Structural studies of biologically interesting fluorinated nucleosides

FLUO 20

Joseph J. Barchi Jr., barchi@helix.nih.gov, Laboratory of Medicinal Chemistry, National Cancer Institute at Frederick, NIH, 376 Boyles Street, Bldg 376, Room 209, Frederick, MD 21702
The use of nucleosides and nucleoside analogues as therapeutic agents has a long and prosperous history in anticancer and antiviral drug discovery. Recently, several groups have synthesized nucleosides containing modified sugar ring scaffolds that bias the furanose conformation to assume either a North (A-DNA like) or South (B-DNA like) ring pucker. We have prepared several of these analogues that contain a fluorine atom in the ring and studied their structures with both NMR (1H and 19F) and ab initio calculations. We sought to define the precise roles played by the highly electronegative fluorine atoms in defining specific sugar conformations. The talk will highlight recent progress in this area and discuss the therapeutic consequences of fluorine substitution into nucleoside monomers and oligomers.
 

Fluorinated Heterocycles
1:30 PM-4:55 PM, Monday, 11 September 2006 San Francisco Marriott -- Salon 5, Oral

Division of Fluorine Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006