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Oxidative Damage on RNA Nucleobases

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Chemical Biology of Nucleic Acids

Part of the book series: RNA Technologies ((RNATECHN))

Abstract

Oxidatively damaged RNA has recently gathered more attention and has been closely related to different neurodegenerative diseases. The principles of oxidative stress and its influence on nucleic acids are reported. In contrast to DNA oxidative lesions of RNA have been scarcely described in the literature so far. These known stable RNA base modifications which arise under oxidative stress are reviewed here with regard to their biophysical properties and their potential mutagenicity. Furthermore the possible mechanisms of how cells deal with oxidized RNA are discussed. Posttranscriptional RNA modifications and the oxidation of RNA as an early event in several neurodegenerative diseases are not in the scope of this review.

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Notes

  1. 1.

    The melting curves for the matched case 5-HO-rC/G in RNA duplexes and RNA/DNA heteroduplexes show two distinct changes in hyperchromicity: the higher T m is close to the matched case whereas the lower T m is close to the mismatched case. This phenomenon is not yet fully understood and still under investigation.

  2. 2.

    The published findings confirm our earlier observations that the previously used 6O,7N-bis(dimethylcarbamyl) protected phosphoramidite of 8-oxo-rG is not fully deprotectable once incorporated into RNA. The authors here used a 6O,7N-bis(diphenylcarbamyl)-protected while we used an 6O,7N-unprotected phosphoramidite of 8-oxo-rG (unpublished results). Both phosphoramidites were fully deprotectable as confirmed by mass spectrometry. The T m values measured by Koga et al. correspond nicely to our findings (Table 1).

  3. 3.

    AMV-RT: avian myeloblastosis virus reverse transcriptase; MMLV-RT: moloney murine leukemia virus reverse transcriptase; HIV1-RT: human immunodeficiency virus type 1 reverse transcriptase; RAV2-RT: Rous-associated virus-2 reverse transcriptase.

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Acknowledgments

The authors wish to thank Dr. Alessandro Calabretta for the contribution of T m data for Table 1.

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  1. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012, Bern, Switzerland

    Pascal A. Küpfer & Christian J. Leumann

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  1. Institute of Chemistry/Biochemistry, Free University Berlin, Berlin, Germany

    Volker A. Erdmann

  2. Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan, Poland

    Wojciech T. Markiewicz

  3. Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan, Poland

    Jan Barciszewski

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Küpfer, P.A., Leumann, C.J. (2014). Oxidative Damage on RNA Nucleobases. In: Erdmann, V., Markiewicz, W., Barciszewski, J. (eds) Chemical Biology of Nucleic Acids. RNA Technologies. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-54452-1_5

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