Among nucleic acid modifications, pseudouridine (Ψ), the 5-ribosyl isomer of uridine(U) is the most abundant and is found in all domains of life and all types of RNA. There is evidence that RNA oxidation is a major player in the pathogenesis of Alzheimer’s disease (AD)and other neurodegenerative disorders. In addition, a correlation has been observed between high urinary levels of pseudouridine and oxidative stress in AD. In order to develop methods to qualitatively and quantitatively study the role that modified nucleic acids such as pseudouridine play in oxidative stress, methods are needed to facilitate the routine synthesis of oxidized pseudouridine damaged products and to analyze their degradation products. Here we present the synthesis of a radical precursor to investigate the fate of RNA damage emanating from hydrogen atom abstraction at the C5’ of pseudouridine. The precursor was photochemically converted to the C5’-radical and the resulting products were identified using LCMS and NMR.

Oxidation of RNA at naturally occurring modifications

2019 Fall National Meeting

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