Effect of 4'-alkyl substituted nucleosides on DNA charge transport

ORGN 308

Frank Onyemauwa, School of Chemistry and Biochemistry, Georgia Institute of Technology, 770 State Street, Atlanta, GA 30332 and Gary B. Schuster, Department of Chemistry and Biochemistry, Georgia Institute of Technology, 770 State Street, Atlanta, GA 30332.
DNA damage is caused by loss of an electron from a base to form a radical cation. The radical cation (‘hole’) migrates further across the bases and can cause mutations of the DNA. Detailed structural analysis of DNA oligonucleotides indicates the presence of tightly bound water molecules in the minor groove of the duplex. The effect of elimination of water from the minor groove on radical cation charge transport and reaction by substitution with 4’-alkyl modified nucleotides into the DNA duplexes is investigated. The radical cation is introduced into the DNA duplex by irradiation of a covalently linked anthraquinone derivative with a UV-light at 350 nm. Preliminary results indicate that the presence of water molecules in the minor groove affects radical cation reaction.