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Self-assembly of tripeptides into γ-turn nanostructures

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Abstract

Self-assembling phenylalanine-based peptides have garnered interest owing to their potential for creating new functional materials. Here, we designed four diastereomers, L-Phe-L-Phe-L-Phe (FFF), D-Phe-L-Phe-L-Phe (fFF), L-Phe-D-Phe-L-Phe (FfF) and L-Phe-L-Phe-D-Phe (FFf), to analyze the effect of the D-isomer on the self-assembly. Using SEM, TG, VCD, and solid-state NMR measurements, we found that only FFf forms a γ-turn conformation and self-assembles into a nanoplate with higher thermal stability. The supramolecular structure of FFf consists of intra- and intermolecular hydrogen bonds and π–π stackings. From our results, we have discovered that FFf forms a new type of self-assembling γ-turn conformation, clarifying the structural role of a D-amino acid residue in supramolecular formation.

Graphical abstract: Self-assembly of tripeptides into γ-turn nanostructures

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Publication details

The article was received on 14 Jan 2019, accepted on 27 Mar 2019 and first published on 27 Mar 2019


Article type: Communication
DOI: 10.1039/C9CP00233B
Citation: Phys. Chem. Chem. Phys., 2019, Advance Article

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    Self-assembly of tripeptides into γ-turn nanostructures

    Y. Ozawa, H. Sato, Y. Kayano, N. Yamaki, Y. Izato, A. Miyake, A. Naito and I. Kawamura, Phys. Chem. Chem. Phys., 2019, Advance Article , DOI: 10.1039/C9CP00233B

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