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Development of a method for the synthesis of biosynthetic intermediates of nucleic acids via phosphorylation of carbonyl group

Research Project

Project/Area Number 26410175
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bio-related chemistry
Research InstitutionGifu University

Principal Investigator

OKA Natsuhisa  岐阜大学, 工学部, 准教授 (50401229)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords核酸の生合成 / カルボニル基のリン酸化 / ヌクレオチド / 酵素応答性分子 / イノシン / 蛍光標識化 / アデニロコハク酸 / リン酸 / 酵素反応中間体 / 蛍光プローブ / 抗がん剤 / チオリン酸 / 生合成 / グアニン一リン酸 / ホスホロアミダイト / 生合成中間体 / イノシン6-リン酸
Outline of Final Research Achievements

This study aimed to develop a novel method for the synthesis of biosynthetic intermediates of nucleic acids and their chemically modified analogs. In order to achieve this goal, our original non-nucleophilic acidic activator, N-(cyanomethyl)dimethylammonium triflate (CMMT) was applied to the phosphitylation of carbonyl oxygen, finally enabling us to synthesize inosine 6-phosphate esters bearing various substituents, such as those for spin labeling and fluorescent labeling, on their phosphate groups. In addition, the stability of the inosine 6-phosphate esters toward cellular nucleases was examined to find that they were unstable and rapidly hydrolyzed in the presence of these enzymes. To solve this problem, we developed a method for the synthesis of inosine 6-thiophosphate esters, which were more stable toward these enzymes. The molecules developed in this study will be useful as molecular probes and therapeutic agents targeting the biosynthesis of nucleic acids.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (34 results)

All 2017 2016 2015 2014 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 4 results) Presentation (26 results) (of which Int'l Joint Research: 5 results,  Invited: 2 results) Remarks (3 results)

  • [Journal Article] Synthesis of 2-pyridylthiophosphinic acids and 2-pyridylthiophosphonate monoesters via nucleophilic aromatic substitution2017

    • Author(s)
      Natsuhisa Oka, Kensuke, Ori, Kaori Ando
    • Journal Title

      Phosphorus, Sulfur, and Silicon and the Related Elements

      Volume: 192 Issue: 4 Pages: 454-463

    • DOI

      10.1080/10426507.2016.1248763

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled solid-phase synthesis of PO/PS chimeric oligodeoxyribonucleotides on an automated synthesizer using an oxazaphospholidine-phosphoramidite method2016

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

      J. Org. Chem.

      Volume: 81 Issue: 7 Pages: 2753-2762

    • DOI

      10.1021/acs.joc.5b02793

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereocontrolled Synthesis of Phosphate-modified Oligonucleotides2016

    • Author(s)
      岡 夏央・和田 猛
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 1 Pages: 31-44

    • DOI

      10.5059/yukigoseikyokaishi.74.31

    • NAID

      130005126249

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enhancement of affinity of 2'-O-Me-oligonucleotides for complementary RNA by incorporating a stereoregulated boranophosphate backbone2015

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

      RSC Adv.

      Volume: 5 Issue: 4 Pages: 2392-2395

    • DOI

      10.1039/c4ra11335g

    • Related Report
      2015 Research-status Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] -Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide2014

    • Author(s)
      Oka, N.; Kajino, R.; Takeuchi, K.; Nagakawa, H.; Ando, K.
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 16 Pages: 7656-7664

    • DOI

      10.1021/jo500632h

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Fluorescent labeling of tRNA using tRNA guanine transglycosylase2016

    • Author(s)
      岡 夏央
    • Organizer
      2016分子化学研究会
    • Place of Presentation
      鳥取大学
    • Year and Date
      2016-11-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] 7-デアザグアニン誘導体の合成法の開発と応用2016

    • Author(s)
      福田 茜・岡 夏央・清水 陽介・安藤 香織・能村 友一朗・中村 浩史・大野 敏・横川 隆志
    • Organizer
      第47回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学
    • Year and Date
      2016-11-05
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of inosine 6-phosphate derivatives via phosphitylation of carbonyl oxygen2016

    • Author(s)
      Natsuhisa Oka, Tuta Itakura, Yasuhiro Morita, Kaori Ando
    • Organizer
      The 43rd International Symposium on Nucleic Acid Chemistry
    • Place of Presentation
      Kumamoto University
    • Year and Date
      2016-09-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] α-リボフラノシドの高立体選択的合成2016

    • Author(s)
      岡 夏央
    • Organizer
      第35回日本糖質学会年会
    • Place of Presentation
      高知市文化プラザ かるぽーと
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] キラルブレンステッド酸を用いる不斉ホスホロアミダイト法の開発2016

    • Author(s)
      岡 夏央
    • Organizer
      新学術領域「有機分子触媒」第6回公開シンポジウム
    • Place of Presentation
      大阪科学技術センター
    • Year and Date
      2016-01-22
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Asymmetric synthesis of phosphite triesters using chiral Brensted acid catalysts2015

    • Author(s)
      Natsuhisa Oka, Takahiro Oshima, Kensuke Ori, Tomoki Sakai, Naoki Seo, Kaori Ando
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] α-Selective ribofuranosylation using ribofuranosyl iodides as glycosyl donors2015

    • Author(s)
      Natsuhisa Oka, Rin Kajino, Kaori Ando
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] キラルブレンステッド酸を用いる亜リン酸トリエステルの不斉合成法の開発2015

    • Author(s)
      馬場直紀・岡夏央・大島嵩弘・安藤香織
    • Organizer
      第42回有機典型元素化学討論会
    • Place of Presentation
      名古屋大学野依記念学術交流館
    • Year and Date
      2015-12-03
    • Related Report
      2015 Research-status Report
  • [Presentation] O6-ホスホリルイノシン誘導体の合成法の開発2015

    • Author(s)
      板倉 佑太・岡 夏央・森田 康裕・安藤 香織
    • Organizer
      第46回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      三重大学工学部
    • Year and Date
      2015-11-07
    • Related Report
      2015 Research-status Report
  • [Presentation] キラル酸活性化剤を用いるジヌクレオシドホスホロチオエートの立体選択的合成2015

    • Author(s)
      瀬尾直幹・岡 夏央・小里 建喬・酒井 智紀・安藤 香織
    • Organizer
      第46回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      三重大学工学部
    • Year and Date
      2015-11-07
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of 7-ethynyl-7-deazaguanine and its incorporation into tRNA2015

    • Author(s)
      Natsuhisa Oka, Akane Fukuta, Yousuke Shimizu, Kaori Ando, Yuichiro Nomura, Satoshi Ohno, Takashi Yokogawa
    • Organizer
      The 42th International Symposium on Nucleic Acid Chemistry
    • Place of Presentation
      I-messae hall, Himeji
    • Year and Date
      2015-09-23
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] α-リボフラノシドの高立体選択的合成法の開発2015

    • Author(s)
      岡 夏央・梶野 麟・安藤 香織
    • Organizer
      第33回日本糖質学会年会
    • Place of Presentation
      東京大学安田講堂
    • Year and Date
      2015-07-31
    • Related Report
      2015 Research-status Report
  • [Presentation] Asymmetric synthesis of phosphite triesters using chiral Brensted acids2015

    • Author(s)
      Natsuhisa Oka, Kensuke Ori, Takahiro Ohshima, Tomoki Sakai, Kaori Ando
    • Organizer
      The 39th Naito Conference
    • Place of Presentation
      シャトレーゼ ガトーキングダム 札幌
    • Year and Date
      2015-07-06
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] キラルブレンステッド酸を用いる亜リン酸トリエステルの不斉合成法の開発2015

    • Author(s)
      大島 嵩弘・岡 夏央・安藤 香織
    • Organizer
      日本化学会第95春季大会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] キラル酸活性化剤を用いるジヌクレオシドホスホロチオエートの立体選択的合成2015

    • Author(s)
      小里 建喬・岡 夏央・安藤 香織
    • Organizer
      日本化学会第95春季大会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] α-リボフラノシドの高立体選択的合成法の開発2015

    • Author(s)
      梶野 麟・岡 夏央・安藤 香織
    • Organizer
      日本化学会第95春季大会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] キラルブレンステッド酸を用いる亜リン酸トリエステルの不斉合成法の開発2014

    • Author(s)
      大島 嵩弘・岡 夏央・安藤 香織
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学春日井キャンパス
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] キラル酸活性化剤を用いるジヌクレオシドホスホロチオエートの立体選択的合成法の開発2014

    • Author(s)
      小里 建喬・岡 夏央・酒井 智紀・安藤 香織
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学春日井キャンパス
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] α-リボフラノシドの高立体選択的合成法の開発2014

    • Author(s)
      梶野 麟・岡 夏央・安藤 香織
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学春日井キャンパス
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] カルボニル基がリン酸化されたイノシン誘導体の合成法の開発2014

    • Author(s)
      板倉 佑太・岡 夏央・森田 康裕・安藤 香織
    • Organizer
      第45回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      中部大学春日井キャンパス
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] Asymmetric synthesis of phosphite triesters using chiral Brønsted acids2014

    • Author(s)
      Natsuhisa Oka・Kensuke Ori・Takahiro Ohshima・Tomoki Sakai・Kaori Ando
    • Organizer
      新学術領域「有機分子触媒」第2回国際会議(兼)第7回有機触媒シンポジウム
    • Place of Presentation
      東京大学・伊藤国際学術研究センター「伊藤謝恩ホール」
    • Year and Date
      2014-11-21 – 2014-11-22
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of 7-ethynyl-7-deazaguanine and its application2014

    • Author(s)
      Natsuhisa Oka, Yousuke Shimizu, Akane Fukuta, Kaori Ando, Yuichiro Nomura, Satoshi Ohno, Takashi Yokogawa
    • Organizer
      The 41th International Symposium on Nucleic Acid Chemistry (ISNAC2014)
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2014-11-05 – 2014-11-07
    • Related Report
      2014 Research-status Report
  • [Presentation] カルボニル基のリン酸化反応を用いる核酸の生合成中間体アナログの合成2014

    • Author(s)
      岡 夏央・板倉 佑太・森田 康裕・安藤 香織
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Research-status Report
  • [Presentation] ヨウ化糖を用いるα-リボフラノシドの合成2014

    • Author(s)
      岡 夏央・梶野 麟・竹内 薫・永川 晴奈・安藤 香織
    • Organizer
      第33回日本糖質学会年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-08-10 – 2014-08-11
    • Related Report
      2014 Research-status Report
  • [Presentation] Stereocontrolled synthesis of P-chiral oligonucleotide analogs2014

    • Author(s)
      Natsuhisa Oka
    • Organizer
      1st Joint International Seminar of Faculty of Science and Technology (Universiti Kebangsaan Malaysia) and Faculty of Engineering (Gifu University) 2014
    • Place of Presentation
      University Hall, Gifu University
    • Year and Date
      2014-07-31 – 2014-08-01
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] ビナフチルリン酸塩を用いる不斉ホスホロアミダイト法の開発2014

    • Author(s)
      岡 夏央・酒井 智紀・小里 建喬・大島 嵩弘・安藤 香織
    • Organizer
      新学術領域「有機分子触媒」第4回公開シンポジウム(分子活性化-有機分子触媒合同シンポジウム)
    • Place of Presentation
      北海道大学学術交流会館
    • Year and Date
      2014-06-20 – 2014-06-21
    • Related Report
      2014 Research-status Report
  • [Remarks] 岐阜大学 工学部 化学・生命工学科 安藤研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~ando_ap/

    • Related Report
      2016 Annual Research Report
  • [Remarks] 岐阜大学 工学部 化学・生命工学科 安藤研究室 公式ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~ando_ap/index.html

    • Related Report
      2015 Research-status Report
  • [Remarks] 岐阜大学工学部化学・生命工学科安藤研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~ando.ap/

    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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