Structural self-sorting of pseudopeptide homo and heterodimeric disulfide cages in water: mechanistic insights and cation sensing

Abstract

Water-soluble, multi-component disulfide cages showing a self-sorting behavior and cation sensing ability.

Recent trends in organic cage synthesis: push towards water-soluble organic cages

“…One such example is the disulfide (–S–S–) bond formation reaction, which was used by Otto et al to generate different macrocycles in water. 46 The same disulfide chemistry has also been explored by Stefankiewicz et al in the synthesis of cages. They also demonstrated the dynamic nature of the disulfide bond in water through the formation of homo and heterodimeric cages.…”

“…However, the loss of geometrical compatibility with large size differences resulted in self-sorting of the dynamic library into a pair of two homodimeric cages. 46…”

Specific Noncovalent Association of Truncated exo-Functionalized Triangular Homochiral Isotrianglimines through Head-to-Head, Tail-to-Tail, and Honeycomb Supramolecular Motifs

“… 7 − 10 This approach allows for the construction of capsules with large internal cavities and is capable of capturing neutral and charged species in addition polymeric structures, where the monomers are bound by noncovalent interactions. 11 − 15 …”

Expanding structural diversity in a library of disulfide macrocycles through in-situ imide hydrolysis

“…Recently, there has been a growing interest in the search for new methods and conditions for the oxidation of thiols to disulfides in DCC using metalloid catalysis 13 , 14 , solvent effects 15 , iodine 16 or mechanochemical stimuli 17 – 19 . To date, numerous water-soluble disulfide systems of distinct topologies such as macrocycles, cages, catenanes or knots have been described, most of which are based on organic cysteine-functionalized components 20 – 29 . Macrocyclic structures, especially those based on modified naphthalenediimides (NDIs) have been heavily explored in the last decade as they present interesting properties and functions such as molecular sensors, host−guest complexes, molecular devices, catalysis through π-anion interactions and non-covalent binding with DNA for bio-applications 30 , 31 .…”