Open AccessDirecting macromolecular conformation through halogen bonds
Author(s) -
Andrea Regier Voth,
Franklin A. Hays,
P Shing Ho
Publication year - 2007
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.0610531104
Subject(s) - bromine , hydrogen bond , macromolecule , halogen , chemistry , halogen bond , molecule , supramolecular chemistry , non covalent interactions , rational design , chlorine , crystallography , computational chemistry , nanotechnology , materials science , organic chemistry , biochemistry , alkyl
The halogen bond, a noncovalent interaction involving polarizable chlorine, bromine, or iodine molecular substituents, is now being exploited to control the assembly of small molecules in the design of supramolecular complexes and new materials. We demonstrate that a halogen bond formed between a brominated uracil and phosphate oxygen can be engineered to direct the conformation of a biological molecule, in this case to define the conformational isomer of a four-stranded DNA junction when placed in direct competition against a classic hydrogen bond. As a result, this bromine interaction is estimated to be ≈2–5 kcal/mol stronger than the analogous hydrogen bond in this environment, depending on the geometry of the halogen bond. This study helps to establish halogen bonding as a potential tool for the rational design and construction of molecular materials with DNA and other biological macromolecules.