Journal
CHEMICAL SCIENCE
Volume 6, Issue 5, Pages 3013-3017Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc00484e
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Funding
- National Basic Research Program of China (973 Program) [2012CB720600, 2012CB720603]
- National Science Foundation of China [91213302, 21432008, 91413109]
- National Grand Program on Key Infectious Disease [2012ZX10003002-014]
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N-6-Methyladenosine (m(6)A) represents a relatively abundant modification in eukaryotic RNA. Because m(6)A 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 m(6)A through the bicarbonate-activated peroxide system. Over the course of oxidation, we found a new mechanism in which N-6-hydroxymethyladenosine (hm(6)A), N-6-formyladenosine (f(6)A) and N-6-hydroperoxymethyladenosine (oxm(6)A) 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 m(6)A by reactive oxygen species at the nucleobase level and in RNA strands.
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