Journal of Medicinal Chemistry
Journal of Medicinal Chemistry
5 years ago

Halogen Bonding in Nucleic Acid Complexes

Halogen Bonding in Nucleic Acid Complexes
Oriana Tabarrini, Michal H. Kolář
Halogen bonding (X-bonding) has attracted notable attention among noncovalent interactions. This highly directional attraction between a halogen atom and an electron donor has been exploited in knowledge-based drug design. A great deal of information has been gathered about X-bonds in protein–ligand complexes, as opposed to nucleic acid complexes. Here we provide a thorough analysis of nucleic acid complexes containing either halogenated building blocks or halogenated ligands. We analyzed close contacts between halogens and electron-rich moieties. The phosphate backbone oxygen is clearly the most common halogen acceptor. We identified 21 X-bonds within known structures of nucleic acid complexes. A vast majority of the X-bonds is formed by halogenated nucleobases, such as bromouridine, and feature excellent geometries. Noncovalent ligands have been found to form only interactions with suboptimal interaction geometries. Hence, the first X-bonded nucleic acid binder remains to be discovered.

Publisher URL: http://dx.doi.org/10.1021/acs.jmedchem.7b00329

DOI: 10.1021/acs.jmedchem.7b00329

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