Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides

Sanders, Allix M.; Kale, Tejaswini S.; Katz, Howard E.; Tovar, John D.

doi:10.1021/acsomega.6b00414

Title: Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides

Journal Article · Tue Feb 07 00:00:00 EST 2017 · ACS Omega

DOI:https://doi.org/10.1021/acsomega.6b00414· OSTI ID:1342800

Sanders, Allix M. ^[1]; Kale, Tejaswini S. ^[1];

^[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

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.

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Research Organization:: John Hopkins Univ., Baltimore, MD (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0004857

OSTI ID:: 1342800

Alternate ID(s):: OSTI ID: 1345216

Journal Information:: ACS Omega, Journal Name: ACS Omega Vol. 2 Journal Issue: 2; ISSN 2470-1343

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 14 works

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Title: Solid-Phase Synthesis of Self-Assembling Multivalent π-Conjugated Peptides

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