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Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides
[Image: see text] 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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2017
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640940/ https://www.ncbi.nlm.nih.gov/pubmed/31457447 http://dx.doi.org/10.1021/acsomega.6b00414 |
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author | Sanders, Allix M. Kale, Tejaswini S. Katz, Howard E. Tovar, John D. |
author_facet | Sanders, Allix M. Kale, Tejaswini S. Katz, Howard E. Tovar, John D. |
author_sort | Sanders, Allix M. |
collection | PubMed |
description | [Image: see text] 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. |
format | Online Article Text |
id | pubmed-6640940 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66409402019-08-27 Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides Sanders, Allix M. Kale, Tejaswini S. Katz, Howard E. Tovar, John D. ACS Omega [Image: see text] 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. American Chemical Society 2017-02-07 /pmc/articles/PMC6640940/ /pubmed/31457447 http://dx.doi.org/10.1021/acsomega.6b00414 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Sanders, Allix M. Kale, Tejaswini S. Katz, Howard E. Tovar, John D. Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides |
title | Solid-Phase Synthesis of
Self-Assembling Multivalent π-Conjugated
Peptides |
title_full | Solid-Phase Synthesis of
Self-Assembling Multivalent π-Conjugated
Peptides |
title_fullStr | Solid-Phase Synthesis of
Self-Assembling Multivalent π-Conjugated
Peptides |
title_full_unstemmed | Solid-Phase Synthesis of
Self-Assembling Multivalent π-Conjugated
Peptides |
title_short | Solid-Phase Synthesis of
Self-Assembling Multivalent π-Conjugated
Peptides |
title_sort | solid-phase synthesis of
self-assembling multivalent π-conjugated
peptides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640940/ https://www.ncbi.nlm.nih.gov/pubmed/31457447 http://dx.doi.org/10.1021/acsomega.6b00414 |
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