Literature DB >> 17625822

Tautomerism of uracil and 5-bromouracil in a microcosmic environment with water and metal ions. What roles do metal ions play?

Xingbang Hu1, Haoran Li, Lei Zhang, Shijun Han.   

Abstract

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.

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Year:  2007        PMID: 17625822     DOI: 10.1021/jp0709454

Source DB:  PubMed          Journal:  J Phys Chem B        ISSN: 1520-5207            Impact factor:   2.991


  3 in total

1.  Protonation preferentially stabilizes minor tautomers of the halouracils: IRMPD action spectroscopy and theoretical studies.

Authors:  K T Crampton; A I Rathur; Y-w Nei; G Berden; J Oomens; M T Rodgers
Journal:  J Am Soc Mass Spectrom       Date:  2012-07-21       Impact factor: 3.109

2.  The influence of isolated and penta-hydrated Zn2+ on some of the intramolecular proton-transfer processes of thymine: a quantum chemical study.

Authors:  Dejie Li; Ying Han; Huijuan Li; Ping Zhang; Qi Kang; Zhihua Li; Dazhong Shen
Journal:  RSC Adv       Date:  2018-03-20       Impact factor: 4.036

3.  Acid-base and metal ion binding properties of 2-thiocytidine in aqueous solution.

Authors:  Justyna Brasuń; Agnieszka Matera; Elzbieta Sochacka; Jolanta Swiatek-Kozlowska; Henryk Kozlowski; Bert P Operschall; Helmut Sigel
Journal:  J Biol Inorg Chem       Date:  2008-02-29       Impact factor: 3.358

  3 in total

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