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Synthesis of biologically acitive natural product cyclodepsipeptides and their analogues

Research Project

Project/Area Number 23310145
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionTohoku University

Principal Investigator

DOI TAKAYUKI  東北大学, 薬学研究科(研究院), 教授 (90212076)

Project Period (FY) 2011-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥20,020,000 (Direct Cost: ¥15,400,000、Indirect Cost: ¥4,620,000)
Fiscal Year 2013: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2012: ¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Fiscal Year 2011: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Keywords生物活性分子の合成 / 環状デプシペプチド / ペプチドミメティクス / 生物活性天然物 / 固相合成 / 非天然型アミノ酸 / マクロラクタム化 / 化合物ライブラリー / 立体配座解析
Research Abstract

Cyclodepsipeptide natural products include optically active hydroxy acids as well as various unnatural amino acids and exhibit a variety of biological activity depending on the peptide sequence, chirality, and selection of the hydroxy acids. We have demonstrated (1) design and synthesis of peptide mimetics of apratoxin A and total synthesis of apratoxin C, (2) synthesis of water soluble telomestatin analogues that is as potent as telomestatin in telomerase inhibitory activity, (3) combinatorial synthesis of destruxin E analogues and their SAR study, (4) design and synthesis of peptide mimetics of beauveriolide III and synthesis of photoaffinity probes of beauveriolide III.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (35 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (17 results) (of which Invited: 2 results) Book (3 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Scalable Solution-Phase Synthesis of the Biologically Active Cyclodepsipeptide Destruxin E, a Potent Negative Regulator of Osteoclast Morphology2014

    • Author(s)
      M. Yoshida, H. Sato, Y. Ishida, H. Nakagawa, T. Doi
    • Journal Title

      J. Org. Chem

      Volume: 79(1) Issue: 1 Pages: 296-306

    • DOI

      10.1021/jo402437z

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis and Characterization of Thielocin B1 as a Protein-Protein Interaction Inhibitor of PAC3 Homodimer2014

    • Author(s)
      T. Doi, M. Yoshida, K. Ohsawa, K. Shin-ya, M. Takagi, Y. Uekusa, T. Yamaguchi, K. Kato, T. Hirokawa, T. Natsume
    • Journal Title

      Chem. Sci

      Volume: 5 Issue: 5 Pages: 1860-1868

    • DOI

      10.1039/c3sc53237b

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Hepta-oxazole Macrocyclic Analogues of Telomestatin and Evaluation of Their Telomerase Inhibitory Activities2013

    • Author(s)
      K. Shibata, M. Yoshida, T. Takahashi, M. Takagi, K. Shin-ya, T. Doi
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 86(12) Issue: 12 Pages: 1453-1465

    • DOI

      10.1246/bcsj.20130198

    • NAID

      130004153172

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design and synthesis of 2-phenyl-1,4-dioxa-spiro [4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A2013

    • Author(s)
      S. Fuse, K. Inaba, M. Takagi, M. Tanaka, T. Hirokawa, K. Johmoto, H. Uekusa, K. Shin-ya, T. Takahashi, T. Doi
    • Journal Title

      Eur. J. Med. Chem

      Volume: 66 Pages: 180-184

    • DOI

      10.1016/j.ejmech.2013.05.030

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Direct and Mild Formylation Method for Substituted Benzenes Utilizing Dichloromethyl Methyl Ether - Silver Trifluoromethanesulfonate2013

    • Author(s)
      K. Ohsawa, M. Yoshida, T. Doi
    • Journal Title

      J. Org. Chem

      Volume: 78(7) Issue: 7 Pages: 3438-3444

    • DOI

      10.1021/jo400056k

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Comprehensive Predictions of Target Proteins Based on Protein-Chemical Interaction Using Virtual Screening and Experimental Verifications.2012

    • Author(s)
      Kobayashi H, et al Imoto M and Sakakibara Y.
    • Journal Title

      BMC Chemical Biology

      Volume: 12 Issue: 1 Pages: 2-2

    • DOI

      10.1186/1472-6769-12-2

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of a Near Infrared Fluorescence Labeling Reagent : Synthesis of Indole-Functionalized Indocyanine Green Derivatives2012

    • Author(s)
      T. Doi, K. Oikawa, J. Suzuki, M. Yoshida, N. Iki
    • Journal Title

      Synlett

      Volume: 2 Issue: 02 Pages: 306-310

    • DOI

      10.1055/s-0031-1290139

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conformationally Restricted Analog and Biotin-Labeled Probe Based on Beauveriolide III2012

    • Author(s)
      T. Doi. T. Muraoka, D. Ohshiro, D. Matsuda, M. Yoshida, T. Takahashi, S. Omura, H. Tomoda
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: 22(1) Issue: 1 Pages: 696-699

    • DOI

      10.1016/j.bmcl.2011.10.045

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tandem-type Pd(II)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence : a novel route to 4-aryl-2-quinolinones2012

    • Author(s)
      Kiyofumi Inamoto, Junpei Kawasaki, Kou Hiroya, Yoshinori Kondo, Takayuki Doi
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 36 Pages: 4332-4334

    • DOI

      10.1039/c2cc30600j

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Shin-ya, Isolation of New Hexapeptides -JBIR-39 and JBIR-40- from a Marine Sponge-Derived Streptomyces sp. Sp080513SC-242011

    • Author(s)
      I. Kozone, M. Izumikawa, K. Motohashi, A. Nagai, M. Yoshida, T. Doi, M. Takagi, K
    • Journal Title

      J. Marine Sci. Res. Development

      Volume: 1(1) Pages: 1000101-1000101

    • URL

      http://www.omicsonline.org/2155-9910/2155-9910-1-101.php

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Spiruchostatin B Aided by an Automated Synthesizer2011

    • Author(s)
      S.Fuse, K.Okada, Y.Iijima, A.Munakata, K.Machida, T.Takahashi, M.Takagi, K.Shin-ya, T.Doi
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 9 Issue: 10 Pages: 3825-3833

    • DOI

      10.1039/c0ob01169j

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Optically Active Lycopladine A by Utilizing Diastereoselective Protection of Carbonyl Group in a 1,3-Cyclohexanedione Derivative2011

    • Author(s)
      Kou Hiroya, Yoshihiro Suwa, Yusuke Ichihashi, Kiyofumi Inamoto, Takayuki Doi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 76 Issue: 11 Pages: 4522-4532

    • DOI

      10.1021/jo200418y

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] アプラトキシンCの活性コンホメーションに着目した構造活性相関研究2014

    • Author(s)
      増田裕一,鈴木淳,吉田将人,土井隆行
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 骨吸収抑制作用を示す19員環デプシペプチド デストラキシンEの液相全合成2014

    • Author(s)
      吉田将人,佐藤寛,石田恵崇,中川大,土井隆行
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Solid-phase Total Synthesis od Spiruchostatin A2013

    • Author(s)
      Takayuki Doi
    • Organizer
      International Symposium on Integrated Synthesis 8
    • Place of Presentation
      Nara
    • Related Report
      2013 Final Research Report
  • [Presentation] 骨吸収抑制作用を有するデストラキシンE の全合成と構造活性相関研究2013

    • Author(s)
      吉田将人, 石田恵崇, 佐藤寛, 竹内久征, 村瀬隼人, 中川大, 土井隆行
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Final Research Report
  • [Presentation] 天然物の全合成と機能解明に向けたアプローチ2013

    • Author(s)
      土井隆行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      神奈川
    • Related Report
      2013 Final Research Report
  • [Presentation] Total Synthesis and Conformational Analysis of Apratoxin C2013

    • Author(s)
      Y. Masuda, J. Suzuki, M. Yoshida, T. Doi
    • Organizer
      APIPS 2013: 4th Asia-Pacific International Peptide Symposium, 50th Japanese Peptide Symposium
    • Place of Presentation
      Hotel Hankyu Expo Park, Osaka
    • Related Report
      2013 Annual Research Report
  • [Presentation] 生物活性環状デプシペプチド天然物の全合成,誘導体合成,活性評価、機能構造解析2013

    • Author(s)
      土井隆行
    • Organizer
      第30回有機合成化学セミナー
    • Place of Presentation
      せとうち児島ホテル,岡山
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 骨吸収抑制作用を有するデストラキシンEの全合成と構造活性相関研究2013

    • Author(s)
      吉田将人,石田恵崇,佐藤寛,竹内久征,村瀬隼人,中川大,土井隆行
    • 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
    • Related Report
      2013 Annual Research Report
  • [Presentation] 天然物の全合成と機能解明に向けたアプローチ2013

    • Author(s)
      土井隆行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Piperidamycin類の全合成研究2012

    • Author(s)
      関岡直樹, 高木基樹, 新家一男, 土井隆行
    • Organizer
      日本薬学会132年会
    • Place of Presentation
      北海道
    • Year and Date
      2012-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] デストラキシンE およびその誘導体の全合成と生物活性評価2012

    • Author(s)
      吉田将人, 石田恵崇, 竹内久征, 中川大, 八代田陽子, 吉田稔, 高木基樹, 新家一男, 土井隆行
    • Organizer
      第49回ペプチド討論会プログラム
    • Place of Presentation
      鹿児島
    • Related Report
      2013 Final Research Report
  • [Presentation] デストラキシンEおよびその誘導体の全合成と生物活性評価2012

    • Author(s)
      吉田将人,石田恵崇,竹内久征,中川大,八代田陽子,吉田稔,高木基樹,新家一男,土井隆行
    • Organizer
      第49回ペプチド討論会
    • Place of Presentation
      鹿児島
    • Related Report
      2012 Annual Research Report
  • [Presentation] Total Synthesis of Cyclicdepsipeptide Destruxin E and its Derivatives as a Potent V-ATPase Inhibitor2011

    • Author(s)
      M.Yoshida, Y.Ishida, H.Takeuchi, Y.Yashiroda, M.Yoshida, H.Nakagawa, M.Takagi, K.Shinya, T.Doi
    • Organizer
      AIMECS11
    • Place of Presentation
      東京
    • Year and Date
      2011-11-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] 分子プローブを指向したDestruxin E類縁体の全合成研究および生物活性評価2011

    • Author(s)
      吉田将人, 石田恵崇, 竹内久征, 八代田陽子, 吉田稔, 中川大, 高木基樹, 新家一男, 土井隆行
    • Organizer
      第50回日本薬学会東北支部大会
    • Place of Presentation
      仙台
    • Year and Date
      2011-10-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] タンパク質間相互作用阻害活性を示すThielocin B1の全合成と相互作用解析2011

    • Author(s)
      吉田将人, 大澤宏祐, 高木基樹, 広川貴次, 植草義徳, 加藤晃一, 新家一男, 夏目徹, 土井隆行
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Year and Date
      2011-09-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] Total Synthesis of Cyclicdepsipeptide Destruxin E and its Derivatives as a Potent V-ATPase Inhibitor2011

    • Author(s)
      Masahito Yoshida, Yoshitaka Ishida, Hisayuki Takeuchi, Yoko Yashiroda, Minoru Yoshida, Hiroshi Nakagawa, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Related Report
      2013 Final Research Report
  • [Presentation] タンパク質間相互作用阻害活性を示すThielocin B1 の全合成と相互作用解析2011

    • Author(s)
      吉田将人, 大澤宏祐, 高木基樹, 広川貴次, 植草義徳, 加藤晃一 ,新家一男, 夏目徹, 土井隆行
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Related Report
      2013 Final Research Report
  • [Book] 「生物活性天然有機化合物環状デプシペプチド(-)-アプラトキシンA の全合成,固相合成,類縁体合成」,遺伝子医学MOOK21 最新ペプチド合成技術とその創薬研究への応用,木曽良明・向井秀仁編2012

    • Author(s)
      土井隆行
    • Publisher
      メディカルドゥ
    • Related Report
      2013 Final Research Report
  • [Book] 遺伝子医学MOOK21号最新ペプチド合成技術とその創薬研究への応用2012

    • Author(s)
      木曽良明, 土井隆行, 他
    • Publisher
      株式会社メディカルドゥ
    • Related Report
      2011 Annual Research Report
  • [Book] 天然物合成で活躍した反応実験のコツとポイント2011

    • Author(s)
      菅敏幸, 林雄二郎, 土井隆行, 他
    • Publisher
      株式会社化学同人
    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~hannou/

    • Related Report
      2013 Final Research Report
  • [Remarks]

    • Related Report
      2011 Annual Research Report
  • [Patent(Industrial Property Rights)] 環状デプシペプチドの新規使用方法2012

    • Inventor(s)
      中尾洋一、前島寛、土井隆行、山下潤、魚崎英毅、福島弘之
    • Industrial Property Rights Holder
      中尾洋一、前島寛、土井隆行、山下潤、魚崎英毅、福島弘之
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-09-03
    • Related Report
      2012 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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