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Synthesis of a DNA Promoter Segment Containing All Four Epigenetic Nucleosides: 5-Methyl-, 5-Hydroxymethyl-, 5-Formyl-, and 5-Carboxy-2′-Deoxycytidine


  • We thank the Deutsche Forschungsgemeinschaft (SFB749 and SFB646) for financial support. Additional support from the Fonds der Chemischen Industrie (predoctoral fellowships for A.S.S, S.S., T.P.) and two excellence clusters (CiPSM, EXC114) is acknowledged.


A 5-formyl-2′-deoxycytidine (fdC) phosphoramidite building block that enables the synthesis of fdC-containing DNA with excellent purity and yield has been developed. In combination with phosphoramidites for 5-methyl-dC, 5-hydroxymethyl-dC, and carboxy-dC, it was possible to prepare a segment of the OCT-4 promoter that contains all four epigenetic bases. Because of the enormous interest in these new epigenetic bases, the ability to insert all four of them into DNA should be of great value for the scientific community.

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