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Biomolecules 2018, 8(4), 145; https://doi.org/10.3390/biom8040145

Oxidation of 5-methylaminomethyl uridine (mnm5U) by Oxone Leads to Aldonitrone Derivatives

1
CNRS, Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse CEDEX4, France
2
Université de Toulouse, Université Paul Sabatier, UPS, 31330 Toulouse, France
3
Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
*
Author to whom correspondence should be addressed.
Received: 12 October 2018 / Revised: 6 November 2018 / Accepted: 8 November 2018 / Published: 14 November 2018
(This article belongs to the Collection RNA Modifications)
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Abstract

Oxidative RNA damage is linked to cell dysfunction and diseases. The present work focuses on the in vitro oxidation of 5-methylaminomethyl uridine (mnm5U), which belongs to the numerous post-transcriptional modifications that are found in tRNA. The reaction of oxone with mnm5U in water at pH 7.5 leads to two aldonitrone derivatives. They form by two oxidation steps and one dehydration step. Therefore, the potential oxidation products of mnm5U in vivo may not be only aldonitrones, but also hydroxylamine and imine derivatives (which may be chemically more reactive). Irradiation of aldonitrone leads to unstable oxaziridine derivatives that are susceptible to isomerization to amide or to hydrolysis to aldehyde derivative. View Full-Text
Keywords: RNA oxidation; aldonitone; oxaziridine; KHSO5; water solvent RNA oxidation; aldonitone; oxaziridine; KHSO5; water solvent
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Zhou, Q.; Vu Ngoc, B.T.; Leszczynska, G.; Stigliani, J.-L.; Pratviel, G. Oxidation of 5-methylaminomethyl uridine (mnm5U) by Oxone Leads to Aldonitrone Derivatives. Biomolecules 2018, 8, 145.

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