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Action mechanism study of PF1171 hexapeptides focused on their 3D structures

Research Project

Project/Area Number 26850068
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Bioorganic chemistry
Research InstitutionMie University (2015-2016)
Tohoku University (2014)

Principal Investigator

MASUDA Yuichi  三重大学, 生物資源学研究科, 准教授 (90617755)

Co-Investigator(Renkei-kenkyūsha) KAI Kenji  大阪府立大学, 大学院生命環境科学研究科, 講師 (40508404)
Research Collaborator TANAKA Ren  東北大学, 大学院薬学研究科, 大学院生
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords環状ペプチド / カイコ / アポリポタンパク質B / X線結晶構造解析 / 核磁気共鳴 / 三次元構造 / 構造活性相関 / 分子プローブ / 有機化学 / 立体配座 / NMR / 光親和性標識 / 構造-活性相関 / 固相合成 / コンホメーション
Outline of Final Research Achievements

We achieved organic synthesis of PF1171 hexapeptides, cyclic peptides with paralytic activity against silkworms and inhibitory activity against production of apolipoprotein B. X-ray crystallography and nuclear magnetic resonance revealed significance of intramolecular hydrogen bonds in maintaining 3D structure of PF1171 hexapeptides. 3D structure-activity relationship study suggested that the 3D structure observed in the crystal is closely related to bioactivity. Based on the structure-activity relationship, we designed and synthesized molecular probes of PF1171 hexapeptides which can search for their target biomolecules.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (34 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 7 results,  Open Access: 7 results,  Acknowledgement Compliant: 5 results) Presentation (20 results) (of which Int'l Joint Research: 3 results,  Invited: 1 results) Remarks (5 results)

  • [Int'l Joint Research] University of East Anglia(英国)

    • Related Report
      2015 Research-status Report
  • [Journal Article] Design, Synthesis, and Biological Evaluation of Beauveriolide Analogues Bearing Photoreactive Amino Acids2016

    • Author(s)
      Masuda Y, Aoyama K, Yoshida M, Kobayashi K, Ohshiro T, Tomoda H, Doi T.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 754-765

    • DOI

      10.1248/cpb.c16-00095

    • NAID

      130005160040

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of (2S,3R,4R)-3,4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase.2016

    • Author(s)
      Masuda, Y., Maruyama, C., Kawabata, K., Hamano, Y., Doi, T.
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 36 Pages: 5602-5611

    • DOI

      10.1016/j.tet.2016.07.050

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 化学工業2016

    • Author(s)
      増田裕一,土井隆行
    • Journal Title

      生物活性環状ペプチドPF1171類とapratoxin Cの全合成と三次元構造解析

      Volume: 67 Pages: 18-25

    • Related Report
      2016 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Potent oxazoline analogue of apratoxin C: synthesis, biological evaluation, and conformational analysis.2016

    • Author(s)
      Yoshida, M., Onda, Y., Masuda, Y., Doi, T.
    • Journal Title

      Biopolymers (Peptide Science)

      Volume: 未定 Issue: 4 Pages: 404-414

    • DOI

      10.1002/bip.22781

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Structure revision of similanamide to PF1171C by total synthesis.2015

    • Author(s)
      Masuda, Y., Tanaka, R., Ganesan, A., Doi, T.
    • Journal Title

      J. Nat. Prod.

      Volume: 78 Issue: 9 Pages: 2286-2291

    • DOI

      10.1021/acs.jnatprod.5b00643

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Foxo3a Inhibitors of Microbial Origin, JBIR-141 and JBIR-1422015

    • Author(s)
      Teppei Kawahara, Noritaka Kagaya, Yuichi Masuda, Takayuki Doi, Miho Izumikawa, Kumiko Ohta, Atsushi Hirao, Kazuo Shin-ya
    • Journal Title

      Organic letters

      Volume: 17 Issue: 21 Pages: 5476-5479

    • DOI

      10.1021/acs.orglett.5b02842

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total synthesis and biological evaluation of PF1171A, C, F, and G, cyclic hexapeptides with insecticidal activity2014

    • Author(s)
      Masuda, Y., Tanaka, R., Kai, K., Ganesan, A., Doi, T.
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 17 Pages: 7844-7853

    • DOI

      10.1021/jo500861k

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Total Synthesis and Conformational Analysis of Apratoxin C2014

    • Author(s)
      Y. Masuda, J. Suzuki, Y. Onda, Y. Fujino, M. Yoshida, T. Doi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Issue: 17 Pages: 8000-8009

    • DOI

      10.1021/jo501130b

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] (2S,3R,4R)-3,4-dihydroxyarginineの合成と一酸化窒素合成酵素の阻害活性2017

    • Author(s)
      増田 裕一,丸山 千登勢,川畑 球一,濱野 吉十,土井 隆行
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都女子大学(京都府京都市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] 環状ペプチドの三次元構造に着目した構造-活性相関研究2016

    • Author(s)
      増田 裕一
    • Organizer
      第51回 天然物化学談話会
    • Place of Presentation
      湯沢東映ホテル(新潟県南魚沼郡)
    • Year and Date
      2016-07-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] カイコ麻痺活性を示す環状ペプチドPF1171類の三次元構造-活性相関2016

    • Author(s)
      増田裕一,田中錬,土井隆行
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌コンベンションセンター,札幌
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] Total synthesis and 3D structural analysis of apratoxin C2015

    • Author(s)
      Yuichi Masuda, Jun Suzuki, Masahito Yoshida, Takayuki Doi
    • Organizer
      International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthetic study of Asperterrestide A, a cytotoxic cyclic tetrapeptide2015

    • Author(s)
      Yuichi Masuda, Zhang Linnan, Takayuki Doi
    • Organizer
      Pharmaceutical Science Symposium 2015 in Sendai
    • Place of Presentation
      Sakura Hall in Tohoku University, Sendai
    • Year and Date
      2015-11-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 分子プローブを指向したPF1171F類縁体の合成と生物活性評価2015

    • Author(s)
      増田裕一,田中錬,土井隆行
    • Organizer
      第54回 日本薬学会東北支部大会
    • Place of Presentation
      岩手医科大学矢巾キャンパス,岩手
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic study for asperterrestide A2015

    • Author(s)
      増田裕一,張 林楠,土井隆行
    • Organizer
      第54回 日本薬学会東北支部大会
    • Place of Presentation
      岩手医科大学矢巾キャンパス,岩手
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 立体化学の解明を目指した4-hydroxycapreomycidineの全合成研究2015

    • Author(s)
      増田裕一,森田大貴,土井隆行
    • Organizer
      第54回 日本薬学会東北支部大会
    • Place of Presentation
      岩手医科大学矢巾キャンパス,岩手
    • Year and Date
      2015-09-26
    • Related Report
      2015 Research-status Report
  • [Presentation] カイコ麻痺活性を示す環状ペプチドPF1171類の全合成と三次元構造-活性相関2015

    • Author(s)
      増田裕一,田中錬,土井隆行
    • Organizer
      第57回 天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール,横浜
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic Study of Asperterrestide A2015

    • Author(s)
      Yuichi Masuda, Linnan Zhang, Takayuki Doi
    • Organizer
      Tohoku University's Chemistry Summer School 2015
    • Place of Presentation
      Tohoku University, Sendai
    • Year and Date
      2015-08-27
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 生物活性環状ペプチドPF1171類の構造活性相関研究2015

    • Author(s)
      増田裕一,田中錬,土井隆行
    • Organizer
      日本ケミカルバイオロジー学会 第10回年会
    • Place of Presentation
      東北大学萩ホール,仙台
    • Year and Date
      2015-06-10
    • Related Report
      2015 Research-status Report
  • [Presentation] 昆虫麻痺活性を示す環状ペプチドPF1171類の全合成と三次元構造解析2015

    • Author(s)
      増田裕一,田中錬,甲斐健次,A. Ganesan, 土井隆行
    • Organizer
      日本農芸化学会2015年度大会
    • Place of Presentation
      岡山大学,岡山
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 4-OH capreomycidine の全合成2015

    • Author(s)
      森田大貴,増田裕一,土井隆行
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学,兵庫
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] Total synthesis and 3D structural analysis of PF1171A, C, F, and G2014

    • Author(s)
      Yuichi Masuda, Ren Tanaka, Kenji Kai, A. Ganesan, and Takayuki Doi
    • Organizer
      第51回ペプチド討論会
    • Place of Presentation
      徳島大学蔵本キャンパス 大塚講堂,徳島
    • Year and Date
      2014-10-22 – 2014-10-24
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis and biological evaluation of PF1171F analogues2014

    • Author(s)
      Yuichi Masuda, Ren Tanaka, Kenji Kai, A. Ganesan, and Takayuki Doi
    • Organizer
      第51回ペプチド討論会
    • Place of Presentation
      徳島大学蔵本キャンパス 大塚講堂,徳島
    • Year and Date
      2014-10-22 – 2014-10-24
    • Related Report
      2014 Research-status Report
  • [Presentation] Apratoxin C オキサゾリン誘導体の全合成2014

    • Author(s)
      恩田勇一,鈴木淳,吉田将人,増田裕一,土井隆行
    • Organizer
      第53回日本薬学会東北支部大会
    • Place of Presentation
      いわき明星大学キャンパス,福島
    • Year and Date
      2014-10-05
    • Related Report
      2014 Research-status Report
  • [Presentation] アントラニル酸含有環状ペプチドPF1171類の全合成と昆虫麻痺活性評価2014

    • Author(s)
      増田裕一,田中錬,甲斐建次,A. Ganesan,土井隆行
    • Organizer
      平成26年度化学系学協会東北大会
    • Place of Presentation
      山形大学米沢キャンパス,山形
    • Year and Date
      2014-09-20 – 2014-09-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 生物活性環状ペプチドの合成と三次元構造解析2014

    • Author(s)
      増田 裕一
    • Organizer
      第13回化学系若手研究者セミナー
    • Place of Presentation
      東北薬科大学70周年記念講堂,仙台
    • Year and Date
      2014-09-06
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Total Synthesis and Biological Evaluation of PF1171A, C, F, and G2014

    • Author(s)
      Yuichi Masuda, Ren Tanaka, Kenji Kai, A. Ganesan, and Takayuki Doi
    • Organizer
      Tohoku University's Chemistry Summer School 2014
    • Place of Presentation
      Tohoku University, Sendai,Miyagi
    • Year and Date
      2014-08-24 – 2014-08-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 固体NMRを用いた生体分子の分子間相互作用の解析2014

    • Author(s)
      増田 裕一
    • Organizer
      第49回天然物化学談話会 ショートトーク
    • Place of Presentation
      せとうち児島ホテル,倉敷,岡山
    • Year and Date
      2014-07-02 – 2014-07-04
    • Related Report
      2014 Research-status Report
  • [Remarks] 創薬化学研究室の紹介ページ

    • URL

      http://www.cc.mie-u.ac.jp/~masuda/

    • Related Report
      2016 Annual Research Report
  • [Remarks] 三重大学教員紹介

    • URL

      http://kyoin.mie-u.ac.jp/profile/3065.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] 東北大学薬学部,大学院薬学研究科 反応制御化学分野のホームページ Doi Laboratory

    • URL

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

    • Related Report
      2015 Research-status Report
  • [Remarks] 三重大学教員紹介

    • URL

      http://www.bio.mie-u.ac.jp/academics/faculty/YuichiMasuda.html

    • Related Report
      2015 Research-status Report
  • [Remarks] 東北大学薬学部 大学院薬学研究科 反応制御化学分野のホームページ

    • URL

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

    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2022-02-03  

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