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Fluorinated DNA Bases as Probes of Electrostatic Effects in DNA Base Stacking


  • This work was supported in part by the U.S. National Institutes of Health (GM52956/EB002059).


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Stacking the deck: A series of aromatic fluorinated nucleosides (the electrostatic surface potentials are depicted) was used to probe electrostatic effects in the stacking of DNA bases in water. Although increasing fluorine substitution (from zero through five) generally increases stacking ability, a new tetrafluorinated analogue is, surprisingly, the strongest helix stabilizer, while the pentafluorinated base is the weakest.

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