Photocaged 5-(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA

0535556 - ÚOCHB 2021 RIV US eng J - Journal Article
Chakrapani, Aswathi - Vaňková Hausnerová, Viola - Ruiz-Larrabeiti, Olatz - Pohl, Radek - Krásný, Libor - Hocek, Michal
Photocaged 5-(Hydroxymethyl)pyrimidine Nucleoside Phosphoramidites for Specific Photoactivatable Epigenetic Labeling of DNA.
Organic Letters. Roč. 22, č. 22 (2020), s. 9081-9085. ISSN 1523-7060. E-ISSN 1523-7052
R&D Projects: GA MŠMT(CZ) EF16_019/0000729; GA ČR(CZ) GX20-00885X; GA ČR(CZ) GA20-12109S
Grant - others:AV ČR(CZ) Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963 ; RVO:61388971
Keywords : nucleosides * epigenetic nucleobases * oligonucleotides
OECD category: Organic chemistry; Microbiology (MBU-M)
Impact factor: 6.005, year: 2020
Method of publishing: Open access
https://doi.org/10.1021/acs.orglett.0c03462

5-Hydroxymethylcytosine and uracil are epigenetic nucleobases, but their biological roles are still unclear. We present the synthesis of 2-nitrobenzyl photocaged 5-hydroxymethyl-2′-deoxycytidine and uridine 3′-O-phosphoramidites and their use in automated solid-phase synthesis of oligonucleotides (ONs) modified at specific positions. The ONs were used as primers for PCR to construct DNA templates modified in the promoter region that allowed switching of transcription through photochemical uncaging.
Permanent Link: http://hdl.handle.net/11104/0313624