Sequence/structure relationships in aromatic dipeptide hydrogels formed under thermodynamic control by enzyme-assisted self-assembly

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Hughes, Meghan and Frederix, Pim W. J. M. and Raeburn, Jaclyn and Birchall, Louise S. and Sadownik, Jan and Coomer, Fiona C. and Lin, I-Hsin and Cussen, Edmund J. and Hunt, Neil T. and Tuttle, Tell and Webb, Simon J. and Adams, Dave J. and Ulijn, Rein V. (2012) Sequence/structure relationships in aromatic dipeptide hydrogels formed under thermodynamic control by enzyme-assisted self-assembly. Soft Matter, 8 (20). pp. 5595-5602. ISSN 1744-6848 (https://doi.org/10.1039/c2sm25224d)

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Abstract

Self-assembled supramolecular structures of peptide derivatives often reflect a kinetically trapped state rather than the thermodynamically most favoured structure, which presents a challenge when trying to elucidate the molecular design rules for these systems. In this article we use thermodynamically controlled self-assembly, driven by enzymatic condensation of amino acid derivatives, to elucidate chemical composition/nanostructure relationships for four closely related Fmoc-dipeptide-methyl esters which form hydrogels; SF, SL, TF and TL. We demonstrate that each of the four systems self-assemble to form extended arrays of beta-sheets which interlock via pi-stacking of Fmoc-moieties, yet with subtle differences in molecular organisation as supported by rheology, fluorescence emission spectroscopy, infrared spectroscopy, X-ray diffraction analysis and molecular mechanics minimisation.

ORCID iDs

Hughes, Meghan, Frederix, Pim W. J. M., Raeburn, Jaclyn, Birchall, Louise S., Sadownik, Jan, Coomer, Fiona C., Lin, I-Hsin, Cussen, Edmund J. ORCID logoORCID: https://orcid.org/0000-0002-2899-6888, Hunt, Neil T. ORCID logoORCID: https://orcid.org/0000-0001-7400-5152, Tuttle, Tell, Webb, Simon J., Adams, Dave J. and Ulijn, Rein V. ORCID logoORCID: https://orcid.org/0000-0001-7974-3779;
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