Synthesis of (R)-Configured 2′-Fluorinated mC, hmC, fC, and caC Phosphoramidites and Oligonucleotides

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• 作者：Arne S. Schröder ; Olga Kotljarova ; Edris Parsa ; Katharina Iwan ; Nada Raddaoui ; Thomas Carell
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4368-4371
• 全文大小：404K
• 年卷期：0
• ISSN：1523-7052

文摘

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).