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Towards the understanding of halogenation in peptide hydrogels : a quantum chemical approach

(2021) MATERIALS ADVANCES. 2(14). p.4792-4803
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Abstract
Non-covalent interactions involving aromatic rings play a central role in many areas of modern chemistry. In medicinal and bioorganic chemistry, the intermolecular interactions between the aromatic side chains of amino acids, such as phenylalanine and tyrosine, are of great interest. To enhance the affinity between such aromatic side chains, halogenation is a promising modification strategy. In the current work, the nature and strength of halogenated pi-pi stacked phenylalanine (Phe) dimers have been investigated using density functional theory, energy decomposition analyses and the non-covalent interaction (NCI) method. Our analysis shows that increasing the degree of halogenation enhances the strength of the stacking interactions and, moreover, the heavier halides (Cl, Br and I) lead to stronger interactions compared to the lighter F. This effect was traced back to local secondary interactions of the halide with the aliphatic C-H bonds of the phenylalanine side chain. Based on the computational findings, a set of peptide hydrogelators was synthesized, and the resulting hydrogel properties were further investigated via dynamic rheometry. Experimental observations can be correlated to the trends found in the theoretical analysis, suggesting that local interactions indeed play a noticeable role in enhancing peptide-based hydrogel strength.
Keywords
DENSITY-FUNCTIONAL THEORY, CORRELATED MOLECULAR CALCULATIONS, GAUSSIAN-BASIS SETS, NONCOVALENT INTERACTIONS, PI INTERACTIONS, AROMATIC INTERACTIONS, CONTROLLED-RELEASE, M06 SUITE, CATION-PI, STACKING

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MLA
Bettens, Tom, et al. “Towards the Understanding of Halogenation in Peptide Hydrogels : A Quantum Chemical Approach.” MATERIALS ADVANCES, vol. 2, no. 14, 2021, pp. 4792–803, doi:10.1039/d1ma00455g.
APA
Bettens, T., Lacanau, V., Van Lommel, R., De Maeseneer, T., Vandeplassche, W., Bertouille, J., … Alonso, M. (2021). Towards the understanding of halogenation in peptide hydrogels : a quantum chemical approach. MATERIALS ADVANCES, 2(14), 4792–4803. https://doi.org/10.1039/d1ma00455g
Chicago author-date
Bettens, Tom, Valentin Lacanau, Ruben Van Lommel, Tess De Maeseneer, Wouter Vandeplassche, Jolien Bertouille, Joost Brancart, et al. 2021. “Towards the Understanding of Halogenation in Peptide Hydrogels : A Quantum Chemical Approach.” MATERIALS ADVANCES 2 (14): 4792–4803. https://doi.org/10.1039/d1ma00455g.
Chicago author-date (all authors)
Bettens, Tom, Valentin Lacanau, Ruben Van Lommel, Tess De Maeseneer, Wouter Vandeplassche, Jolien Bertouille, Joost Brancart, Thomas M. A. Barlow, Tatiana Woller, Niko Van den Brande, Paula Moldenaers, Frank De Proft, Annemieke Madder, Richard Hoogenboom, Charlotte Martin, Steven Ballet, and Mercedes Alonso. 2021. “Towards the Understanding of Halogenation in Peptide Hydrogels : A Quantum Chemical Approach.” MATERIALS ADVANCES 2 (14): 4792–4803. doi:10.1039/d1ma00455g.
Vancouver
1.
Bettens T, Lacanau V, Van Lommel R, De Maeseneer T, Vandeplassche W, Bertouille J, et al. Towards the understanding of halogenation in peptide hydrogels : a quantum chemical approach. MATERIALS ADVANCES. 2021;2(14):4792–803.
IEEE
[1]
T. Bettens et al., “Towards the understanding of halogenation in peptide hydrogels : a quantum chemical approach,” MATERIALS ADVANCES, vol. 2, no. 14, pp. 4792–4803, 2021.
@article{8724360,
  abstract     = {{Non-covalent interactions involving aromatic rings play a central role in many areas of modern chemistry. In medicinal and bioorganic chemistry, the intermolecular interactions between the aromatic side chains of amino acids, such as phenylalanine and tyrosine, are of great interest. To enhance the affinity between such aromatic side chains, halogenation is a promising modification strategy. In the current work, the nature and strength of halogenated pi-pi stacked phenylalanine (Phe) dimers have been investigated using density functional theory, energy decomposition analyses and the non-covalent interaction (NCI) method. Our analysis shows that increasing the degree of halogenation enhances the strength of the stacking interactions and, moreover, the heavier halides (Cl, Br and I) lead to stronger interactions compared to the lighter F. This effect was traced back to local secondary interactions of the halide with the aliphatic C-H bonds of the phenylalanine side chain. Based on the computational findings, a set of peptide hydrogelators was synthesized, and the resulting hydrogel properties were further investigated via dynamic rheometry. Experimental observations can be correlated to the trends found in the theoretical analysis, suggesting that local interactions indeed play a noticeable role in enhancing peptide-based hydrogel strength.}},
  author       = {{Bettens, Tom and Lacanau, Valentin and Van Lommel, Ruben and De Maeseneer, Tess and Vandeplassche, Wouter and Bertouille, Jolien and Brancart, Joost and Barlow, Thomas M. A. and Woller, Tatiana and Van den Brande, Niko and Moldenaers, Paula and De Proft, Frank and Madder, Annemieke and Hoogenboom, Richard and Martin, Charlotte and Ballet, Steven and Alonso, Mercedes}},
  issn         = {{2633-5409}},
  journal      = {{MATERIALS ADVANCES}},
  keywords     = {{DENSITY-FUNCTIONAL THEORY,CORRELATED MOLECULAR CALCULATIONS,GAUSSIAN-BASIS SETS,NONCOVALENT INTERACTIONS,PI INTERACTIONS,AROMATIC INTERACTIONS,CONTROLLED-RELEASE,M06 SUITE,CATION-PI,STACKING}},
  language     = {{eng}},
  number       = {{14}},
  pages        = {{4792--4803}},
  title        = {{Towards the understanding of halogenation in peptide hydrogels : a quantum chemical approach}},
  url          = {{http://doi.org/10.1039/d1ma00455g}},
  volume       = {{2}},
  year         = {{2021}},
}

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