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Issue 20, 2012
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Sequence/structure relationships in aromatic dipeptide hydrogels formed under thermodynamic control by enzyme-assisted self-assembly†

Meghan Hughes,a   Pim W. J. M. Frederix,ab   Jaclyn Raeburn,c   Louise S. Birchall,a   Jan Sadownik,a   Fiona C. Coomer,a   I-Hsin Lin,d   Edmund J. Cussen,a   Neil T. Hunt,b   Tell Tuttle,a   Simon J. Webb,d   Dave J. Adamsc  and  Rein V. Ulijn*a  
Author affiliations

* Corresponding authors

a WestCHEM, Dept of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, UK
E-mail: rein.ulijn@strath.ac.uk

b SUPA, Department of Physics, University of Strathclyde, 107 Rottenrow East, Glasgow, UK

c Department of Chemistry, University of Liverpool, Crown Street, Liverpool, UK

d Department of Chemistry and Manchester Interdisciplinary Biocentre, University of Manchester, 131 Princess Street, Manchester, UK

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 β-sheets which interlock via π-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.

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

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Article information

https://doi.org/10.1039/C2SM25224D
Submitted
30 Jan 2012
Accepted
19 Mar 2012
First published
13 Apr 2012
Soft Matter, 2012,8, 5595-5602
Article type
Paper
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Sequence/structure relationships in aromatic dipeptide hydrogels formed under thermodynamic control by enzyme-assisted self-assembly

M. Hughes, P. W. J. M. Frederix, J. Raeburn, L. S. Birchall, J. Sadownik, F. C. Coomer, I. Lin, E. J. Cussen, N. T. Hunt, T. Tuttle, S. J. Webb, D. J. Adams and R. V. Ulijn, Soft Matter, 2012, 8, 5595
DOI: 10.1039/C2SM25224D

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