3 years ago

Sulfur as an Acceptor to Bromine in Biomolecular Halogen Bonds

Sulfur as an Acceptor to Bromine in Biomolecular Halogen Bonds
Matthew Saxton, Melissa Coates Ford, P. Shing Ho
The halogen bond (X-bond) has become an important design element in chemistry, including medicinal chemistry and biomolecular engineering. Although oxygen is the most prevalent and best characterized X-bond acceptor in biomolecules, the interaction is seen with nitrogen, sulfur, and aromatic systems as well. In this study, we characterize the structure and thermodynamics of a Br···S X-bond between a 5-bromouracil base and a phosphorothioate in a model DNA junction. The single-crystal structure of the junction shows the geometry of the Br···S to be variable, while calorimetric studies show that the anionic S acceptor is comparable to or slightly more stable than the analogous O acceptor, with a −3.5 kcal/mol difference in ΔΔH25°C and −0.4 kcal/mol ΔΔG25°C (including an entropic penalty ΔΔS25°C of −10 cal/(mol K)). Thus sulfur is shown to be a favorable acceptor for bromine X-bonds, extending the application of this interaction for the design of inhibitors and biological materials.

Publisher URL: http://dx.doi.org/10.1021/acs.jpclett.7b01725

DOI: 10.1021/acs.jpclett.7b01725

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