Synthesis of photocaged 6-O-(2-nitrobenzyl) guanosine and 4-O-(2-nitrobenzyl) uridine triphosphates for photocontrol of the RNA transcription reaction

Publication date: Available online 21 September 2017
Source:Bioorganic & Medicinal Chemistry
Author(s): Kentaro Ohno, Daiki Sugiyama, Leo Takeshita, Takashi Kanamori, Yoshiaki Masaki, Mitsuo Sekine, Kohji Seio
6-O-(2-Nitrobenzyl)guanosine and 4-O-(2-nitrobenzyl)uridine triphosphates (^NBGTP, ^NBUTP) were synthesized, and their biochemical and photophysical properties were evaluated. We synthesized ^NBUTP using the canonical triphosphate synthesis method and ^NBGTP from 2′,3′-O-TBDMS guanosine via a triphosphate synthesis method by utilizing mild acidic desilylation conditions. Deprotection of the nitrobenzyl group in ^NBGTP and ^NBUTP proceeded within 60 s by UV irradiation at 365 nm. Experiments using ^NBGTP or ^NBUTP in T7-RNA transcription reactions showed that ^NBGTP could be useful for the photocontrol of transcription by UV irradiation.

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