An oligodeoxyribonucleotide containing 5-formyl-2′-deoxycytidine (fC) at the CpG site forms a covalent complex with DNA cytosine-5 methyltransferases (DNMTs)

[Display omitted] 5-Methylcytosine (mC) is known to induce epigenetic changes. Ten-eleven translocation (TET) enzymes produce the further oxidized 5-substituted cytosine derivatives, 5-formylcytosine (fC) and 5-carboxylcytosine (caC). However, their roles are unclear thus far. Here, we synthesized o...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2016-11, Vol.26 (22), p.5395-5398
Hauptverfasser: Sato, Kousuke, Kawamoto, Kyoji, Shimamura, Shintaro, Ichikawa, Satoshi, Matsuda, Akira
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Sprache:eng
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Zusammenfassung:[Display omitted] 5-Methylcytosine (mC) is known to induce epigenetic changes. Ten-eleven translocation (TET) enzymes produce the further oxidized 5-substituted cytosine derivatives, 5-formylcytosine (fC) and 5-carboxylcytosine (caC). However, their roles are unclear thus far. Here, we synthesized oligodeoxyribonucleotides (ODNs) containing 5-formyl-2′-deoxycytidine and examined their interactions with DNA cytosine-5 methyltransferase (DNMT). We found that the ODN sequence containing fCpG formed a covalent complex with both bacterial and mouse recombinant DNMTs in the absence of any cofactors. The covalent bonding with DNMT suggests that the fCpG sequence in DNA may play a role in epigenetic regulation.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2016.10.040