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Synthesis and Application of Unnatural Chiral Amino acids and Peptides

Research Project

Project/Area Number 23655086
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKyushu University

Principal Investigator

TOMOOKA Katsuhiko  九州大学, 先導物質化学研究所, 教授 (70207629)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords不斉合成・反応 / 非天然型キラリティー / アミノ酸 / ペプチド / 面不斉 / ケイ素不斉 / 不斉合成 / 立体化学挙動
Research Abstract

To develop the novel field of amino acid chemistry, we focused on the synthesis of chiral amino acids and peptides having dynamic chirality or a silicon stereocenter. We accomplished the synthesis of dynamic planar chiral amino acids and peptides having an orthocyclophane skeleton. Furthermore, we successfully developed a catalytic enantioselective approach to chiral alkenylhydrosilanes, which are potential chiral building blocks for chiral amino acids having a silicon stereocenter.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (29 results)

All 2013 2012 2011 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (24 results) (of which Invited: 3 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Catalytic Enantioselective Synthesis of Alkenylhydrosilanes2012

    • Author(s)
      Igawa, K.; Yoshihiro, D.; Ichikawa, N.; Kokan, N.; Tomooka, K.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 51 Pages: 12745-12748

    • DOI

      10.1002/anie.201207361

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Substitution Reaction at the Nitrogen of Arylsulfonamides with Phosphide Anion2012

    • Author(s)
      Yoshida Suguru, Igawa Kazunobu, Tomooka Katsuhiko
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 47 Pages: 19358-19361

    • DOI

      10.1021/ja309642r

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Igawa KazunobuPlanar-Chiral2012

    • Author(s)
      Tomooka Katsuhiko, Iso Chisato, Uehara Kazuhiro, Suzuki Masaki, Nishikawa-Shimono Rie
    • Journal Title

      Orthocyclophanes Angew. Chem. Int. Ed

      Volume: 51 Issue: 41 Pages: 10355-10358

    • DOI

      10.1002/anie.201204484

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Presentation] アルケニルヒドロシランの触媒的不斉合成とその変換2013

    • Author(s)
      井川和宣,吉廣大佑,市川延雅,友岡克彦
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      草津(立命館大学)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 面不斉・-アミノ酸とその誘導体の動的立体化学挙動2013

    • Author(s)
      井川和宣,野口恭平,川端健志,扇好信,友岡克彦
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      草津(立命館大学)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 16位に置換基を有する面不斉3-アザ[7]オルトシクロファンの合成とその立体化学2013

    • Author(s)
      畑山有介,井川和宣,友岡克彦
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      草津(立命館大学)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 6 位に置換基を有する面不斉 3-アザ[7]オルトシクロファンの合成とその動的立体化学挙動2013

    • Author(s)
      井川和宣,小川浩平,川端健志,上原和浩,友岡克彦
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      草津(立命館大学)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 面不斉[7]オルトシクロファンの合成とその立体化学2013

    • Author(s)
      井川和宣,町田康平,上原和浩,友岡克彦
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      草津(立命館大学)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 動的キラルなアルケンの設計,合成,応用2013

    • Author(s)
      友岡克彦
    • Organizer
      関学化学フォーラム(主催:関西学院大学理工学研究科)
    • Place of Presentation
      神戸(関西学院大学)
    • Year and Date
      2013-01-28
    • Related Report
      2012 Final Research Report
  • [Presentation] 非天然型キラル分子の化学2012

    • Author(s)
      友岡克彦
    • Organizer
      有機合成セミナー(主催:有機合成化学協会東海支部)
    • Place of Presentation
      名古屋(名古屋大学)
    • Year and Date
      2012-11-26
    • Related Report
      2012 Final Research Report
  • [Presentation] 動的面不斉を有するヘテロ中員環化合物の化学2012

    • Author(s)
      友岡克彦
    • Organizer
      第24 万有札幌シンポジウム
    • Place of Presentation
      札幌(北海道大学)
    • Year and Date
      2012-07-07
    • Related Report
      2012 Final Research Report
  • [Presentation] 面不斉ジペプチドの立体化学挙動2012

    • Author(s)
      井川和宣,野口恭平,友岡克彦
    • Organizer
      日本化学会第92 春季年会
    • Place of Presentation
      横浜(慶応義塾大学)
    • Year and Date
      2012-03-27
    • Related Report
      2012 Final Research Report
  • [Presentation] Chemistry of Planar Chiral Heterocycles2012

    • Author(s)
      Tomooka Katsuhiko
    • Organizer
      The 4th Novel Chiral Chemistries Japan
    • Place of Presentation
      東京(東京工業大学)
    • Year and Date
      2012-03-16
    • Related Report
      2012 Final Research Report
  • [Presentation] 面不斉ジペプチドの立体化学挙動2012

    • Author(s)
      井川和宣,野口恭平,友岡克彦
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Research-status Report
  • [Presentation] Asymmetric Synthesis of Sila-carboxylic Acid2011

    • Author(s)
      Igawa Kazunobu, Kokan Naoto, Tomooka Katsuhiko
    • Organizer
      The 10th International Symposium on Organic Reactions
    • Place of Presentation
      横浜(慶応義塾大学)
    • Year and Date
      2011-11-24
    • Related Report
      2012 Final Research Report
  • [Presentation] Enantioselective Synthesis of Si-stereogenic Silanol and Its Transformation2011

    • Author(s)
      Igawa Kazunobu, Takada Junko, Kokan Naoto, Tomohiro Shimono, Tomooka Katsuhiko
    • Organizer
      The 7th International Symposium on Integrated Synthesis
    • Place of Presentation
      神戸(シーサイドホテル舞子ビラ神戸)
    • Year and Date
      2011-10-10
    • Related Report
      2012 Final Research Report
  • [Presentation] Enantioselective Synthesis of Si-stereogenic Silanol and Its Transformation2011

    • Author(s)
      Kazunobu Igawa; Junko Takada; Naoto Kokan; Tomohiro Shimono; Katsuhiko Tomooka
    • Organizer
      The 7th International Symposium on Integrated Synthesis
    • Place of Presentation
      兵庫
    • Related Report
      2011 Research-status Report
  • [Presentation] Asymmetric Synthesis of Sila-carboxylic Acid2011

    • Author(s)
      Kazunobu Igawa; Naoto Kokan; Katsuhiko Tomooka
    • Organizer
      The 10th International Symposium on Organic Reactions(招待講演)
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Presentation] 動的面不斉を有するヘテロ中員環化合物の化学

    • Author(s)
      友岡克彦
    • Organizer
      第24万有札幌シンポジウム
    • Place of Presentation
      札幌(北海道大学)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 非天然型キラル分子の化学

    • Author(s)
      友岡克彦
    • Organizer
      有機合成セミナー(主催:有機合成化学協会東海支部)
    • Place of Presentation
      名古屋(名古屋大学)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 動的キラルなアルケンの設計,合成,応用

    • Author(s)
      友岡克彦
    • Organizer
      関学化学フォーラム(主催:関西学院大学理工学研究科)
    • Place of Presentation
      神戸(関西学院大学)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] アルケニルヒドロシランの触媒的不斉合成とその変換(1)

    • Author(s)
      井川和宣,吉廣大佑,市川延雅,友岡克彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2012 Annual Research Report
  • [Presentation] アルケニルヒドロシランの触媒的不斉合成とその変換(2)

    • Author(s)
      井川和宣,吉廣大佑,市川延雅,古閑直人,友岡克彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 面不斉γ-アミノ酸とその誘導体の動的立体化学挙動

    • Author(s)
      井川和宣,野口恭平,川端健志,扇好信,友岡克彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 1(6)位に置換基を有する面不斉3-アザ[7]オルトシクロファンの合成とその立体化学

    • Author(s)
      畑山有介,井川和宣,友岡克彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 6位に置換基を有する面不斉3-アザ[7]オルトシクロファンの合成とその動的立体化学挙動

    • Author(s)
      井川和宣,小川浩平,川端健志,上原和浩,友岡克彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 面不斉[7]オルトシクロファンの合成とその立体化学

    • Author(s)
      井川和宣,町田康平,上原和浩,友岡克彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.cm.kyushu-u.ac.jp/tomooka

    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] シロキサン類、シラノール、及びシラン類、並びにその製造方法2011

    • Inventor(s)
      友岡克彦,井川和宣,高田純子
    • Industrial Property Rights Holder
      友岡克彦
    • Acquisition Date
      2011-08-26
    • Related Report
      2012 Final Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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