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Orthogonal Halogen‐Bonding‐Driven 3D Supramolecular Assembly of Right‐Handed Synthetic Helical Peptides
Author(s) -
Teng Peng,
Gray Geoffrey M.,
Zheng Mengmeng,
Singh Sylvia,
Li Xiaopeng,
Wojtas Lukasz,
van der Vaart Arjan,
Cai Jianfeng
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903259
Subject(s) - supramolecular chemistry , hydrogen bond , intermolecular force , halogen bond , supramolecular assembly , self assembly , chemistry , peptide , halogen , rational design , molecular recognition , crystallography , combinatorial chemistry , molecule , stereochemistry , materials science , nanotechnology , crystal structure , organic chemistry , biochemistry , alkyl
Peptide‐mediated self‐assembly is a prevalent method for creating highly ordered supramolecular architectures. Herein, we report the first example of orthogonal C−X⋅⋅⋅X−C/C−X⋅⋅⋅π halogen bonding and hydrogen bonding driven crystalline architectures based on synthetic helical peptides bearing hybrids of l ‐sulfono‐γ‐AApeptides and natural amino acids. The combination of halogen bonding, intra‐/intermolecular hydrogen bonding, and intermolecular hydrophobic interactions enabled novel 3D supramolecular assembly. The orthogonal halogen bonding in the supramolecular architecture exerts a novel mechanism for the self‐assembly of synthetic peptide foldamers and gives new insights into molecular recognition, supramolecular design, and rational design of biomimetic structures.