Synthesis of photocaged6-O-(2-nitrobenzyl) guanosine and 4-O-(2-nitrobenzyl)uridine triphosphates for photocontrol of the RNA transcription reaction

6-O-(2-Nitrobenzyl) guanosine and 4-O-(2-nitrobenzyl) uridine triphosphates ((NB)GTP, (UTP)-U-NB) were synthesized, and their biochemical and photophysical properties were evaluated. We synthesized (UTP)-U-NB using the canonical triphosphate synthesis method and (NB)GTP from 2',3'-O-TBDMS guanosine via a triphosphate synthesis method by utilizing mild acidic desilylation conditions. Deprotection of the nitrobenzyl group in (NB)GTP and (UTP)-U-NB proceeded within 60 s by UV irradiation at 365 nm. Experiments using (NB)GTP or (UTP)-U-NB in T7-RNA transcription reactions showed that (NB)GTP could be useful for the photocontrol of transcription by UV irradiation. (C) 2017 Elsevier Ltd. All rights reserved.