Synthesis of 5'-terminal capped oligonucleotides using O-N phosphoryl migration of phosphoramidite derivatives.

Akihiro Ohkubo, Nobuhiro Tago, Akira Yokouchi, Yudai Nishino, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine

Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.

Organic letters 2012 Jan 6

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Trivalent phosphoramidite derivatives could be readily converted by reacting with 1-hydroxy-7-azabenzotriazole to phosphotriester intermediates; these intermediates reacted smoothly with phosphorylated compounds to give pyrophosphate derivatives. This new phosphorylation approach enabled a facile and rapid synthesis of 5'-adenylated DNA oligomers (A(5')ppDNA) on resins using a silyl-type linker. Our new approach could be applied to the synthesis of a 2'-OMe-RNA oligomer containing the 5'-terminal 2,2,7-trimethylguanosine cap structure. © 2011 American Chemical Society

Citation

Akihiro Ohkubo, Nobuhiro Tago, Akira Yokouchi, Yudai Nishino, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine. Synthesis of 5'-terminal capped oligonucleotides using O-N phosphoryl migration of phosphoramidite derivatives. Organic letters. 2012 Jan 6;14(1):10-3