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.
Highlights
RNA shows about a hundred different post-transcriptionally modified nucleosides and most of them are in tRNA
Oxidation of 5-methylaminomethyl uridine Leads to Two Oxidation Products
5-methylaminomethyl modified ribonucleosides are present at the key position 34 in ASL in tRNAs, the present work investigated the oxidation of mnm U, since oxidative
Summary
RNA shows about a hundred different post-transcriptionally modified nucleosides and most of them are in tRNA. They are enzymatically synthesized and are located at specific sites. They play diverse and indispensable roles in the decoding of mRNA and in the gene regulation in all living organisms [1,2]. Modifications in the anticodon stem and loop (ASL) domain of tRNA are the most diverse and the most complex of all modifications in RNA. Uridine at the wobble anticodon position 34 of tRNAs is often modified with a methylene carbon on C5 of uracil with a variety of modifications such as 5-methylaminomethyl, 5-oxyacetic acid, 5-taurinomethyl. Modifications to position 34 uridines are crucial for the precise decoding of the genetic information and for the tuning of protein synthesis [4,7,8]
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