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Controlled Construction of Cyclic d / l Peptide Nanorods
Author(s) -
Silk Mitchell R.,
Mohanty Biswaranjan,
Sampson Joanne B.,
Scanlon Martin J.,
Thompson Philip E.,
Chalmers David K.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811910
Subject(s) - nanorod , covalent bond , nanomaterials , peptide , nanostructure , cyclic peptide , chemistry , cycloaddition , intramolecular force , nanotechnology , combinatorial chemistry , materials science , stereochemistry , organic chemistry , biochemistry , catalysis
Cyclic d / l peptides (CPs) assemble spontaneously via backbone H‐bonding to form extended nanostructures. These modular materials have great potential as versatile bionanomaterials. However, the useful development of CP nanomaterials requires practical methods to direct and control their assembly. In this work, we present novel, heterogeneous, covalently linked CP tetramers that achieve local control over the CP subunit order and composition through coupling of amino acid side‐chains using copper‐activated azide–alkyne cycloaddition and disulfide bond formation. Cryo‐transmission electron microscopy revealed the formation of highly ordered, fibrous nanostructures, while NMR studies showed that these systems have strong intramolecular H‐bonding in solution. The introduction of inter‐CP tethers is expected to enable the development of complex nanomaterials with controllable chemical properties, facilitating the development of precisely functionalized or “decorated” peptide nanostructures.