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- W2406222724 abstract "The base-pairing interactions of promutagen- ic 06-methylguanine (06-MeGua) with cytosine and thymine in deuterated chloroform were investigated by 1H NMR spectros- copy. Nucleosides were derivatized at hydroxyl positions with triisopropylsilyl groups to obtain solubility in nonaqueous solvents and to prevent the ribose hydroxyls from forming hydrogen bonds. We were able to observe hydrogen-bonding interactions between nucleic acid bases in a solvent of low dielectric constant, a condition that approximates the hydro- phobic interior of the DNA helix. 06-MeGua was observed to form a hydrogen-bonded mispair with thymine. Whereas 06-MeGua did not form hydrogen bonds with cytosine (via usual, wobble, or unusual tautomeric structures), it did form a 1:1 hydrogen-bonded complex with protonated cytosine. The pairing of unprotonated cytosine in chloroform is thus consist- ent with the known preference of 06-MeGua for thymine over cytosine in polymerase reactions. In contrast, the pairing of protonated cytosine is consistent with the greater stability of oligonucleotide duplexes containing cytosine'06-MeGua as compared with thymine0O6-MeGua base pairs (Gaffney, B. L., Markey, L. A. & Jones, R. A. (1984) Biochemistry 23, 5686- 5691). Our observation that cytosine must be protonated in order to pair with 06-MeGua suggests that the cytosine0 6- MeGua base pair in DNA is stabilized by protonation of cytosine. Through this mechanism, methylation at the 06 position of guanine in double-stranded DNA could promote cross-strand deamination of cytosine (or 5-methylcytosine) to produce uracil (or thymine)." @default.
- W2406222724 created "2016-06-24" @default.
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- W2406222724 date "2016-01-01" @default.
- W2406222724 modified "2023-09-23" @default.
- W2406222724 title "Protonated base pairs explain the a properties of 06-methylguanine (hydrogen bonding/DNA structure/protonated cytosine/mutagenesi" @default.
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