Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 50, Pages 13760-13764Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407802
Keywords
calixarenes; chirality; self-assembly; self-sorting; supramolecular chemistry
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Funding
- Foundation for Polish Science [POMOST/2011-4/10]
- National Science Center [2013/09/B/ST5/01026]
- Wroclaw Centre for Networking and Supercomputing [20299]
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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 -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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