Interlaced capsules by self-assembly of cavitands substituted with tripeptides and tetrapeptides

Abstract

<p>A strategy that utilizes macrocyclic resorcin[4]arenes for the pre-positioning of peptides to form cavitands that subsequently self-assemble through hydrogen bonds was used for the formation of molecular capsules. Hydrophobic tri- and tetrapeptides were attached via their <i>C</i>-termini to tetraformylresorcin[4]arene using acylhydrazone linkers. The resulting cavitands self-assemble in relatively non-polar environments (chloroform or chloroform-methanol) forming non-covalent dimers through hydrogen bonding motifs resembling beta-sheets. NMR studies (ROESY and DOSY) indicate that the binding motif involves <i>C</i>-terminal amino acids from the peptide strands, while the <i>N</i>-terminal parts are positioned outside of the cavity. The capsules possess stable porous structures and they are able to quantitatively complex fullerenes C₆₀ and C₇₀.</p