Dynamic Formation of Hybrid Peptidic Capsules by Chiral Self‐Sorting and Self‐Assembly |
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Authors: | Hanna Jędrzejewska Michał Wierzbicki Dr. Piotr Cmoch Prof. Kari Rissanen Prof. Agnieszka Szumna |
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Affiliation: | 1. Institute of Organic Chemistry, Polish Academy of Sciences, M. Kasprzaka 44/52, 01‐224 Warsaw (Poland);2. Department of Chemistry, Nanoscience Center, University of Jyv?skyl?, P.O. Box 35, FI‐40014 (Finland) |
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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. |
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Keywords: | calixarenes chirality self‐assembly self‐sorting supramolecular chemistry |
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