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Issue 4, 2015
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Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

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Abstract

We report the synthesis of a series of anionic dendritic peptide amphiphiles of increasing hydrophobic character. By establishing state diagrams we describe their pH and ionic strength triggered self-assembly into supramolecular nanorods in water and highlight the impact of hydrophobic shielding in the supramolecular polymerisation process. Via the incorporation of fluorinated peptide side chains the pH-triggered monomer to polymer transition at physiological ionic strength is shifted from pH 5.0 to pH 7.4. We thereby show that compensating attractive non-covalent interactions and hydrophobic effects with repulsive electrostatic forces, a concept we refer to as frustrated growth, is a sensitive tool in order to manipulate one-dimensional supramolecular polymerisation processes in water.

Graphical abstract: Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

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Publication details

The article was received on 15 Oct 2014, accepted on 12 Nov 2014 and first published on 13 Nov 2014


Article type: Paper
DOI: 10.1039/C4OB02185A
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Citation: Org. Biomol. Chem., 2015,13, 1030-1039
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    Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

    R. Appel, S. Tacke, J. Klingauf and P. Besenius, Org. Biomol. Chem., 2015, 13, 1030
    DOI: 10.1039/C4OB02185A

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