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Privileged hydration sites in aromatic side chains: effect on conformational equilibrium

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Abstract

Water interaction with peptide chains is one of the key structure stabilizing factors in an aqueous environment. Because of its strong polar character, water can bind to both anionic and cationic sites via electrostatic interactions. It can also act as a hydrogen-bond donor or acceptor according to its interactions with different polar groups in the backbone and side chains of peptides and proteins. Based on density functional theory calculations, the present report aims at illustrating the most energetically favorable interaction sites of aromatic side chains of phenylalanine, tyrosine, tryptophan, and histidine (neutral and protonated species) with surrounding water molecules. It was shown that beyond the strong interactions occurring between water and the aromatic ring acceptor/donor sites, such as O–H, N–H and –N[double bond, length as m-dash] groups, weaker interactions with π-electron clouds should also be considered. The latter type of binding, hereafter referred to as Hw⋯π interaction, involves one of the water hydrogen atoms (Hw) pointing toward the aromatic ring. Upon comparison between the theoretical data obtained from a purely implicit hydration model, i.e. a polarized solvent continuum, and those collected from a mixture of implicit and explicit hydration models, it has been shown that the explicit water molecule binding to aromatic rings affects the relative energies of the rotamers generated by the two side chain torsion angles (χ1 and χ2).

Graphical abstract: Privileged hydration sites in aromatic side chains: effect on conformational equilibrium

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Publication details

The article was received on 12 Jul 2017, accepted on 28 Sep 2017 and first published on 29 Sep 2017


Article type: Paper
DOI: 10.1039/C7CP04685E
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
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    Privileged hydration sites in aromatic side chains: effect on conformational equilibrium

    B. Hernández, F. Pflüger, M. Dauchez and M. Ghomi, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP04685E

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