Chiral Water-Soluble Molecular Capsules With Amphiphilic Interiors.

ABSTRACT: 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 chara

SUBMITTER: Sakowicz AM 

PROVIDER: S-EPMC9047736 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature