Orthogonal Halogen-Bonding-Driven 3D Supramolecular Assembly of Right-Handed Synthetic Helical Peptides

Authors

Peng Teng, University of South Florida
Geoffrey M. Gray, University of South Florida
Mengmeng Zheng, University of South Florida
Sylvia Singh, University of South Florida
Xiaopeng Li, University of South FloridaFollow
Lukasz Wojtas, University of South FloridaFollow
Arjan van der Vaart, University of South Florida
Jianfeng Cai, University of South FloridaFollow

Document Type

Article

Publication Date

2019

Keywords

foldamers, halogen bonding, peptides, self-assembly, structure elucidation

Digital Object Identifier (DOI)

https://doi.org/10.1002/anie.201903259

Abstract

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.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Angewandte Chemie International Edition, v. 58, issue 23, p. 7778-7782

Scholar Commons Citation

Teng, Peng; Gray, Geoffrey M.; Zheng, Mengmeng; Singh, Sylvia; Li, Xiaopeng; Wojtas, Lukasz; van der Vaart, Arjan; and Cai, Jianfeng, "Orthogonal Halogen-Bonding-Driven 3D Supramolecular Assembly of Right-Handed Synthetic Helical Peptides" (2019). Chemistry Faculty Publications. 208.
https://digitalcommons.usf.edu/chm_facpub/208