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Issue 3, 2016
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STD NMR and molecular modelling insights into interaction of novel mannose-based ligands with DC-SIGN

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Abstract

Study of interaction of mannose-based ligands with receptor DC-SIGN using high resolution NMR in combination with molecular modelling showed that four α-D-mannoside ligands interact with the binding site predominantly through the mannose moiety. The other two aromatic groups that are bound to α-D-mannose through a glycerol linker demonstrate interaction that can be related to their substitution pattern. Ligand with naphthyl and meta-substituted phenyl ring exhibited the most favourable binding characteristics. In addition to the predicted hydrophobic interactions of aromatic moieties our results propose new contacts of substituted phenyl moiety in the more polar area of the flat binding site of DC-SIGN and thus offer new possibilities in further designing of novel, more potent DC-SIGN antagonists.

Graphical abstract: STD NMR and molecular modelling insights into interaction of novel mannose-based ligands with DC-SIGN

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Publication details

The article was received on 15 Sep 2015, accepted on 27 Oct 2015 and first published on 27 Oct 2015


Article type: Paper
DOI: 10.1039/C5OB01916H
Citation: Org. Biomol. Chem., 2016,14, 862-875
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    STD NMR and molecular modelling insights into interaction of novel mannose-based ligands with DC-SIGN

    A. Kotar, T. Tomašič, M. Lenarčič Živković, G. Jug, J. Plavec and M. Anderluh, Org. Biomol. Chem., 2016, 14, 862
    DOI: 10.1039/C5OB01916H

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