5VBJ

Sulfur as a bromine biomolecular halogen-bond acceptor

Summary for 5VBJ

• Entry DOI: 10.2210/pdb5vbj/pdb
• Descriptor: DNA (5'-D(*CP*CP*GP*AP*TP*(AS)P*(BRU)P*CP*GP*G)-3'), CALCIUM ION (3 entities in total)
• Functional Keywords: biophysics, bromine, dna, sulfur, halogen bonding, models, molecular, molecular conformation, uracil
• Biological source: synthetic construct
• Total number of polymer chains: 2
• Total formula weight: 6291.96

Authors

Ford, M.C.,Ho, P.S. (deposition date: 2017-03-29, release date: 2017-08-09, Last modification date: 2024-03-06)

Primary citation

Ford, M.C.,Saxton, M.,Ho, P.S.
Sulfur as an Acceptor to Bromine in Biomolecular Halogen Bonds.
J Phys Chem Lett, 8:4246-4252, 2017

PubMed Abstract: 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 ΔΔH and -0.4 kcal/mol ΔΔG (including an entropic penalty ΔΔS 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.

PubMed: 28796521
DOI: 10.1021/acs.jpclett.7b01725

Experimental method

X-RAY DIFFRACTION (1.944 Å)