Synthesis of Nucleoside and Nucleotide Analogues by Cyclization of the Guanine Base with 1,1,3,3-Tetramethoxypropane.
Ting-Ting DengYi-Bing XieWen-Wu SunJie HuangTing-Ting HeJi-Kai LiuBin WuPublished in: Organic letters (2022)
3-(2-Deoxy-β-d-erythropentofuranosyl)pyrimido[1,2-<i>a</i>]purin-10(3<i>H</i>)-one (M<sub>1</sub>dG) is an endogenous DNA adduct in bacterial and mammalian cells that could be explored as a biomarker for oxidative stress. Nonetheless, the lack of an efficient methodology for the preparation of M<sub>1</sub>dG hampers the deep investigation of its biosynthesis and biorelevant processes. In this project, we aimed to address this issue by developing a highly efficient method to synthesize M<sub>1</sub>dG and its analogues. This method has wide functional group tolerance, as various guanine-based nucleosides and nucleotides are suitable for the reaction. Furthermore, large-scale and derivatization reactions were carried out to showcase the possibility for biochemists to study DNA damage and repair processes in the future.
Keyphrases
- highly efficient
- dna damage
- oxidative stress
- molecular docking
- ms ms
- ischemia reperfusion injury
- liquid chromatography tandem mass spectrometry
- high performance liquid chromatography
- current status
- structure activity relationship
- cell free
- diabetic rats
- gas chromatography mass spectrometry
- mass spectrometry
- liquid chromatography
- molecular dynamics simulations
- tandem mass spectrometry