Guanine 8-Oxy-7,8-dihydrodeoxyguanine

(may mispair with adenine)

4 17.21 Oxidative radicals convert guanine into 8-oxy-7,8-dihydrodeoxyguanine, which frequently mispairs with adenine instead of cytosine, producing a CG : TA transversion.

about the same size as a nucleotide (< Figure 17.22a). They produce mutations by sandwiching themselves (intercalating) between adjacent bases in DNA, distorting the three-dimensional structure of the helix and causing sin-gle-nucleotide insertions and deletions in replication (< Figure 17.22b). These insertions and deletions frequently produce frameshift mutations (which change all amino acids downstream of the mutation), and so the mutagenic effects of intercalating agents are often severe. Because intercalating agents generate both additions and deletions, they can reverse the effects of their own mutations.


Chemicals can produce mutations by a number of mechanisms. Base analogs are inserted into DNA and frequently pair with the wrong base. Alkylating agents, deaminating chemicals, hydroxylamine, and oxidative radicals change the structure of DNA bases, thereby altering their pairing properties. Intercalating agents wedge between the bases and cause single-base insertions and deletions in replication.

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