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Development of Dehydrative S-Allylation toward Synthetic Biology

Research Project

Project/Area Number 24655076
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

KITAMURA Masato  名古屋大学, 創薬科学研究科, 教授 (50169885)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsアリルアルコール / システイン / ペプチド修飾 / ルテニウム / アリル化 / 合成生物学 / S-アリル化
Research Abstract

S-Allylated cysteine and peptides show various biological activities. In order to efficient generate a series of chemical libraries, direct S-allylation of thiol-containing amino acid and peptides in the native form is favored. This ideal process has been firstly realized by use of our catalytic system consisting of either [CpRu(CH3CN)3]PF6 and 2-quinolinecarboxylic acid or the pai-allyl Ru complex. The S-allylation process even in aqueous media including an acetate buffer system with high reactivity and S-chemoselectivity, suggesting a possibility of application of the present method for cysteine-containing proteins. Various C(2)-substituted allyl alcohols can be utilized, paving a way to a new type of lipopeptide library

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (41 results)

All 2014 2013 2012 Other

All Journal Article (14 results) (of which Peer Reviewed: 6 results) Presentation (24 results) (of which Invited: 9 results) Book (3 results)

  • [Journal Article]2013

    • Author(s)
      Yamamura, T.; Nakatsuka, H.; Tanaka, S.; Kitamura, M.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Pages: 9318-9315

    • Related Report
      2013 Final Research Report
  • [Journal Article]2013

    • Author(s)
      Kitamura, M.; Miyata, K.; Seki, T.; Vatmurge, N.; Tanaka, S.
    • Journal Title

      Pure Appl. Chem.

      Volume: 85 Pages: 1121-1132

    • Related Report
      2013 Final Research Report
  • [Journal Article] Ferrocene, 1,1'-bis[(2R,4R)-2,4-diethyl-1-phosp hetanyl]-, stereoisomer; Ferrocene, 1,1'- bis[(2S,4S)-2,4-diethyl-1- phosphetanyl]-, stereoisomer, RN016222013

    • Author(s)
      北村雅人
    • Journal Title

      e-EROS

    • Related Report
      2013 Final Research Report
  • [Journal Article] Asymmetric Hydrogenation of tert-Alkyl Ketones: DMSO Effect in Unification of Stereoisomeric Ruthenium Complexes2013

    • Author(s)
      Tomoya Yamamura, Hiroshi Nakatsuka, Shinji Tanaka, Masato Kitamura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 35 Pages: 9313-9315

    • DOI

      10.1002/anie.201304408

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] CpRu-catalyzed asymmetric dehydrative allylation2013

    • Author(s)
      Masato Kitamura, Kengo Miyata, Tomoaki Seki, Namdev Vatmurge, Shinji Tanaka
    • Journal Title

      Pure and Applied Chemistry

      Volume: 85 Issue: 6 Pages: 1121-1132

    • DOI

      10.1351/pac-con-12-10-02

    • Related Report
      2013 Annual Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article]2012

    • Author(s)
      Xu, B-H.; Yanez, R. A. A.; Nakatsuka, H.; Kitamura, M.; Fröhlich, R.; Kehr, G.; Erker
    • Journal Title

      Chem. Asian J.

      Volume: 7 Pages: 1347-1356

    • Related Report
      2013 Final Research Report
  • [Journal Article]2012

    • Author(s)
      Nakatsuka, H.; Fröhlich, R.; Kitamura, M.; Kehr, G.; Erker, G.
    • Journal Title

      Eur. J. Inorg. Chem

      Pages: 1163-1166

    • Related Report
      2013 Final Research Report
  • [Journal Article]2012

    • Author(s)
      Miyata, K.; Kitamura, M.
    • Journal Title

      Synthesis

      Volume: 44 Pages: 2138-2146

    • Related Report
      2013 Final Research Report
  • [Journal Article]2012

    • Author(s)
      Seki, T.; Tanaka, S.; Kitamura, M.
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 608-611

    • Related Report
      2013 Final Research Report
  • [Journal Article] Reduction?Hydrogenation : C=C; Chemoselective2012

    • Author(s)
      塚本眞幸、北村雅人
    • Journal Title

      Comprehensive Chirality

    • Related Report
      2013 Final Research Report
  • [Journal Article] Reaction of Frustrated Lewis Pairs with Ketones and Esters2012

    • Author(s)
      Bao-Hua Xu, Raul Alfonso Adler Yanez, Hiroshi Nakatsuka, Masato Kitamura, Roland Frohlich, Gerald Kehr, Gerhard Erker
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 7 Issue: 6 Pages: 1347-1356

    • DOI

      10.1002/asia.201100960

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Double Arylation of Acetylenedicarboxylate with B(C_6F_5)_32012

    • Author(s)
      Hiroshi Nakatsuka, Roland Frohlich, Masato Kitamura, Gerald Kehr, Gerhard Erker
    • Journal Title

      European Journal of Inorganic Chemistry

      Volume: 8 Issue: 8 Pages: 1163-1166

    • DOI

      10.1002/ejic.201101413

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Dehydrative C-, N-, and O-Allylation Using Naph-diPIM-dioxoi-Pr-CpRu/p-TsOH Combined Catalyst2012

    • Author(s)
      K. Miyata, M. Kitamura
    • Journal Title

      Synthesis

      Volume: 44 Issue: 14 Pages: 608-611

    • DOI

      10.1055/s-0031-1290301

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Pyrrolidine-, Piperidine-, and Azepane-type N-Heterocycles with α-Alkenyl Substitution : the CpRu-Catalyzed Dehydrative Intramolecular N-Allylation Approach2012

    • Author(s)
      Tomoaki Seki, Shinji Tanaka, Masato Kitamura
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 2 Pages: 608-611

    • DOI

      10.1021/ol203218d

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 脱水型不斉Tsuji-Trost反応の開発2014

    • Author(s)
      北村雅人
    • Organizer
      集積化学成果報告会
    • Place of Presentation
      東京
    • Year and Date
      2014-01-25
    • Related Report
      2013 Final Research Report
  • [Presentation] 脱水型不斉Tsuji-Trost反応の開発2014

    • Author(s)
      北村雅人
    • Organizer
      集積化学公開シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-01-24
    • Related Report
      2013 Final Research Report
  • [Presentation] 脱水型不斉Tsuji-Trost反応の開発2014

    • Author(s)
      北村雅人
    • Organizer
      集積反応化学公開シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
  • [Presentation] 脱水型不斉Tsuji-Trost反応の開発2014

    • Author(s)
      北村雅人
    • Organizer
      集積反応化学平成25年度第2回成果報告会
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
  • [Presentation] 触媒的不斉水素化の開発・応用・機構解明2013

    • Author(s)
      北村雅人
    • Organizer
      平成25年有機合成化学後期(秋期)講習会
    • Place of Presentation
      東京
    • Related Report
      2013 Final Research Report
  • [Presentation] Development of Magnetically Separable Heterogeneous Deallylation Catalyst2013

    • Author(s)
      田中慎二、北村雅人
    • Organizer
      The 16th International Symposium Relation Between Homogeneous and Heterogeneous Catalysis
    • Place of Presentation
      札幌
    • Related Report
      2013 Final Research Report
  • [Presentation] 触媒的不斉水素化の開発・応用・機構解明2013

    • Author(s)
      北村雅人
    • Organizer
      平成25年度有機合成化学後期(秋期)講習会
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Development of Magnetically Separable Heterogeneous Deallylation Catalyst2013

    • Author(s)
      S. Tanaka, M. Kitamura
    • Organizer
      The 16th International Symposium on Relations Between Homogeneous ond Heterogeneous Catalysis
    • Place of Presentation
      Sapporo
    • Related Report
      2013 Annual Research Report
  • [Presentation] 脱水型不斉Tsuji-Trost反応2012

    • Author(s)
      北村雅人
    • Organizer
      第24回万有シンポジウム
    • Place of Presentation
      札幌
    • Year and Date
      2012-07-07
    • Related Report
      2013 Final Research Report
  • [Presentation] 2001年ノーベル賞-右手型と左手型の分子を作り分ける-2012

    • Author(s)
      北村雅人
    • Organizer
      あいちサイエンスフェスティバル
    • Place of Presentation
      豊橋
    • Year and Date
      2012-06-09
    • Related Report
      2013 Final Research Report
  • [Presentation] Design and Synthesis of Linear N4 Chiral Ligands : Its Application to Asymmetric Hydrogenation of Aromatic Ketones2012

    • Author(s)
      吉村正宏、北村雅人
    • Organizer
      Cambodian Malaysian Chemical Conference (CMCC) 2012
    • Place of Presentation
      カンボジア
    • Related Report
      2013 Final Research Report
  • [Presentation] CpRu-Catalyzed Dehydrative Allylation of Thiols and Application for Peptide Modification2012

    • Author(s)
      田中慎二、北村雅人
    • Organizer
      17th Malaysian Chemical Congress
    • Place of Presentation
      クアラルンプール
    • Related Report
      2013 Final Research Report
  • [Presentation] A New Method for Lipidation of Cysteine-containing Peptide2012

    • Author(s)
      田中慎二、Jaisankar, P.、北村雅人
    • Organizer
      第三回物質統合シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Final Research Report
  • [Presentation] CpRu-Catalyzed Asymmetric Dehydrative Allylation2012

    • Author(s)
      北村雅人
    • Organizer
      19th International Conference on Organic Synthesis and 24th Royal Australian Institute Organic Conference
    • Place of Presentation
      メルボルン
    • Related Report
      2013 Final Research Report
  • [Presentation] A New sp^2N Bidentate Ligand2012

    • Author(s)
      北村雅人
    • Organizer
      The 2nd International Conference on Molecular and Functional Catalysis
    • Place of Presentation
      シンガポール
    • Related Report
      2013 Final Research Report
  • [Presentation] New Chiral sp^2N Bidentate Ligand; Naph-diPIM-dioxo-R-Donor-Acceptor Bifunctional Catalyst-2012

    • Author(s)
      北村雅人
    • Organizer
      The 6th Takeda Science Foundation Symposium on PharmaSciences
    • Place of Presentation
      大阪
    • Related Report
      2013 Final Research Report
  • [Presentation] Design and Synthesis of Linear N4 Chiral Ligands: Its Application to Asymmetric Hydrogenation of Aromatic Ketones2012

    • Author(s)
      吉村正宏・北村雅人
    • Organizer
      Cambodian Malaysian Chemical Conference (CMCC) 2012
    • Place of Presentation
      Angkor Century Resort & Spa, Siem Reap, Cambodia
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] CpRu-Catalyzed Dehydrative Allylation of Thiols and Application for Peptide Modification.2012

    • Author(s)
      田中慎二・北村雅人
    • Organizer
      17th Malaysian Chemical Congress
    • Place of Presentation
      Kuala Lumpure, Malaysia
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] A New Method for Lipidation of Cysteine-containing Peptides2012

    • Author(s)
      田中慎二・Jaisankar,P.・北村雅人
    • Organizer
      第3回統合物質シンポジウム
    • Place of Presentation
      九州大学
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] CpRu–Catalyzed Asymmetric Dehydrative Allylation2012

    • Author(s)
      北村雅人
    • Organizer
      19th International Conference on Organic Synthesis and 24th Royal Australian Institute Organic Conference
    • Place of Presentation
      Melbourne
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] A New sp2N Bidentate Ligand2012

    • Author(s)
      北村雅人
    • Organizer
      The 2nd International Conference on Molecular and Functional Catalysis
    • Place of Presentation
      Singapore
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] New Chiral sp2N Bidentate Ligand: Naph-diPIM-dioxo-R ―Donor-Acceptor Bifunctional Catalyst―2012

    • Author(s)
      北村雅人
    • Organizer
      The 6th Takeda Science Foundation Symposium on PharmaSciences
    • Place of Presentation
      Osaka
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 2001年ノーベル賞 ―右手型と左手型の分子をつくり分ける―

    • Author(s)
      北村雅人
    • Organizer
      あいちサイエンスフェスティバル
    • Place of Presentation
      豊橋
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 脱水型不斉Tsuji–Trost反応

    • Author(s)
      北村雅人
    • Organizer
      第24回万有シンポジウム―有機合成化学の最前線―
    • Place of Presentation
      札幌
    • Related Report
      2012 Research-status Report
    • Invited
  • [Book] e-EROS2013

    • Author(s)
      Masato Kitamura
    • Total Pages
      1
    • Publisher
      Ferrocene, 1,1'-bis[(2R,4R)-2,4-diethyl-1-phosphetanyl]-, stereoisomer; Ferrocene, 1,1'-bis[(2S,4S)-2,4-diethyl-1-phosphetanyl]-, stereoisomer, RN01622
    • Related Report
      2012 Research-status Report
  • [Book] Comprehensive Chirality2012

    • Author(s)
      Masaki Tsukamoto, Masato Kitamura
    • Total Pages
      4
    • Publisher
      Reduction – Hydrogenation: C ═ C; Chemoselective.
    • Related Report
      2012 Research-status Report
  • [Book] Comprehensive Chirality2012

    • Author(s)
      Seiji Suga, Masato Kitamura
    • Total Pages
      5
    • Publisher
      Asymmetric 1,2-Addition of Organometallics to Carbonyl and Imine Groups.
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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