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Issue 1, 2011
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Computational and experimental investigations of mono-septanoside binding by Concanavalin A: correlation of ligand stereochemistry to enthalpies of binding

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Abstract

Structure-energy relationships for a small group of pyranose and septanose mono-saccharide ligands are developed for binding to Concanavalin A (ConA). The affinity of ConA for methyl “manno” β-septanoside 7 was found to be higher than any of the previously reported mono-septanoside ligands. Isothermal titration calorimetry (ITC) in conjunction with docking simulations and quantum mechanics/molecular mechanics (QM/MM) modeling established the specific role of binding enthalpy in the structure–energy relations of ConA bound to natural mono-saccharides and unnatural mono-septanosides. An important aspect in the differential binding among ligands is the deformation energy required to reorganize internal hydroxyl groups upon binding of the ligand to ConA.

Graphical abstract: Computational and experimental investigations of mono-septanoside binding by Concanavalin A: correlation of ligand stereochemistry to enthalpies of binding

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Publication details

The article was received on 15 Jul 2010, accepted on 07 Oct 2010 and first published on 18 Nov 2010


Article type: Paper
DOI: 10.1039/C0OB00425A
Citation: Org. Biomol. Chem., 2011,9, 154-164
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    Computational and experimental investigations of mono-septanoside binding by Concanavalin A: correlation of ligand stereochemistry to enthalpies of binding

    M. R. Duff Jr., W. S. Fyvie, S. D. Markad, A. E. Frankel, C. V. Kumar, J. A. Gascón and M. W. Peczuh, Org. Biomol. Chem., 2011, 9, 154
    DOI: 10.1039/C0OB00425A

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