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Title: Co-assembly of Peptide Amphiphiles and Lipids into Supramolecular Nanostructures Driven by Anion–π Interactions

Abstract

Co-assembly of binary systems driven by specific non-covalent interactions can greatly expand the structural and functional space of supramolecular nanostructures. We report here on the self-assembly of peptide amphiphiles and fatty acids driven primarily by anion–π interactions. The peptide sequences investigated were functionalized with a perfluorinated phenylalanine residue to promote anion–π interactions with carboxylate headgroups in fatty acids. These interactions were verified here by NMR and circular dichroism experiments as well as investigated using atomistic simulations. Positioning the aromatic units close to the N-terminus of the peptide backbone near the hydrophobic core of cylindrical nanofibers leads to strong anion–π interactions between both components. With a low content of dodecanoic acid in this position, the cylindrical morphology is preserved. However, as the aromatic units are moved along the peptide backbone away from the hydrophobic core, the interactions with dodecanoic acid transform the cylindrical supramolecular morphology into ribbon-like structures. Increasing the ratio of dodecanoic acid to PA leads to either the formation of large vesicles in the binary systems where the anion–π interactions are strong, or a heterogeneous mixture of assemblies when the peptide amphiphiles associate weakly with dodecanoic acid. Furthermore, our findings reveal how co-assembly involving designed specific interactions can drasticallymore » change supramolecular morphology and even cross from nano to micro scales.« less

Authors:
 [1];  [1];  [1]; ORCiD logo [2];  [3];  [1]; ORCiD logo [3]; ORCiD logo [2]
+ Show Author Affiliations
  1. Northwestern Univ., Evanston, IL (United States)
  2. Northwestern Univ., Evanston, IL (United States); Northwestern Univ., Chicago, IL (United States)
  3. Nanyang Technological Univ. (Singapore)
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Energy Science (CBES); Northwestern Univ., Evanston, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1846932
Alternate Identifier(s):
OSTI ID: 1821221
Grant/Contract Number:  
FG02-08ER46539; FG02-00ER45810; AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 139; Journal Issue: 23; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 99 GENERAL AND MISCELLANEOUS; Supramolecular chemistry; Morphology; Peptides and proteins; Mathematical methods; Molecular interactions

Citation Formats

Yu, Zhilin, Erbas, Aykut, Tantakitti, Faifan, Palmer, Liam C., Jackman, Joshua A., Olvera de la Cruz, Monica, Cho, Nam-Joon, and Stupp, Samuel I. Co-assembly of Peptide Amphiphiles and Lipids into Supramolecular Nanostructures Driven by Anion–π Interactions. United States: N. p., 2017. Web. doi:10.1021/jacs.7b02058.
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Yu, Zhilin, Erbas, Aykut, Tantakitti, Faifan, Palmer, Liam C., Jackman, Joshua A., Olvera de la Cruz, Monica, Cho, Nam-Joon, & Stupp, Samuel I. Co-assembly of Peptide Amphiphiles and Lipids into Supramolecular Nanostructures Driven by Anion–π Interactions. United States. https://doi.org/10.1021/jacs.7b02058
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Yu, Zhilin, Erbas, Aykut, Tantakitti, Faifan, Palmer, Liam C., Jackman, Joshua A., Olvera de la Cruz, Monica, Cho, Nam-Joon, and Stupp, Samuel I. Thu . "Co-assembly of Peptide Amphiphiles and Lipids into Supramolecular Nanostructures Driven by Anion–π Interactions". United States. https://doi.org/10.1021/jacs.7b02058. https://www.osti.gov/servlets/purl/1846932.
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@article{osti_1846932,
title = {Co-assembly of Peptide Amphiphiles and Lipids into Supramolecular Nanostructures Driven by Anion–π Interactions},
author = {Yu, Zhilin and Erbas, Aykut and Tantakitti, Faifan and Palmer, Liam C. and Jackman, Joshua A. and Olvera de la Cruz, Monica and Cho, Nam-Joon and Stupp, Samuel I.},
abstractNote = {Co-assembly of binary systems driven by specific non-covalent interactions can greatly expand the structural and functional space of supramolecular nanostructures. We report here on the self-assembly of peptide amphiphiles and fatty acids driven primarily by anion–π interactions. The peptide sequences investigated were functionalized with a perfluorinated phenylalanine residue to promote anion–π interactions with carboxylate headgroups in fatty acids. These interactions were verified here by NMR and circular dichroism experiments as well as investigated using atomistic simulations. Positioning the aromatic units close to the N-terminus of the peptide backbone near the hydrophobic core of cylindrical nanofibers leads to strong anion–π interactions between both components. With a low content of dodecanoic acid in this position, the cylindrical morphology is preserved. However, as the aromatic units are moved along the peptide backbone away from the hydrophobic core, the interactions with dodecanoic acid transform the cylindrical supramolecular morphology into ribbon-like structures. Increasing the ratio of dodecanoic acid to PA leads to either the formation of large vesicles in the binary systems where the anion–π interactions are strong, or a heterogeneous mixture of assemblies when the peptide amphiphiles associate weakly with dodecanoic acid. Furthermore, our findings reveal how co-assembly involving designed specific interactions can drastically change supramolecular morphology and even cross from nano to micro scales.},
doi = {10.1021/jacs.7b02058},
journal = {Journal of the American Chemical Society},
number = 23,
volume = 139,
place = {United States},
year = {Thu Jun 01 00:00:00 EDT 2017},
month = {Thu Jun 01 00:00:00 EDT 2017}
}
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