Synthesis of novel derivatives of 5-hydroxymethylcytosine and 5-formylcytosine as tools for epigenetics

• Anna Chentsova,
• Era Kapourani and
• Athanassios Giannis

Beilstein J. Org. Chem. 2014, 10, 7–11, doi:10.3762/bjoc.10.2

• (5hmC) and 5-formylcytosine (5fC) derivatives that can be used as tools in the emerging field of epigenetics for deciphering chemical biology of TET-mediated processes. Keywords: 3,6-dihydrodeoxycytidine derivatives; DNA demethylation; epigenetics; 5-hydroxymethylcytosine (5hmC) derivatives; TET

• is a densely studied field, its reverse process has not yet been deciphered. In trying to understand DNA demethylation several mechanisms involving new cytosine-modified bases as intermediates have been proposed (Scheme 1). (1) The most widely accepted pathway includes iterative oxidation of 5mC

• to play a decisive role in their self-renewal process [27]. Interestingly, the levels of 5hmC in several cancer types are strongly reduced relative to the corresponding normal tissue around the tumor [28]. To gain deeper insights into the chemical biology of DNA demethylation pathways further