title: Dynamic formation of hybrid peptidic capsules by chiral self-sorting and self-assembly.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, M. Kasprzaka 44/52, 01-224 Warsaw (Poland).
authors.forename: Hanna
authors.initials: H
authors.lastname: Jędrzejewska
authors.forename: Michał
authors.initials: M
authors.lastname: Wierzbicki
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.forename: Kari
authors.initials: K
authors.lastname: Rissanen
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Szumna
mesh_terms: D010455:Peptides / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D010455:Peptides
keywords: calixarenes; chirality; self-assembly; self-sorting; supramolecular chemistry