title: An oligodeoxyribonucleotide containing 5-formyl-2'-deoxycytidine (fC) at the CpG site forms a covalent complex with DNA cytosine-5 methyltransferases (DNMTs).
abstract: 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.
authors: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
authors: Kousuke
authors: K
authors: Sato
authors: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
authors: Kyoji
authors: K
authors: Kawamoto
authors: Department of Molecular Microbiology and Immunology, Nagasaki University School of Medicine, Nagasaki 852-8501, Japan.
authors: Shintaro
authors: S
authors: Shimamura
authors: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
authors: Satoshi
authors: S
authors: Ichikawa
authors: Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
authors: Akira
authors: A
authors: Matsuda
mesh_terms: D000818:Animals; D001483:Base Sequence; D004248:DNA (Cytosine-5-)-Methyltransferases / Q000378:metabolism*; D019175:DNA Methylation; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D044135:Haemophilus parainfluenzae / Q000201:enzymology; D051379:Mice; D062105:Molecular Docking Simulation; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000378:metabolism*; D011994:Recombinant Proteins / Q000378:metabolism
chemical_list: C402104:5-formyl-2'-deoxycytidine; D009838:Oligodeoxyribonucleotides; D011994:Recombinant Proteins; D003841:Deoxycytidine; D004248:DNA (Cytosine-5-)-Methyltransferases
keywords: 5-Formyl-2′-deoxycytidine; Covalent bond; DNA methyltransferase; Epigenetic; Nucleic acids