Student Research - Biochemistry and Molecular Biology
Jennifer Carman
Synthesis of 9-deaza-2'-deoxyguanosine, an analogue of 8-oxo-2'-deoxyguanosine
Abstract: The DNA base 2'-deoxyguanosine (dG) is susceptible to oxidation by reactive oxygen species that are formed in cells during biological processes as well as exposure to radiation. This oxidation causes the formation of the modified nucleotide 8-oxo-2'-deoxyguanosine (OdG). OdG can form base pairs with both dC and dA, whereas unmodified dG forms base pairs with only dC. Forming a base pair with dA can lead to dG to dT transverions, explaining how OdG is linked to aging and diseases such as cancer. OdG differs from dG at both the N7 and C8 positions. Analogs of OdG differing from OdG in only one position allows for the study of more specific reasons for OdG forming the base pairs that it does. The analogue 9-deaza-2'deoxyguanosine was synthesized to study the importance of the hydrogen bonding of N7-hydrogen without the presence of the C8-oxygen on OdG. This analogue will be used in biochemical studies in order to better understand its base pairing as well as recognition by repair enzymes.
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