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

ABSTRACT: 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.

SUBMITTER: Sanders AM

PROVIDER: S-EPMC6640940 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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

Sanders Allix M AM Kale Tejaswini S TS Katz Howard E HE Tovar John D JD

ACS omega 20170207 2

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 t ...[more]

PMID: 31457447

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