Fig. 4: Substrate scope of C-H alkylation of complex nucleotide substrates. | Nature Communications

Fig. 4: Substrate scope of C-H alkylation of complex nucleotide substrates.

From: Late-stage guanine C8–H alkylation of nucleosides, nucleotides, and oligonucleotides via photo-mediated Minisci reaction

Fig. 4

a C-H alkylation of dinucleotide and cyclic dinucleotide substrates. aGeneral condition: dinucleotides or nucleotides (1.0 equiv.), alkylboronic acid (4.0 equiv.), MesAcr (5 mol%), (NH4)2S2O8 (2.0 equiv.), TFA (1.0 equiv.) and catechol (1.0 equiv.) in MeCN: H2O (1: 1, 0.1 M) on 0.06 mmol scale; irradiated by 10 W blue LED at ~10 °C for 24 h; isolated yield. bNo TFA was used, and the reaction time was shortened to 5 hours. cRun on 0.04 mmol scale. b C-H alkylation of nucleotide substrates. dIrradiated by 36 W blue LED at r.t. for 16 h. eIrradiated by 85 W white light at r.t. for 16 h. 10 mM NH4HCO3 (aq.) was used instead of H2O, and No TFA was used. ei-PrB(OH)2 was used instead of EtB(OH)2 as C8-Et-GTP cannot be separated from GTP.

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