Issue 31, 2021

Biological halogen bonds in protein–ligand complexes: a combined QTAIM and NCIPlot study in four representative cases

Abstract

In this study, the PDB has been manually scrutinized by using a subset of all PDB entries containing organic iodinated ligands. Four structures exhibiting short I⋯A halogen bonding (HaB) contacts (A stands for the σ-hole acceptor) have been selected and further analysed. In most hits, the sigma-hole acceptor corresponds to an O-atom of the amido group belonging to the protein backbone. In a minority of hits, the electron donors are O, S, Se or π-systems of the amino-acid side chains. A judicious selection of four PDB structures presenting all four types of HaB interactions (C–I⋯A, A = O, S, Se, π) has been performed. For these selected structures, a comprehensive RI-MP2/def2-TZVP study has been carried out to evaluate the HaB energetically. Moreover, the interactions have been characterized by combining the quantum theory of “atoms-in-molecules” (QTAIM) and the noncovalent interaction plot (NCIPlot) and rationalized using the molecular electrostatic potential (MEP) surface.

Graphical abstract: Biological halogen bonds in protein–ligand complexes: a combined QTAIM and NCIPlot study in four representative cases

Supplementary files

Article information

Article type
Paper
Submitted
23 jun. 2021
Accepted
19 jul. 2021
First published
19 jul. 2021

Org. Biomol. Chem., 2021,19, 6858-6864

Biological halogen bonds in protein–ligand complexes: a combined QTAIM and NCIPlot study in four representative cases

A. Frontera and A. Bauzá, Org. Biomol. Chem., 2021, 19, 6858 DOI: 10.1039/D1OB01212F

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