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Fluorinated DNA Bases as Probes of Electrostatic Effects in DNA Base Stacking
Author(s) -
Lai Jacob S.,
Qu Jin,
Kool Eric T.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352531
Subject(s) - stacking , dna , fluorine , base (topology) , chemistry , electrostatics , helix (gastropod) , nucleobase , base pair , static electricity , crystallography , chemical physics , organic chemistry , biochemistry , physics , biology , mathematical analysis , ecology , mathematics , quantum mechanics , snail
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.