Development of artificial aminoacylated tRNA with high efficiency of turnover

• Project/Area Number: 22750146
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemistry related to living body
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: OHKUBO Akihiro 東京工業大学, 大学院・生命理工学研究科, 助教 (60376960)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2010: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: RNA合成 / アミノアシルtRNA / ホスホロアミダイト法 / アミノ酸 / 固相合成

Research Abstract

In this study we could synthesize base-labile aminoacylated RNA oligonucleotides using N-unprotected 5'-phosphoramidite RNA units on the nucleoside-loaded polymer supports via a silyl linker which can be cleaved under neutral conditions. These results have prompted us to study the property of the RNA complexes between the aminoasylated RNAs and corresponding 5'-long RNAs. These additional studies are now underway.

Research Products

• [Journal Article] Formation of new base pairs between inosine and 5-methyl-2-thiocytidine derivatives (2012)
  • Author(s): A. Ohkubo, Y. Nishino, Y. Ito, H. Tsunoda, K. Seio, and M. Sekine
  • Journal Title: Org. Biomol. Chem. Volume: 10 Pages: 2008-2010
• [Journal Article] Development of an efficient method for phosphorodiamidate bond formation by using inorganic salts. (2012)
  • Author(s): T. Harakawa, H. Tsunoda, A. Ohkubo, K. Seio, and M. Sekine
  • Journal Title: Bioorg. Med. Chem. Lett Volume: 22 Pages: 1445-1447
• [Journal Article] Synthesis of 5'-Terminal Capped Oligonucleotide using O. N Phosphoryl Migration of Phosphoramidite Derivatives (2012)
  • Author(s): A. Ohkubo, N. Tago, A. Yokouchi, Y. Nishino, K. Yamada, H. Tsunoda, K. Seio, M. Sekine
  • Journal Title: Org. Lett. Volume: 14 Pages: 10-13
• [Journal Article] Short-RNA selective binding of oligonucleotides modified using adenosine and guanosine derivatives that possess cyclohexyl phosphates as substituents (2012)
  • Author(s): K. Seio, S. Kurohagi, E. Kodama, H. Tsunoda, A. Ohkubo and M. Sekine
  • Journal Title: Org. Biomol. Chem. Volume: 10 Pages: 994-1006
• [Journal Article] DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes (2012)
  • Author(s): T. Kanamori, Y. Masaki, M. Mizuta, H. Tsunoda, A. Ohkubo, M. Sekine, K. Seio
  • Journal Title: Org. Biomol. Chem. Volume: 10 Pages: 1007-1013
• [Journal Article] Formation of New Base Pairs between Inosine and 5-Methyl-2-thiocytidine Derivatives (2012)
  • Author(s): Ohkubo, A.; Nishino, Y.; Ito, Y.; Tsunoda, H.; Seio, K.; Sekine
  • Journal Title: Org.Biomol.Chem. Volume: 10 Issue: 10 Pages: 2008-2010
  • DOI: 10.1039/c2ob06641f
  • Peer Reviewed
• [Journal Article] Synthesis of 5'-Terminal Capped Oligonucleotide using O-N Phosphoryi Migration of Phosphoramidite Derivatives (2012)
  • Author(s): A.Ohkubo, N.Tago, A.Yokouchi, Y.Nishino, K.Yamada, H.Tsunoda, K.Seio, M.Sekine
  • Journal Title: Org.Lett. Volume: 14 Pages: 10-13
  • Peer Reviewed
• [Journal Article] Stable triplex formation using the strong stacking effect of consecutive thionucleoside moieties (2011)
  • Author(s): Y. Ito, Y. Noma, Y. Kakishima, Y. Masaki, H. Tsunoda, K. Seio, M. Sekine
  • Journal Title: Chem. Comm Volume: 47 Pages: 12556-12558
• [Journal Article] Biochemical behavior of N-oxidized cytosine and adenine bases in DNA polymerase-mediated primer extension reactions (2011)
  • Author(s): H. Tsunoda, T. Kudo, Y. Masaki, A. Ohkubo, K. Seio, M. Sekine
  • Journal Title: Nucleic Acids Res Volume: 39 Pages: 2995-3004
• [Journal Article] Synthesis of 2'-O-[ 2-(N-Methylcarbamoyl) ethyl] ribon ucleosides Using Oxa-Michael Reaction and Chemical and Biological Properties of Oligonucleotide Derivatives Incorporating These Modified Ribonucleosides (2011)
  • Author(s): Y. Takeshi, N. Okaniwa, H. Saneyoshi, A. Ohkubo, K. Seio, T. Nagata, Y. Aoki, S. Takeda, M. Sekine
  • Journal Title: J. Org. Chem Volume: 76 Pages: 3042-3053
• [Journal Article] Synthesis and triplex-forming properties of oligonucleotides containing thio-substituted C-nucleoside 4-thiopseudoisocytidine (2011)
  • Author(s): S. Cao, I. Okamoto, H. Tsunoda, A. Ohkubo, K. Seio, M. Sekine
  • Journal Title: Tetrahedron Lett. Volume: 52 Pages: 407-410
• [Journal Article] Synthesis and hybridization properties of 2'-O-methylated oligoribonucleotides incorporating 2'-O-naphthyluridines (2011)
  • Author(s): M. Sekine, Y. Oeda, Y. Iijima, H. Taguchi, A. Ohkubo, K. Seio
  • Journal Title: Org. Biomol. Chem Volume: 9 Pages: 210-218
• [Journal Article] Stable triplx formation using the strong stacking effect of consecutive thionucleoside moieties (2011)
  • Author(s): A.Ohkubo, Y.Nishino, A.Yokouchi, Y.Ito, Y.Noma, Y.Kakishima, Y.Masaki, H.Tsunoda, K.Seio, M.Sekine
  • Journal Title: Chem.Comm. Volume: 47 Issue: 46 Pages: 12556-12558
  • DOI: 10.1039/c1cc14339e
  • Peer Reviewed
• [Journal Article] Synthesis of oligodeoxynucleotides using fully protected deoxynucleoside 3'-phosphoramidite building blocks and base recognition of oligodeoxynucleotides incorporating N3-cyano-ethylthymine (2010)
  • Author(s): H. Tsunoda, T. Kudo, A. Ohkubo, K. Seio, M. Sekine
  • Journal Title: Molecules Volume: 15 Pages: 7509-7531
• [Journal Article] Insights into the DNA stabilizing contributions of a bicyclic cytosine analogue : crystal structures of DNA duplexes containing 7, 8-dihydropyrido[ 2, 3-d] pyrimidin-2-one. E. C. M. Juan (2010)
  • Author(s): S. Shimizu, X. Ma, T. Kurose, T. Haraguchi, F. Zhang, M. Tsunoda, A. Ohkubo, M. Sekine, T. Shibata, C. L. Millington, D. M. Williams, A. Takenaka
  • Journal Title: Nucleic Acids Res Volume: 38 Pages: 6737-6745
• [Journal Article] Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions (2010)
  • Author(s): A.Ohkubo, Y.Kuwayama, Y.Nishino, H.Tsunoda, K.Seio, M.Sekine
  • Journal Title: Organic Letters Volume: 12 Pages: 2496-2499
  • Peer Reviewed
• [Journal Article] Linear relationship between deformability and thermal stability of 2'-O-modified RNA hetero duplexes (2010)
  • Author(s): Y.Masaki, H.A.Ohkubo, K.Seio, M.Sekine
  • Journal Title: The Journal of Physical Chemistry B Volume: 114 Pages: 567-572
  • Peer Reviewed
• [Journal Article] Synthesis and hybridization properties of oligonucleotides incorporating Bi- and Tri-cyclic cytosine derivatives (2010)
  • Author(s): A.Ohkubo, T.Sakaue, H.Tsunoda, K.Seio, M.Sekine
  • Journal Title: Chemistry Letters Volume: 39 Pages: 726-727
  • Peer Reviewed
• [Journal Article] Synthesis and properties of cationic 2'-O-[ N-(4-aminobutyl) carbamoyl] modified oligonucleotides.
  • Author(s): K. Seio, M. Tokugawa, T. Kanamori, H. Tsunoda, A. Ohkubo, M. Sekine
  • Journal Title: Bioorg. Med. Chem. Lett. Volume: (in press)
• [Presentation] Synthesis and properties of oligonucleotides having 5'-terminal 2, 2, 7-trimethylguanosine cap analogues (2011)
  • Author(s): Akihiro Ohkubo, Akira Yokouchi, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
  • Organizer: Sixth Cambridge Symposium on Nucleic Acids Chemistry and Biology
  • Place of Presentation: Cambridge, UK
  • Year and Date: 2011-09-05
• [Presentation] Synthesis and Properties of Oligonucleotides having 5'-terminal 2, 2, 7-trimethylguanosine cap Analogues (2011)
  • Author(s): Akihiro Ohkubo, Akira Yokouchi, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
  • Organizer: 7th Annual Meeting of the Oligonucleotide Therapeutics Society
  • Place of Presentation: The Royal Library, Copenhagen, Denmark
• [Presentation] Synthesis and Properties of Oligonucleotides having 5'-terminal 2, 2, 7-trimethylguanosine cap Analogues 6th Cambridge Symposium on Nucleic Acids Chemistry and Biology (2011)
  • Author(s): Akihiro Ohkubo, Akira Yokouchi, Ken Yamada, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
  • Organizer: Queens' College
  • Place of Presentation: Cambridge, UK
• [Presentation] Synthesis and triplex formation of RNAs containing 8-thioxoadenine and 2-thiopyrimidine RNA2011 (2011)
  • Author(s): Akihiro Ohkubo, Yu Ito, Yudai Nishino, Akira Yokouchi, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
  • Organizer: the 16th Annual Meeting of the RNA Society and The RNA Society of Japan 13th Annual Meeting
  • Place of Presentation: 国立京都国際会館
• [Presentation] Synthesis and Properties of Oligonucleotides Having 5'-Terminal 2, 2, 7-Trimethylguanosine cap Analogues RNA2011 (2011)
  • Author(s): Akira Yokouchi, Ken Yamada, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine.
  • Organizer: the 16th Annual Meeting of the RNA Society and The RNA Society of Japan 13th Annual Meeting
  • Place of Presentation: 国立京都国際会館
• [Presentation] 塩基性条件下不安定な機能性RNAの新規合成法の開発 (2010)
  • Author(s): 大窪章寛、角田浩佑、清尾康志、関根光雄
  • Organizer: 第98回有機合成シンポジウム
  • Place of Presentation: 早稲田大学
  • Year and Date: 2010-11-05
• [Presentation] Synthesis and triplex formation of oligonucleotides containing 8-thioxoadenine 2-thiopyrimidine (2010)
  • Author(s): A.Ohkubo, Y.Nishino, Y.Kakishima, H.Tsunoda, K.Seio, M.Sekine
  • Organizer: XIX International Round Table on Nucleosides, Nucleotides and Nucleic Acids
  • Place of Presentation: Lyon (France)
  • Year and Date: 2010-09-01
• [Presentation] SYNTHESIS AND TRIPLEX FORMING OF OLIGONUCLEOTIDES CONTAINING 8-THIOXOADENINE AND 2-THIOPYRIMIDINE IRT 2010-XIX (2010)
  • Author(s): Akihiro Ohkubo, Yudai Nishino, Yuki Kakishima, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
  • Organizer: International Round Table on Nucleosides, Nucleotides and Nucleic Acids
  • Place of Presentation: Batiment CPE(Rue Victor Grignard), Universite Claude Bernard Lyon 1, France
• [Presentation] 2-チオピリミジンおよび8-チオキソプリンを含む修飾RANの三 (2010)
  • Author(s): 大窪章寛、西野雄大、柿島祐樹、正木慶昭、角田浩佑、清尾康志、関根光雄
  • Organizer: 重鎖形成能第12回日本RNA学会年会
  • Place of Presentation: 一橋記念講堂:学術総合センター
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  • URL: http://www.skn.bio.titech.ac.jp/