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Development of catalytic and asymmetric amide-forming reactions in protic solvents and stereo-selective labeling of D-amino acids

Research Project

Project/Area Number 25460013
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

Kitamura Masanori  金沢大学, 薬学系, 准教授 (80453835)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsトリアジン / アミド化 / 不斉合成 / 脱水縮合反応
Outline of Final Research Achievements

There were only a few examples of kinetic resolution of racemic amines by chiral catalysts when optically active amides are prepared from carboxylic acids and amines. In contrast, a chiral catalyst developed in this study recognized stereogenic centers of carboxylic acids in a triazine-based dehydrocondensing reaction. It was elucidated that structures of chiral tertiary amines and chlorotriazines affected enantio-selectivity of the products. This is a first catalytic reaction system that would afford chiral amides from racemic carboxylic acids, and therefore, it would be useful for development of pharmaceutical drugs. In addition, by using knowledge obtained in this study, novel triazine-based benzylating reagents and effective elimination reactions of triazinylammonium salts were developed.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (24 results)

All 2016 2015 2014 2013 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 1 results) Presentation (14 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results) Book (1 results) Remarks (2 results)

  • [Journal Article] O-Benzylation of Carboxylic Acids Using 2,4,6-Tris(benzyloxy)-1,3,5-triazine (TriBOT) under Acidic or Thermal Conditions2015

    • Author(s)
      Kohei Yamada, Saki Yoshida, Hikaru Fujita, Masanori Kitamura, and Munetaka Kunishima
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 36 Issue: 36 Pages: 7997-8002

    • DOI

      10.1002/ejoc.201501172

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Specific Labeling of Streptavidin for Better Understanding of Ligand Modification in Modular Method for Affinity Labeling (MoAL)2014

    • Author(s)
      Munetaka Kunishima, Daiki Kato, Shuichi Nakanishi, Masanori Kitamura, Kohei Yamada, Keiji Terao, Tomoya Asano
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 62 Issue: 11 Pages: 1146-1150

    • DOI

      10.1248/cpb.c14-00468

    • NAID

      130004712907

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Pyrrolidinium Salts Using a Triazine-based Reagent under Mild Conditions2014

    • Author(s)
      Masanori Kitamura, Seina Yamamura, Hiroko Kobayashi, Mariko Yamamoto, Kayo Tada, Kazuhito Hioki, Kohei Yamada, Munetaka Kunishima
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 10 Pages: 1593-1595

    • DOI

      10.1246/cl.140503

    • NAID

      130004427196

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of a New Benzylating Reagent Spontaneously Releasing Benzyl Cation Equivalents at Room Temperature2014

    • Author(s)
      Kohei Yamada, Yuichi Tsukada, Yukiko Karuo, Masanori Kitamura, Munetaka Kunishima
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 38 Pages: 12274-12278

    • DOI

      10.1002/chem.201403158

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions2014

    • Author(s)
      M. Kitamura, F. Kawasaki, K. Ogawa, S. Nakanishi, H. Tanaka, K. Yamada, M. Kunishima
    • Journal Title

      J. Org. Chem

      Volume: 79 Issue: 8 Pages: 3709-3714

    • DOI

      10.1021/jo500376m

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Study of 1,3,5-Triazine-Based Catalytic Amide-Forming Reactions: Effect of Solvents and Basicity of Reactants2013

    • Author(s)
      Munetaka Kunishima, Masanori Kitamura, Hiroyuki Tanaka, Ichiro Nakakura, Takahiro Moriya, Kazuhito Hioki
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 61 Issue: 8 Pages: 882-886

    • DOI

      10.1248/cpb.c13-00368

    • NAID

      130003360818

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Practical Method for p-Methoxybenzylation of Hydroxy Groups Using 2,4,6-Tris (p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)2013

    • Author(s)
      Kohei Yamada, Hikaru Fujita, Masanori Kitamura, Munetaka Kuni shima
    • Journal Title

      Synthesis

      Volume: 45 Issue: 21 Pages: 2989-2997

    • DOI

      10.1055/s-0033-1339713

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] アミド基を置換基に有するトリアジニルアンモニウム型脱水縮合剤の開発2016

    • Author(s)
      加藤大輝、矢内秀、木村円、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] Effect of carbon substituents on the reactivity of triazine-based dehydrocondensing reagents2015

    • Author(s)
      Sayaka Komine, Masanori Kitamura, Munetaka Kunishima
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii Convention Center
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Intramolecular cyclization using a π-deficient 1,3,5-triazine2015

    • Author(s)
      Masanori Kitamura
    • Organizer
      International Symposium on Organic Synthesis at GDUT
    • Place of Presentation
      Guangdong University of Technology
    • Year and Date
      2015-11-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 電子的効果の軽微な置換基を有するトリアジン型縮合剤の反応性に関する研究2015

    • Author(s)
      小峰彩、北村正典、岡田有加里、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] アミノトリアジンを脱離基とするベンジル化剤の開発:置換基効果に基づく分解反応の制御2015

    • Author(s)
      軽尾友紀子、小峰彩、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] π電子欠乏性新規トリアジン型脱水縮合剤の開発2015

    • Author(s)
      木村円、矢内秀、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] トリアジニルアミンを脱離基とした分子内閉環反応によるピロリジニウム塩の合成2014

    • Author(s)
      山村聖奈,北村正典,小林比呂子,山本真理子,多田佳世,日置和人,山田耕平,国嶋崇隆
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台、東北大学 川内萩ホール
    • Year and Date
      2014-11-11
    • Related Report
      2014 Research-status Report
  • [Presentation] 電子欠乏性アミノトリアジンを脱離基としたベンジル化剤の開発2014

    • Author(s)
      軽尾友紀子, 塚田裕以智, 山田耕平, 北村正典, 国嶋崇隆
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      北海道、札幌市民ホール
    • Year and Date
      2014-09-11
    • Related Report
      2014 Research-status Report
  • [Presentation] ベンジルカチオン種の求電子付加に基づくアミド結合開裂反応の開発2014

    • Author(s)
      軽尾友紀子,山田耕平,北村正典,国嶋崇隆
    • Organizer
      創薬懇話会 2014 in 岐阜
    • Place of Presentation
      岐阜、岐阜長良川温泉 ホテルパーク
    • Year and Date
      2014-07-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 未知の薬物標的タンパク質の探索を志向した親和標識化法2014

    • Author(s)
      加藤大輝, 北村正典, 山田耕平, 浅野智哉, 国嶋崇隆
    • Organizer
      創薬懇話会 2014 in 岐阜
    • Place of Presentation
      岐阜、岐阜長良川温泉 ホテルパーク
    • Year and Date
      2014-07-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 酸触媒トリアジン型パラメトキシベンジル化剤 (TriBOT-PM) の開発

    • Author(s)
      藤田 光,山田 耕平,北村 正典,国嶋 崇隆
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      長良川国際会議場(岐阜県)
    • Related Report
      2013 Research-status Report
  • [Presentation] New Acid-Catalyzed Benzylating Reagents with the Smallest Unit of Benzyl Imidate

    • Author(s)
      Kohei Yamada, Hikaru Fujita, Masanori Kitamura, Munetaka Kunishima
    • Organizer
      2013 International Joint Symposium on Pharmacy
    • Place of Presentation
      Auditorium at College of Pharmacy Pusan National University(Busan, Korea)
    • Related Report
      2013 Research-status Report
  • [Presentation] ベンジルイミダートを経由するアミド結合切断反応の開発

    • Author(s)
      軽尾友紀子,山田耕平,北村正典,国嶋崇隆
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部 百年講堂(福岡県)
    • Related Report
      2013 Research-status Report
  • [Presentation] 脱水縮合反応を基盤とするタンパク質修飾法(MoAL法)におけるプローブ設計とその評価

    • Author(s)
      加藤大輝,山田耕平,北村正典,浅野智哉,国嶋崇隆
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学(熊本県)
    • Related Report
      2013 Research-status Report
  • [Book] e-EROS (Encyclopedia of Reagents for Organic Synthesis): 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride2013

    • Author(s)
      Masanori Kitamura, Munetaka Kunishima
    • Total Pages
      5
    • Publisher
      John Wiley & Sons, Ltd
    • Related Report
      2013 Research-status Report
  • [Remarks]

    • URL

      http://www.p.kanazawa-u.ac.jp/~bioorg/index.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] 国嶋研究室ホームページ

    • URL

      http://www.p.kanazawa-u.ac.jp/~bioorg/index.html

    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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