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Issue 5, 2015
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N6-Hydroperoxymethyladenosine: a new intermediate of chemical oxidation of N6-methyladenosine mediated by bicarbonate-activated hydrogen peroxide

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Abstract

N 6-Methyladenosine (m6A) represents a relatively abundant modification in eukaryotic RNA. Because m6A has similar properties to adenosine and a low reactivity, limited research has been focused on this nucleoside. In this study, we revealed an important intermediate in the oxidation of m6A through the bicarbonate-activated peroxide system. Over the course of oxidation, we found a new mechanism in which N6-hydroxymethyladenosine (hm6A), N6-formyladenosine (f6A) and N6-hydroperoxymethyladenosine (oxm6A) were intermediate products, and adenosine was the final product. In this study, oxm6A was isolated using HPLC and characterized by mass spectrometry, NMR and diphenyl-1-pyrenylphosphine (DPPP) fluorescence detection. This study provides a new modified nucleoside and demonstrates oxidative demethylation of m6A by reactive oxygen species at the nucleobase level and in RNA strands.

Graphical abstract: N 6-Hydroperoxymethyladenosine: a new intermediate of chemical oxidation of N6-methyladenosine mediated by bicarbonate-activated hydrogen peroxide

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Article information


Submitted
09 Feb 2015
Accepted
10 Mar 2015
First published
11 Mar 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 3013-3017
Article type
Edge Article

N 6-Hydroperoxymethyladenosine: a new intermediate of chemical oxidation of N6-methyladenosine mediated by bicarbonate-activated hydrogen peroxide

J. Wu, H. Xiao, T. Wang, T. Hong, B. Fu, D. Bai, Z. He, S. Peng, X. Xing, J. Hu, P. Guo and X. Zhou, Chem. Sci., 2015, 6, 3013
DOI: 10.1039/C5SC00484E

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