities of mixed hydrophobic/hydrophilic character. According to this chara2022-01-01T00:00:00Z20222025-04-25T22:58:28.135Z2025-04-06T09:12:52.667ZS-EPMC90477363549463210.3389/fchem.2022.883093