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

Autor:	Arne S. Schröder, Thomas Carell, Nada Raddaoui, Katharina Iwan, Olga Kotljarova, Edris Parsa
Rok vydání:	2016
Předmět:	chemistry.chemical_classification 010405 organic chemistry Oligonucleotide Chemistry Organic Chemistry Base excision repair 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Enzyme DNA glycosylase Epigenetics Physical and Theoretical Chemistry Function (biology)
Zdroj:	Organic Letters. 18:4368-4371
ISSN:	1523-7052 1523-7060
Popis:	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).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ac8547502f05b9f50d1600d00ecf3e51 https://doi.org/10.1021/acs.orglett.6b02110 Zobrazit plný text záznamu