ORGN 399 |
| When exposed to reactive oxygen species, 2'-deoxyguanosine (dG) can be oxidized to form the damaged nucleotide 8-oxo-2'-deoxyguanosine (OdG). OdG can form base pairs with both dC and dA, whereas unmodified dG forms base pairs only with dC. Forming a base pair with dA can lead to dG to dT transverions, possibly explaining why OdG has been linked to aging and cancer. OdG differs from dG at the N7 and C8 positions, both of which are thought to contribute to the promiscuous base paring of OdG. To gain further insight into the exact role of the N7 and C8 positions in OdG base pairing, the OdG analogue 9-deaza-2'-deoxyguanosine (CdG), which retains an N7-hydrogen (similar to OdG) but lacks a C8-oxygen (dissimilar to OdG), was synthesized. CdG then was incorporated into an eleven-nucleotide long oligonucleotide and tested for its stability in base pairs with dC and dA. |
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |