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Synthetic model study of reactive species involved in biological reactions for chemical elucidation of redox regulatory mechanism

Research Project

Project/Area Number 20350017
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

GOTO Kei  Tokyo Institute of Technology, 大学院・理工学研究科, 教授 (70262144)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥18,980,000 (Direct Cost: ¥14,600,000、Indirect Cost: ¥4,380,000)
Fiscal Year 2010: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2009: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2008: ¥10,920,000 (Direct Cost: ¥8,400,000、Indirect Cost: ¥2,520,000)
Keywords有機元素化学 / 有機元素科学 / 酵素モデル / 硫黄化合物 / レドックス制御 / ヨウ化スルフェニル / システイン誘導体 / 分子キャビティ / 立体保護 / ヒドックス制御 / N-ヒドロキシスルフェンアミド / デンドリマー / スルフィニルラジカル
Research Abstract

Cysteine residues located in clefts within the proteins are sterically restrained from forming inter- or intramolecular bridging bonds. The reactive intermediates generated by their reactions with reactive oxygen and nitrogen species play a crucial role in redox regulation. However, many of these intermediates are notoriously unstable in artificial systems, and model studies on these species have been difficult due to their instability. In this study, novel nano-sized molecular cavities with bowl-shaped frameworks were developed for modeling such sterically isolated environment and applied for the stabilization of highly reactive chemical species involved in redox regulations. Some of the mechanisms proposed for biological transformations were demonstrated experimentally by utilizing these model systems.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (49 results)

All 2011 2010 2009 2008 Other

All Journal Article (28 results) (of which Peer Reviewed: 24 results) Presentation (21 results)

  • [Journal Article] Formation of a Unique Fluorosilene-KF Complex Bearing Bulky Substituents2011

    • Author(s)
      Mieda, E., Sasamori, T., Sase, S., Goto K., Tokitoh, N.
    • Journal Title

      Chem.Lett. 40

      Pages: 196-197

    • NAID

      10027815007

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] 分子キャビティを活用した含ヨウ素高反応性中間体の安定化2011

    • Author(s)
      後藤敬
    • Journal Title

      SIS Letters 12

      Pages: 2-11

    • NAID

      40022792022

    • Related Report
      2010 Final Research Report
  • [Journal Article] Formation of a Unique Fluorosilene-KF Complex Bearing Bulky Substituents2011

    • Author(s)
      E.Mieda, T.Sasamori, S.Sase, K.Goto, N.Tokitoh
    • Journal Title

      Chem.Lett.

      Volume: 40 Pages: 196-197

    • NAID

      10027815007

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Biologically-relevant Reactive Sulfur Species by Utilizing a Primary Alkyl Steric Protection Group2011

    • Author(s)
      S.Sase, Y.Aoki, N.Abe, K.Goto
    • Journal Title

      Phosphorus, Sulfur Silicon Relat. Elem.

      Volume: (In press)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 分子キャビティを活用した含ヨウ素高反応性中間体の安定化2011

    • Author(s)
      後藤敬
    • Journal Title

      SIS Letters

      Volume: (In press)

    • NAID

      40022792022

    • Related Report
      2010 Annual Research Report
  • [Journal Article] Modeling of the 5′-Deiodination of Thyroxine by Iodothyronine Deiodinase : Chemical Corroboration of a Selenenyl Iodide Intermediate2010

    • Author(s)
      Goto K., Sonoda, D., Shimada, K., Sase, S., Kawashima, T.
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 545-547

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photo- and Thermal Isomerization of Shuttlecock- and Bowl-Equipped Phenylazopyridines2010

    • Author(s)
      Suwa, K., Otsuki, J., Goto K.
    • Journal Title

      J.Phys.Chem.A 114

      Pages: 884-890

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalyst-free Syntheses of [2]Rotaxanes Utilizing a Pentacoordinated Hydrosilane as an End-capping Agent2010

    • Author(s)
      Domoto, Y., Fukushima, A., Kasuga, Y., Sase, S., Goto K., Kawashima, T.
    • Journal Title

      Org.Lett. 12

      Pages: 2586-2589

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] 5,6,7,12-Tetrahydro-6-(1-methylethyl)-12-phenyldibenz[c,f][1,5]azasilocine2010

    • Author(s)
      Goto K., Fukushima, A., Kawashima, T.
    • Journal Title

      Acta Crystallogr.Sect.E 66

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Pentacoordinated Phenoxysilane and Carboxysilanes with Intramolecular Nitrogen-Silicon Coordination2010

    • Author(s)
      Domoto, Y., Saruhashi, K., Fukushima, A., Sase, S., Goto K., Kawashima, T.
    • Journal Title

      Phosphorus, Sulfur Silicon Relat.Elem. 185

      Pages: 1221-1229

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalyst-free Syntheses of [2]Rotaxanes Utilizing a Pentacoordinated Hydrosilane as an End-capping Agent2010

    • Author(s)
      Y.Domoto, A.Fukushima, Y.Kasuga, S.Sase, K.Goto, T.Kawashima
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 2586-2589

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Pentacoordinated Phenoxysilane and Carboxysilanes with Intramolecular Nitrogen-Silicon Coordination2010

    • Author(s)
      Y.Domoto, K.Saruhashi, A.Fukushima, S.Sase, K.Goto, T.Kawashima
    • Journal Title

      Phosphorus, Sulfur Silicon Relat. Elem.

      Volume: 185 Pages: 1221-1229

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 5, 6, 7, 12-Tetrahydro-6-(1-methylethyl)-12-phenyldibenz [c, f] [1, 5] azasilocine2010

    • Author(s)
      K.Goto, A.Fukushima, T.Kawashima
    • Journal Title

      Acta Crystallogr., Sect.E 66

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Modeling of the 5'-Deiodination of Thyroxine by Iodothyronine Deiodinase : Chemical Corroboration of a Selenenyl Iodide Intermediate2010

    • Author(s)
      K.Goto, D.Sonoda, K.Shimada, S.Sase, T.Kawashima
    • Journal Title

      Angew.Chem., Int.Ed. 49

      Pages: 545-547

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photo-and Thermal Isomerization of Shuttlecock-and Bowl-Equipped Phenylazopyridines2010

    • Author(s)
      K.Suwa, J.Otsuki, K.Goto
    • Journal Title

      J.Phys.Chem.A 114

      Pages: 884-890

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stable Sulfenyl Iodide Bearing a Primary Alkyl Steric Protection Group with a Cavity-shaped Framework2009

    • Author(s)
      Sase, S., Aoki, Y., Abe, N., Goto K.
    • Journal Title

      Chem.Lett. 38

      Pages: 1188-1189

    • NAID

      10027175953

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Structural Characterization of a Mixed Aggregate Containing a Lithium Thiolate and a Lithium Amide2009

    • Author(s)
      Goto K., Takahashi, Y., Kawashima, T.
    • Journal Title

      J.Sulfur Chem. 30

      Pages: 365-369

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Shuttlecock- and Bowl-Equipped Phenylazopyridines and Photomodulation of Their Coordination Ability to Zn-porphyrin2009

    • Author(s)
      Suwa, K., Otsuki, J., Goto K.
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 2106-2108

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] 新規な立体保護基の開発と生体反応活性種安定化への応用2009

    • Author(s)
      後藤敬
    • Journal Title

      ファインケミカル 38

      Pages: 27-36

    • Related Report
      2010 Final Research Report
  • [Journal Article] Synthesis and Structural Characterization of a Mixed Aggregate Containing a Lithium Thiolate and a Lithium Amide2009

    • Author(s)
      K.Goto, Y.Takahashi, T.Kawashima
    • Journal Title

      J.Sulfur Chem. 30

      Pages: 365-369

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stable Sulfenyl Iodide Bearing a Primary Alkyl Steric Protection Group with a Cavity-shaped Framework2009

    • Author(s)
      S.Sase, Y.Aoki, N.Abe, K.Goto
    • Journal Title

      Chem.Lett. 38

      Pages: 1188-1189

    • NAID

      10027175953

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Shuttlecock- and Bowl-Equipped Phenylazopyridines and Photomodulation of Their Coordination Ability to Zn-porphyrin2009

    • Author(s)
      K. Suwa, J. Otsuki, K. Goto
    • Journal Title

      Tetrahedron lett. 50

      Pages: 2106-2108

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Pentacoordinated Phenoxysilane and Carbox ysilanes with Intramolecular Nitrogen-Silicon Coordination2009

    • Author(s)
      Y. Domoto, K. Saruhashi, A. Fukushima, S. Sase, K. Goto, T. Kawashima
    • Journal Title

      Phosphorus, Sulfur Silicon Relat. Elem. (In press)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Structural Characterization of a Mixed Aggregate Containing a Lithium Thiolate and a Lithium Amide2009

    • Author(s)
      K. Goto, Y. Takahashi, T. Kawashima
    • Journal Title

      Tetrahedron lett. (In press)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 新規な立体保護基の開発と生体反応活性種安定化への応用2009

    • Author(s)
      後藤 敬
    • Journal Title

      ファインケミカル 38

      Pages: 27-36

    • Related Report
      2008 Annual Research Report
  • [Journal Article] Chemistry of Calixfurans2008

    • Author(s)
      後藤敬
    • Journal Title

      Top.Heterocycl.Chem. 17

      Pages: 97-121

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chemistry of Calixfurans2008

    • Author(s)
      K. Goto
    • Journal Title

      Top. Heterocycl. Chem. 17

      Pages: 97-121

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Biologically-relevant Reactive Sulfur Species by Utilizing a Primary Alkyl Steric Protection Group

    • Author(s)
      Sase, S., Aoki, Y., Abe, N., Goto K.
    • Journal Title

      Phosphorus, Sulfur Silicon Relat.Elem. 印刷中

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Presentation] Bowl型脂肪族および芳香族置換基を活用したS-ニトロソチオールの反応性の解明2011

    • Author(s)
      阿部憲明, 佐瀬祥平, 後藤敬
    • Organizer
      日本化学会第91回春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 分子キャビティを活用したp-チオベンゾキノンの合成研究2011

    • Author(s)
      中村正輝, 佐瀬祥平, 後藤敬
    • Organizer
      日本化学会第91回春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Bowl型立体保護基を活用したN-ヒドロキシスルフェンアミドの反応性の解明2011

    • Author(s)
      石原充裕, 吉川修平, 佐瀬祥平, 後藤敬
    • Organizer
      日本化学会第91回春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Modeling of Reactive Species Derived from Cysteine and Selenocysteine Residues2010

    • Author(s)
      後藤敬
    • Organizer
      TITech/UniGE Symposium 2010
    • Place of Presentation
      Geneva, Switzerland
    • Year and Date
      2010-11-26
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Bowl型分子キャビティを活用したS-ニトロソチオールの熱分解機構の解明2010

    • Author(s)
      阿部憲明, 佐瀬祥平, 後藤敬
    • Organizer
      第37回有機典型元素化学討論会
    • Place of Presentation
      室蘭
    • Year and Date
      2010-11-26
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Bowl型立体保護基を有するN-ヒドロキシスルフェンアミドと求核剤との反応2010

    • Author(s)
      石原充裕, 吉川修平, 佐瀬祥平, 後藤敬
    • Organizer
      第37回有機典型元素化学討論会
    • Place of Presentation
      室蘭
    • Year and Date
      2010-11-26
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Syntheses of Biologically-relevant Reactive Sulfur Species by Utilizing a Primary Alkyl Steric Protection Group2010

    • Author(s)
      後藤敬, 青木洋平, 阿部憲明, 佐瀬祥平
    • Organizer
      24th International Symposium on the Organic Chemistry of Sulfur
    • Place of Presentation
      Florence, Italy
    • Year and Date
      2010-07-29
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 活性化学種の反応制御を指向したナノサイズ分子キャビティの開発2010

    • Author(s)
      後藤敬
    • Organizer
      有機合成化学協会関東支部有機合成化学ミニシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2010-07-03
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] デンドリマー型分子キャビティを活用したシステインモデル化合物の合成2010

    • Author(s)
      三崎朋子, 佐瀬祥平, 後藤敬
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] キャビティ型分子骨格を活用したベンゾキノン硫黄類縁体の合成研究2010

    • Author(s)
      中村正輝, 佐瀬祥平, 後藤敬
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] キャビティ型分子骨格を有するシステイン誘導体の合成2009

    • Author(s)
      三崎朋子, 佐瀬祥平, 後藤敬
    • Organizer
      第36回有機典型元素化学討論会
    • Place of Presentation
      鳥取
    • Year and Date
      2009-12-11
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Model Study on the Reaction Mechanism of Iodothyronine Deiodinase by Utilizing a Bowl-shaped Molecular Cavity2009

    • Author(s)
      K.Goto, D.Sonoda, S.Sase, T.Kawashima
    • Organizer
      The 14th Japan-Korea Seminar on Organic Chemistry
    • Place of Presentation
      熱海
    • Year and Date
      2009-10-26
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Modeling of Reactive Sulfur Species Derived from Cysteine Residues Using a Primary Alkyl Steric Protection Group2009

    • Author(s)
      後藤敬, 青木洋平, 阿部憲明, 佐瀬祥平
    • Organizer
      The 9th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Oviedo, Spain
    • Year and Date
      2009-07-04
    • Related Report
      2010 Final Research Report
  • [Presentation] Modeling of Reactive Sulfur Species Derivedfrom Cysteine Residues Using a Primary Alkyl Steric Protection Group2009

    • Author(s)
      K.Goto, Y.Aoki, N.Abe, S.Sase
    • Organizer
      The 9th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Oviedo, Spain
    • Year and Date
      2009-07-04
    • Related Report
      2009 Annual Research Report
  • [Presentation] Bowl型分子キャビティを活用したS-ニトロソチオールおよび関連化合物の反応性の解明2009

    • Author(s)
      後藤敬, 青木洋平, 吉川修平, 三崎朋子, 阿部憲明, 佐瀬祥平
    • Organizer
      第5回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      宇都宮
    • Year and Date
      2009-05-30
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] 芳香族C-H活性化を利用したナノサイズ分子キャビティの合成2009

    • Author(s)
      三崎朋子, 佐瀬祥平, 後藤敬
    • Organizer
      日本化学会第89回春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-29
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] ナノサイズ分子キャビティを活用した生体反応活性種のモデル研究2009

    • Author(s)
      後藤敬
    • Organizer
      山口大学大学院医学系研究科産学連携セミナー
    • Place of Presentation
      山口
    • Year and Date
      2009-01-29
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] Bowl型置換基を有するスルフェンアミド誘導体の合成と反応2008

    • Author(s)
      吉川修平, 佐瀬祥平, 後藤敬
    • Organizer
      第35回有機典型元化学討論会
    • Place of Presentation
      八王子
    • Year and Date
      2008-12-11
    • Related Report
      2010 Final Research Report
  • [Presentation] Bowl型置換基を有するスルフェンアミド誘導体の合成と反応2008

    • Author(s)
      吉川修平, 佐瀬祥平, 後藤 敬
    • Organizer
      第35回有機典型元素化学討論会
    • Place of Presentation
      八王子
    • Year and Date
      2008-12-11
    • Related Report
      2008 Annual Research Report
  • [Presentation] 新規なキャビティ型骨格を有するチオニトラートの構造と反応性2008

    • Author(s)
      後藤敬, 吉川修平, 青木洋平, 佐瀬祥平
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-10-05
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] Model Study on the Reaction Mechanism for a Thyroid Hormone-Activating Enzyme by Utilizing a Bowl-shaped Molecular Cavity2008

    • Author(s)
      K.Goto, D.Sonoda, T.Kawashima
    • Organizer
      19th IUPAC Conference on Physical Organic Chemistry
    • Place of Presentation
      Santiago de Compostela, Spain
    • Year and Date
      2008-07-14
    • Related Report
      2010 Final Research Report 2008 Annual Research Report

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

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