6533b7dafe1ef96bd126e2b0
RESEARCH PRODUCT
Dynamic formation of hybrid peptidic capsules by chiral self-sorting and self-assembly.
Kari RissanenMichał WierzbickiPiotr CmochAgnieszka SzumnaHanna Jędrzejewskasubject
ChemistryStereochemistryProton Magnetic Resonance SpectroscopySupramolecular chemistryDynamic covalent chemistryRegioselectivityStereoisomerismGeneral ChemistryGeneral MedicineResorcinareneInherent chiralityTautomerCatalysisSelf-assemblyChirality (chemistry)Peptidesta116description
Owing to their versatility and biocompatibility, peptide-based self-assembled structures constitute valuable targets for complex functional designs. It is now shown that artificial capsules based on β-barrel binding motifs can be obtained by means of dynamic covalent chemistry (DCC) and self-assembly. Short peptides (up to tetrapeptides) are reversibly attached to resorcinarene scaffolds. Peptidic capsules are thus selectively formed in either a heterochiral or a homochiral way by simultaneous and spontaneous processes, involving chiral sorting, tautomerization, diastereoselective induction of inherent chirality, and chiral self-assembly. Self-assembly is shown to direct the regioselectivity of reversible chemical reactions. It is also responsible for shifting the tautomeric equilibrium for one of the homochiral capsules. Two different tautomers (keto-enamine hemisphere and enol-imine hemisphere) are observed in this capsule, allowing the structure to adapt for self-assembly.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-10-08 | Angewandte Chemie (International ed. in English) |