Tautomerism of uracil and 5-bromouracil in a microcosmic environment with water and metal ions. What roles do metal ions play?
The base tautomerization processes of uracil/5-bromouracil were investigated in a microcosmic environment with both H2O and Na+ (W-M environment). It was found that uracil was more stable in the W-M environment than in the microcosmic environment with only water, which suggested that the metal ions and water work cooperated to maintain the classical nucleic acid bases. However, 5-bromouracil, a chemical mutagen, was found to be less stable than uracil in the W-M environment. Why the 5-bromouracil is easier to tautomerize and therefore induce gene mutation was explained to some extent. Further research revealed that the water molecule would assist the tautomerization in the W-M environment. However, the metal ions in different regions play absolutely opposite roles: in one region, the metal ions can prevent the base from tautomerizing, whereas in another region, the metal ion can assist the tautomerization process. Furthermore, from the viewpoint of ionization of the base, it seems BrU has a stronger tendency to lose the proton at N3, which is an intrinsic consequence of the bromine atom and is not affected by the metal cation.
Hu
Xingbang
X
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
Li
Haoran
H
Zhang
Lei
L
Han
Shijun
S
D001966:Bromine / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D013816:Thermodynamics; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D007477:Ions; D008670:Metals; D014867:Water; D014498:Uracil; D010100:Oxygen; D001966:Bromine