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

• I which represents modified cytidine analogues bearing a secondary alcohol at position C-5 of cytosine. Additionally, a synthesis of 3,6-dihydrodeoxycytidine derivatives of general formula II is presented (Figure 1). We chose the known aldehyde 1 [29] (prepared from commercially available 2

• )acetylide, THF, −50 °C, lithium phenylacetylide, THF, −78 °C → −50 °C, vinylmagnesium bromide, THF, 0 °C) afforded 3,6-dihydrodeoxycytidine derivatives 8a–e as mixtures of diastereomers. In case of 8b the diastereomers were separated by HPLC. Products arising from addition of the organometallic reagents to