Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides
Abstract
Here, we present a completely solid-phase synthetic strategy to create three- and four-fold peptide-appended π-electron molecules, where the multivalent oligopeptide presentation is dictated by the symmetries of reactive handles placed on discotic π-conjugated cores. Carboxylic acid and anhydride groups were viable amidation and imidation partners, respectively, and oligomeric π-electron discotic cores were prepared through Pd-catalyzed cross-couplings. Due to intermolecular hydrogen bonding between the three or four peptide axes, these π-peptide hybrids self-assemble into robust one-dimensional nanostructures with high aspect ratios in aqueous solution. The preparation of these systems via solid-phase methods will be detailed along with their self-assembly properties, as revealed by steady-state spectroscopy and transmission electron microscopy and electrical characterization using field-effect transistor measurements.
- Authors:
-
[1];
[1]
- Department of Chemistry, Krieger School of Arts and Sciences, ‡Department of Materials Science and Engineering, Whiting School of Engineering, §Institute of NanoBioTechnology, Johns Hopkins University, 3400 N. Charles Street, Baltimore, Maryland 21218, United States
- Publication Date:
- Research Org.:
- John Hopkins Univ., Baltimore, MD (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1342800
- Alternate Identifier(s):
- OSTI ID: 1345216
- Grant/Contract Number:
- SC0004857
- Resource Type:
- Published Article
- Journal Name:
- ACS Omega
- Additional Journal Information:
- Journal Name: ACS Omega Journal Volume: 2 Journal Issue: 2; Journal ID: ISSN 2470-1343
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; bioelectronics; catalysts; electron microscopy; molecular structure; nanostructured materials; nanostructures; peptides and proteins; self-assembly
Citation Formats
Sanders, Allix M., Kale, Tejaswini S., Katz, Howard E., and Tovar, John D. Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides. United States: N. p., 2017.
Web. doi:10.1021/acsomega.6b00414.
Sanders, Allix M., Kale, Tejaswini S., Katz, Howard E., & Tovar, John D. Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides. United States. https://doi.org/10.1021/acsomega.6b00414
Sanders, Allix M., Kale, Tejaswini S., Katz, Howard E., and Tovar, John D. Tue .
"Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides". United States. https://doi.org/10.1021/acsomega.6b00414.
@article{osti_1342800,
title = {Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides},
author = {Sanders, Allix M. and Kale, Tejaswini S. and Katz, Howard E. and Tovar, John D.},
abstractNote = {Here, we present a completely solid-phase synthetic strategy to create three- and four-fold peptide-appended π-electron molecules, where the multivalent oligopeptide presentation is dictated by the symmetries of reactive handles placed on discotic π-conjugated cores. Carboxylic acid and anhydride groups were viable amidation and imidation partners, respectively, and oligomeric π-electron discotic cores were prepared through Pd-catalyzed cross-couplings. Due to intermolecular hydrogen bonding between the three or four peptide axes, these π-peptide hybrids self-assemble into robust one-dimensional nanostructures with high aspect ratios in aqueous solution. The preparation of these systems via solid-phase methods will be detailed along with their self-assembly properties, as revealed by steady-state spectroscopy and transmission electron microscopy and electrical characterization using field-effect transistor measurements.},
doi = {10.1021/acsomega.6b00414},
journal = {ACS Omega},
number = 2,
volume = 2,
place = {United States},
year = {Tue Feb 07 00:00:00 EST 2017},
month = {Tue Feb 07 00:00:00 EST 2017}
}
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https://doi.org/10.1021/acsomega.6b00414
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