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Development of novel boron-containing nucleotide analogues by using nucleoside H-boranophosphonate derivatives as precursors.

Research Project

Project/Area Number 20750127
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemistry related to living body
Research InstitutionThe University of Tokyo

Principal Investigator

OKA Natsuhisa  The University of Tokyo, 工学部, 准教授 (50401229)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords核酸 / ホウ素 / ホスホン酸 / DNA / ヌクレオシド / 核酸類縁体 / ボラノホスホン酸 / 核酸医薬 / ヌクレオチド / H-ボラノホスホン酸 / ボラノホスフェート / 次亜リン酸
Research Abstract

P-Boronated nucleotide analogues have attracted much attention as potential therapeutic agents against various diseases, such as cancer and AIDS. However, only a few kinds of P-boronated nucleotide analogues are currently available. In this project, we have developed a new P-boronated nucleotide analogue, which contains a BH_3 group and an H group on the phosphorus atom. In addition, we found that this nucleotide analogue (nucleoside H-boranophosphonate) works as a precursor of other P-boronated nucleotides including currently unavailable compounds by substituting the H group.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (54 results)

All 2010 2009 2008 Other

All Journal Article (24 results) (of which Peer Reviewed: 17 results) Presentation (21 results) Book (2 results) Remarks (3 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation.2010

    • Author(s)
      Matsumura, F.; Tatsumi, S.; Oka, N.; Wada, T.
    • Journal Title

      Carbohydr. Res. (in press)

    • Related Report
      2009 Annual Research Report 2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] 1, 2-Trans-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides.2010

    • Author(s)
      Sato, K.; Oka, N.; Fujita, S.; Matsumura, F.; Wada, T.
    • Journal Title

      J. Org. Chem. 75

      Pages: 2147-2156

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solid-phase synthesis of oligodeoxyribonucleotides without base protection utilizing O-selective reaction of oxazaphospholidine derivatives.2010

    • Author(s)
      Oka, N.; Maizuru, Y.; Shimizu, M.; Wada, T.
    • Journal Title

      Nucleosides Nucleotides Nucleic Acids 75

      Pages: 144-154

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] 1,2-Trans-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides.2010

    • Author(s)
      Sato, K.; Oka, N.; Fujita, S.; Matsumura, F.; Wada, T.
    • Journal Title

      J.Org. Chem. 75

      Pages: 2147-2156

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid-phase synthesis of oligodeoxyribonucleotides without base protection utilizing O-selective reaction of oxazaphospholidine derivatives.2010

    • Author(s)
      Oka, N.; Maizuru, Y.; Shimizu, M.; Wada, T.
    • Journal Title

      Nucleosides Nucleotides Nucleic Acids 29

      Pages: 144-154

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of tertiary silanes via optically pure 1, 3, 2-oxazasilolidine derivatives.2009

    • Author(s)
      Oka, N.; Nakamura, M.; Soeda, N.; Wada, T.
    • Journal Title

      J. Organomet. Chem. 694

      Pages: 2171-2178

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nucleoside H-boranophosphonates: a new class of boron-containing nucleotide analogues.2009

    • Author(s)
      Higashida, R.; Oka, N.; Kawanaka, T.; Wada, T.
    • Journal Title

      Chem. Commun.

      Pages: 2466-2468

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of oligoribonucleoside phosphorothioates by an oxazaphospholidine approach.2009

    • Author(s)
      Oka, N.; Kondo, T.; Fujiwara, S.; Maizuru, Y.; Wada, T.
    • Journal Title

      Org. Lett. 11

      Pages: 967-970

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled solid-phase synthesis of oligonucleoside H-phosphonates by an oxazaphospholidine approach.2009

    • Author(s)
      Iwamoto, N.; Oka, N.; Sato, T.; Wada, T.
    • Journal Title

      Angew. Chem. Int. Ed. 48

      Pages: 496-499

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chemical synthesis of nucleoside H-boranophosphonates and their application as precursors of P-modified nucleotide analogs.2009

    • Author(s)
      Oka, N.; Higashida, R.; Takayama, Y.; Ando, K.; Wada, T.
    • Journal Title

      Nucleic Acids Symp. Ser. 53

      Pages: 111-112

    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Journal Article] Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates via stereo-defined H-phosphonate intermediates.2009

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T.
    • Journal Title

      Nucleic Acids Symp. Ser. 53

      Pages: 9-10

    • Related Report
      2009 Final Research Report
  • [Journal Article] Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates viastereo-defined H-phosphonate intermediates.2009

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T.
    • Journal Title

      Nucleic Acids Symp. Ser. 53

      Pages: 9-10

    • Related Report
      2009 Annual Research Report
  • [Journal Article] Stereocontrolled synthesis of tertiary silanes via optically pure 1,3,2-oxazasilolidine derivatives.2009

    • Author(s)
      Oka, N.; Nakamura, M.; Soeda, N.; Wada, T.
    • Journal Title

      J.Organomet. Chem. 694

      Pages: 2171-2178

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of oligoribonucleoside phosphorothioates by an oxazaphospholidine approach2009

    • Author(s)
      Oka. N. ; Kondo, T. ; Fujiwara, S. ; Maizuru, Y.; Wada, T.
    • Journal Title

      Organic etters 11

      Pages: 967-970

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nucleoside H-boranophosphonates : a new class of boron-containing nucleotide analogues2009

    • Author(s)
      Higashida, R. ; Oka. N. ; Kawanaka, T. ; Wada, T.
    • Journal Title

      Chemical Communications ((印刷中)掲載確定)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units.2008

    • Author(s)
      Oka, N.; Yamamoto, M.; Sato, T.; Wada, T.
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 16031-16037

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of α-glycosyl phosphites and phosphoramidites via O-selective glycosylation of H-phosphonate derivatives.2008

    • Author(s)
      Matsumura, F.; Oka, N.; Wada, T.
    • Journal Title

      Org. Lett. 10

      Pages: 5297-5300

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of backbone-modified oligonucleotides via diastereopure H-phosphonate intermediates.2008

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T.
    • Journal Title

      Nucleic Acids Symp. Ser. 52

      Pages: 333-334

    • Related Report
      2009 Final Research Report
  • [Journal Article] Stereocontrolled synthesis of oligonucleoside phosphorothioates and PO/PS-chimeric oligonucleotides by using oxazaphospholidine derivatives.2008

    • Author(s)
      Oka, N.; Yamamoto, M.; Sato, T.; Wada, T.
    • Journal Title

      Nucleic Acids Symp. Ser. 52

      Pages: 335-336

    • Related Report
      2009 Final Research Report
  • [Journal Article] Stereoselective synthesis of α-glycosyl phosphites and phosphoramiditesvia O-selective alvcosvlation of H-phosohonate derivatives2008

    • Author(s)
      Matsumura, F. ; Oka. N. ; Wada, T.
    • Journal Title

      Organic Letters 10

      Pages: 5297-5300

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphor othioates using bicyclic oxazaphospholidine derivatives as monomer units2008

    • Author(s)
      Oka. N. ; Yamamoto, M. ; Sato, T ; Wada, T.
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 16031-16037

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled solid-phase synthesis of oligonucleosid a H-phosphonates by an oxazaphospholidine approach2008

    • Author(s)
      Iwamoto, N. ; Oka. N. ; Sato, T. ; Wada. T.
    • Journal Title

      Angewandte Chemie, International Edition 48

      Pages: 496-499

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of backbonemodified oligonucleotides viadiastereopure Hphosphonate intermediates2008

    • Author(s)
      Iwamoto, N. ; Oka, N. ; Wada, T.
    • Journal Title

      Nucleic Acids Symposium Series 52

      Pages: 333-334

    • Related Report
      2008 Annual Research Report
  • [Journal Article] Stereocontrolled synthesis of oligonucleoside phosphorothioates and PO/PS-chimeric oliaonucleotides by usina oxazaohospholidine derivatives2008

    • Author(s)
      Oka, N. ; Yamamoto, M. ; Sato, T. ; Wada, T.
    • Journal Title

      Nucleic Acids Symposium Series 52

      Pages: 335-336

    • Related Report
      2008 Annual Research Report
  • [Presentation] グリコシルボラノホスフェートを用いた新規グリコシル化反応の開発2010

    • Author(s)
      和田猛, 巽志朗, 松村史子, 岡夏央
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] リボヌクレオシドH-ボラノホスホネートの合成と性質2010

    • Author(s)
      日浦進吾, 東田廉平, 岡夏央, 和田猛
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates via stereo-defined H-phosphonate intermediates.2009

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T.
    • Organizer
      第6回国際核酸化学シンポジウム
    • Place of Presentation
      高山市民文化会館
    • Year and Date
      2009-09-29
    • Related Report
      2009 Final Research Report
  • [Presentation] Chemical synthesis of nucleoside H-boranophosphonates and their application as precursors of P-modified nucleotide analogs.2009

    • Author(s)
      Oka, N.; Higashida, R.; Takayama, Y.; Ando, K.; Wada, T.
    • Organizer
      第6回国際核酸化学シンポジウム
    • Place of Presentation
      高山市民文化会館
    • Year and Date
      2009-09-29
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates viastereo-defined H-phosphonate intermediates.2009

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T.
    • Organizer
      第6回国際核酸化学シンポジウム
    • Place of Presentation
      高山市民文化会館
    • Year and Date
      2009-09-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] オリゴ(α-D-グリコシルボラノホスフェート)の合成と天然型ホスホグリカンへの変換2009

    • Author(s)
      藤田正一, 岡夏央, 松村史子, 和田猛
    • Organizer
      第29回日本糖質学会年会
    • Place of Presentation
      飛騨・世界生活文化センター
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] グリコシルボラノホスフェート誘導体の立体選択的合成2009

    • Author(s)
      佐藤一樹, 岡夏央, 藤田正一, 松村史子, 和田猛
    • Organizer
      第29回日本糖質学会年会
    • Place of Presentation
      飛騨・世界生活文化センター
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] オリゴ(α-D-グリコシルボラノボスフェート)の合成2009

    • Author(s)
      藤田正一・岡夏央・松村史子・和田猛
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] グリコシルボラノホスフェート誘導体の立体選択的合成2009

    • Author(s)
      和田猛・佐藤一樹・岡夏央・藤田正一・松村史子
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] グリコシルボラノホスフェート誘導体の立体選択的合成2009

    • Author(s)
      和田猛・佐藤一樹・岡夏央・藤田正一・松村史子
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学(船橋)
    • Year and Date
      2009-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] オリゴ(α-D-グリコシルボラノホスフェート)の合成2009

    • Author(s)
      藤田正一・岡夏央・松村史子・和田猛
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学(船橋)
    • Year and Date
      2009-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] H-ホスホネートDNAの立体選択的合成と変換反応2009

    • Author(s)
      岩本直樹・岡夏央・和田猛
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学(船橋)
    • Year and Date
      2009-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] H-ホスホネートDNAの立体選択的合成と変換反応2009

    • Author(s)
      岩本直樹・岡夏央・和田猛
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] ボラノホスホネート型核酸類縁体の合成と性質2008

    • Author(s)
      東田廉平・川中俊秀・岡夏央・和田猛
    • Organizer
      第18回アンチセンスシンポジウム
    • Place of Presentation
      岐阜大学
    • Year and Date
      2008-11-17
    • Related Report
      2009 Final Research Report
  • [Presentation] ボラノホスホネート型核酸類縁体の合成と性質2008

    • Author(s)
      東田廉平・川中俊秀・岡夏央・和田猛
    • Organizer
      第18回アンチセンスシンポジウム
    • Place of Presentation
      岐阜大学医学部記念会館
    • Year and Date
      2008-11-17
    • Related Report
      2008 Annual Research Report
  • [Presentation] Stereocontrolled synthesis of oligonucleoside phosphorothioates and PO/PS-chimeric oligonucleotides by using oxazaphospholidine derivatives.2008

    • Author(s)
      Oka, N.; Yamamoto, M.; Sato, T.; Wada, T.
    • Organizer
      第18回International Roundtable on Nucleosides, Nucleotides, and Nucleic Acidsおよび第35回国際核酸化学シンポジウム合同シンポジウム
    • Place of Presentation
      京都大学
    • Year and Date
      2008-09-10
    • Related Report
      2009 Final Research Report
  • [Presentation] Stereocontrolled synthesis of backbone-modified oligonucleotides via diastereopure H-phosphonate intermediates.2008

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T.
    • Organizer
      第18回International Roundtable on Nucleosides, Nucleotides, and Nucleic Acidsおよび第35回国際核酸化学シンポジウム合同シンポジウム
    • Place of Presentation
      京都大学
    • Year and Date
      2008-09-10
    • Related Report
      2009 Final Research Report
  • [Presentation] Stereocontrolled synthesis of oligonucleoside phosphorothioates and PO/PSchimeric oligonucleotides by using oxazaphospholidine derivatives2008

    • Author(s)
      Oka. N. ; Yamamoto, M. ; Sato, T. ; Wada, T.
    • Organizer
      第18回International Roundtable on Nucleosides, Nucleotides, and Nucleic Acidsおよび第35回国際核酸化学シンポジウム合同シンポジウム
    • Place of Presentation
      京都大学百周年時計台記念館
    • Year and Date
      2008-09-10
    • Related Report
      2008 Annual Research Report
  • [Presentation] Stereocontrolled synthesis of backbonemodified oligonucleotides via diastereopure Hphosphonate intermediates2008

    • Author(s)
      Iwamoto, N ; Oka, N. ; Wada, T.
    • Organizer
      第18回International Roundtable on Nucleosides, Nucleotides, and Nucleic Acidsおよび第35回国際核酸化学シンポジウム合同シンポジウム
    • Place of Presentation
      京都大学百周年時計台記念館
    • Year and Date
      2008-09-10
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis of glycosyl boranophosphate derivatives and their applications as stable precursors of a variety of glycosyl phosphate analogs.2008

    • Author(s)
      Matsumura, F.; Oka, N.; Wada, T.
    • Organizer
      XXIV International Carbohydrate Symposium
    • Place of Presentation
      University of Oslo
    • Year and Date
      2008-07-28
    • Related Report
      2009 Final Research Report
  • [Presentation] Synthesis of glycosyl boranophosphate derivatives and their applications as stable precursors of a variety of glycosyl phosphate analogs2008

    • Author(s)
      Matsumura, F. ; Oka. N. ; Wada, T.
    • Organizer
      XXIV International Carbohydrate Symposium
    • Place of Presentation
      University of Oslo
    • Year and Date
      2008-07-28
    • Related Report
      2008 Annual Research Report
  • [Book] 複合糖質の化学と最新応用技術第3章糖-1-リン酸誘導体の化学合成2009

    • Author(s)
      岡夏央, 松村史子, 和田猛
    • Publisher
      シーエムシー出版
    • Related Report
      2009 Final Research Report
  • [Book] 複合糖質の化学と最新応用技術 第3章 糖-1-リン酸誘導体の化学合成2009

    • Author(s)
      岡夏央、松村史子、和田猛
    • Publisher
      シーエムシー出版
    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://apchem.gifu-u.ac.jp/~kinou1/

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://apchem.gifu-u.ac.jp/~kinoul/

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://park.itc.u-tokyo.ac.jp/moldes/index.html

    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 糖1-リン酸化合物の製造方法2008

    • Inventor(s)
      和田猛, 松村史子, 岡夏央
    • Industrial Property Rights Holder
      和田猛, 松村史子, 岡夏央
    • Filing Date
      2008-07-24
    • Related Report
      2009 Final Research Report
  • [Patent(Industrial Property Rights)] 糖ボラノホスフェート化合物及びその用途2008

    • Inventor(s)
      和田猛, 松村史子, 岡夏央
    • Industrial Property Rights Holder
      和田猛, 松村史子, 岡夏央
    • Filing Date
      2008-06-09
    • Related Report
      2009 Final Research Report
  • [Patent(Industrial Property Rights)] 糖ボラノホスフェート化合物及びその用途2008

    • Inventor(s)
      和田猛, 松村史子, 岡夏央
    • Industrial Property Rights Holder
      和田猛, 松村史子, 岡夏央
    • Industrial Property Number
      2008-150792
    • Filing Date
      2008-06-09
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 糖1-リン酸化合物の製造方法2008

    • Inventor(s)
      和田猛, 松村史子, 岡夏央
    • Industrial Property Rights Holder
      和田猛, 松村史子, 岡夏央
    • Industrial Property Number
      2008-190982
    • Filing Date
      2008-07-24
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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