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Schröder, Arne S.; Kotljarova, Olga; Parsa, Edris; Iwan, Katharina; Raddaoui, Nada; Carell, Thomas (2016): Synthesis of (R)-Configured 2 '-Fluorinated mC, hmC, fC, and caC Phosphoramidites and Oligonucleotides. In: Organic Letters, Vol. 18, Nr. 17: S. 4368-4371
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Investigation of the function of the new epigenetic bases requires the development of stabilized analogues that are stable during base excision repair (BER). Here we report the synthesis of 2'-(R)-fluorinated versions of the phosphoramidites of 5-methylcytosine (mC), 5-hydroxymethylcytosine (hmC), 5-formylcytosine (fC), and 5-carboxycytosine (caC). For oligonucleotides containing 2'-(R)-F-fdC, we show that these compounds cannot be cleaved by the main BER enzyme thymine-DNA glycosylase (TDG).