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.

Department of Organic Chemistry Faculty of Science Charles University Hlavova 8 CZ 12843 Prague 2 Czech Republic

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nam 2 16000 Prague 6 Czech Republic

Laboratory of Microbial Genetics and Gene Expression Institute of Microbiology Czech Academy of Sciences Vídeňská 1083 CZ 14220 Prague 4 Czech Republic

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