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Products > TCI Topics Archives > TCI Topics 2014 >

The Sixth Nucleoside of the Genome, 5-hmdC

2'-Deoxy-5-(hydroxymethyl)cytidine (5-hmdC) and its base 5-hydroxymethylcytosine (5-hmC) were recently discovered as oxidation products of 2’-deoxy-5-methylcytidine (5-mdC) in mammalian DNA, particularly in stem cell DNA. 5-mdC, a C5-methylated form of 2'-deoxycytidine (dC), has been studied as an indicator of DNA methylation in epigenetics. On the other hand, the biological function of 5-hmdC is currently not clear, but it is assumed that in stem cells it might be an intermediate of an active de-methylation process. Detection of 5-hmdC in a genome has been investigated to elucidate its role.

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References

The Discovery of 5-Formylcytosine in Embryonic Stem Cell DNA
- T. Pfaffeneder, B. Hackner, M. Truß, M. Münzel, M. Müller, C. A. Deiml, C. Hagemeier, T. Carell, Angew. Chem. Int. Ed. 2011, 50, 7008.
5-Hydroxymethylcytosine, the Sixth Base of the Genome (Minireview)
- M. Münzel, D. Globisch, T. Carell, Angew. Chem. Int. Ed. 2011, 50, 6460.
5-Hydroxymethylcytosine Is Strongly Depleted in Human Cancers but Its Levels Do Not Correlate with IDH1 Mutations
- S.-G. Jin, Y. Jiang, R. Qiu, T. A. Rauch, Y. Wang, G. Schackert, D. Krex, Q. Lu, G. P. Pfeifer, Cancer Res. 2011, 71, 7360.
Determination of genomic 5-hydroxymethyl-2'-deoxycytidine in human DNA by capillary electrophoresis with laser-induced fluorescence
- A. M. Krais, Y. J. Park, C. Plass, H. H. Schmeiser, Epigenetics 2011, 6, 560.
Discrimination between 5-hydroxymethylcytosine and 5-methylcytosine in DNA by selective chemical labeling
- J. Hu, Y. Chen, X. Xu, F. Wu, X. Xing, Z. Xu, J. Xu, X. Weng, X. Zhou, Bioorg. Med. Chem. Lett. 2014, 24, 294.
Deamination, Oxidation, and C–C Bond Cleavage Reactivity of 5-Hydroxymethylcytosine, 5-Formylcytosine, and 5-Carboxycytosine
- S. Schiesser, T. Pfaffeneder, K. Sadeghian, B. Hackner, B. Steigenberger, A. S. Schröder, J. Steinbacher, G. Kashiwazaki, G. Höfner, K. T. Wanner, C. Ochsenfeld, T. Carell, J. Am. Chem. Soc. 2013, 135, 14593.