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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...

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Autores principales: Sanders, Allix M., Kale, Tejaswini S., Katz, Howard E., Tovar, John D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
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.
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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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