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

Schröder, Arne S.; Kotljarova, Olga; Parsa, Edris; Iwan, Katharina; Raddaoui, Nada and Carell, Thomas (2016): Synthesis of (R)-Configured 2 '-Fluorinated mC, hmC, fC, and caC Phosphoramidites and Oligonucleotides. In: Organic Letters, Vol. 18, No. 17: pp. 4368-4371

Abstract

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).

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English