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Toward the total synthesis of a hybrid natural product that consists a highly functionalized 11-oxatricycloundecane/macrolide and its structure activity relationships

Research Project

Project/Area Number 24790022
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKitasato University

Principal Investigator

SUGAWARA Akihiro  北里大学, その他の研究科, 助教 (50581683)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsルミナミシン / 抗嫌気性菌活性 / 全合成 / 11-オキサトリシクロウンデカン / 酸素架橋シスデカリン / マクロライド / 構造活性相関 / 高歪み10員環ラクトン / クロストリジウム属 / シスデカリン / 抗感染症薬
Research Abstract

Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria in 1985. It contains a highly functionalized 11-oxatricycloundecane, associated with a 10-membered lactone moiety which possesses a (E)-trisubstituted olefin and a 14-membered macrolactone, with an enol ether conjugated with a maleic anhydride functionality.
We have been focusing on its total synthesis due to its intriguing structure and interesting biological activity. We synthesized a framework of the key intermediate from the unsaturated aldehyde via intramolecular 1,6-oxa-Michael reaction and stereoselective protonation at C4 position. Study toward the total synthesis of 1 is in progress in our laboratory.

Report

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

    (20 results)

All 2014 2013 2012 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (9 results) Remarks (3 results)

  • [Journal Article] Crystal structures of HIV-1 gp120 envelope glycoprotein in complex with NBD analogues that target the CD4-binding site2014

    • Author(s)
      Young Do Kwon, Judith M. LaLonde, Yongping Yang, Mark A. Elban, Akihiro Sugawara, Joel R. Courter, David M. Jones, Amos B. Smith III, Asim K. Debnath, Peter D. Kwong
    • Journal Title

      PLoS One

      Volume: 9 Issue: 1 Pages: e85940-e85940

    • DOI

      10.1371/journal.pone.0085940

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Leucomycin A 3, a 16-membered macrolide antibiotic, inhibits influenza A virus infection and disease progression2014

    • Author(s)
      Ryuichi Sugamata, Akihiro Sugawara, Tomokazu Nagao, Koya Suzuki, Tomoyasu Hirose, Ki-ichi Yamamoto, Masamichi Oshima, Kazuo Kobayashi, Toshiaki Sunazuka, Kiyoko S Akagawa, Satoshi Omura, Toshinori Nakayama, Kazuo Suzuki
    • Journal Title

      J Antibiot

      Volume: 67 Issue: 3 Pages: 213

    • DOI

      10.1038/ja.2013.132

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Observation of the controlled assembly of preclick components in the in situ click chemistry generation of a chitinase inhibitor2013

    • Author(s)
      Hirose T, Maita N, Taniguchi H, Sharpless KB, Omura S, Sunazuka T
    • Journal Title

      Proc.Natl.Acad.Sci. USA.

      Volume: 110 Issue: 40 Pages: 15892-15897

    • DOI

      10.1073/pnas.1315049110

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric total synthesis of neoxaline2013

    • Author(s)
      Tetsuya Ideguchi, Takeshi Yamada, Tatsuya Shirahata, Tomoyasu Hirose, Akihiro Sugawara, Yoshinori Kobayashi, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      J Am Chem Soc

      Volume: 135 Issue: 34 Pages: 12568-12571

    • DOI

      10.1021/ja406657v

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Human acidic mammalian chitinase as a novel target for anti-asthma drug design using in silico screening2013

    • Author(s)
      Masaki Wakasugi, Hiroaki Gouda, Tomoyasu Hirose, Akihiro Sugawara, Tsuyoshi Yamamoto, Kazuro Shiomi, Toshiaki Sunazuka, Satoshi Omura, Shuichi Hirono
    • Journal Title

      Bioorg Med Chem

      Volume: 21 Issue: 11 Pages: 3214-3220

    • DOI

      10.1016/j.bmc.2013.03.047

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Borrelidin analogues with antimalarial activity: design, synthesis and biological evaluation against Plasmodium falciparum parasites2013

    • Author(s)
      Akihiro Sugawara, Toshiaki Tanaka, Tomoyasu Hirose, Aki Ishiyama, Masato Iwatsuki, Yoko Takahashi, Kazuhiko Otoguro, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Bioorg Med Chem Lett

      Volume: 23 Issue: 8 Pages: 2302-2305

    • DOI

      10.1016/j.bmcl.2013.02.075

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel 12-membered non-antibiotic macrolides, EM900 series with anti-inflammatory and/or immunomodulatory activity; synthesis, structure?activity relationships and in vivo study2012

    • Author(s)
      Akihiro Sugawara, Akito Sueki, Tomoyasu Hirose, Hideaki Shima, Kiyoko S Akagawa, Satoshi?mura and Toshiaki Sunazuka
    • Journal Title

      J. Antibiot.

      Volume: 65 Issue: 9 Pages: 487-490

    • DOI

      10.1038/ja.2012.51

    • NAID

      10031044227

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Toward the total synthesis of Luminamicin : construction of 14-membered lactone framework possessing versatile enol ether moiety2012

    • Author(s)
      Aoi Kimishima, Tomoyasu Hirose, Akihiro Sugawara, Takanori Matsumaru, Kaoru Nakamura, Ken Katsuyama, Masaki Toda, Hirokazu Takada, Rokuro Masuma, Satoshi?mura, Toshiaki Sunazuka
    • Journal Title

      Tetrahedron Lett.

      Volume: 53 Issue: 23 Pages: 2813-2816

    • DOI

      10.1016/j.tetlet.2012.03.098

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Toward the total synthesis of Luminamicin; construction of 14-membered macrolide with enol ether conjugated with a maleic anhydride2013

    • Author(s)
      Hirokazu Takada, Akihiro Sugawara, Tomoyasu Hirose, Aoi Kimishima, Takanori Matsumaru, Masaki Toda, Takeshi Yamada, Satoshi?mura and Toshiaki Sunazuka
    • Organizer
      ICCA-13
    • Place of Presentation
      山梨県(富士ビューホテル)
    • Related Report
      2013 Final Research Report
  • [Presentation] Toward the total synthesis of Luminamicin; construction of 11?oxatricyclo[5.3.1. ^1,70^3,8]undecane skeleton2013

    • Author(s)
      Aoi Kimishima, Akihiro Sugawara, Tomoyasu Hirose, Hirokazu Takada, Takanori Matsumaru, Satoshi?mura and Toshiaki Sunazuka
    • Organizer
      ICCA-13
    • Place of Presentation
      山梨県(富士ビューホテル)
    • Related Report
      2013 Final Research Report
  • [Presentation] Toward the total synthesis of Luminamicin, a specific anti-anaerobic bacteriacide2013

    • Author(s)
      Akihiro Sugawara, Aoi Kimishima, Hirokazu Takada, Tomoyasu Hirose, Takanori Matsumaru, Satoshi?mura, Toshiaki Sunazuka
    • Organizer
      Annual Meeting of the American Society of Pharmacognosy
    • Place of Presentation
      USA (St. Louis)
    • Related Report
      2013 Final Research Report
  • [Presentation] Toward The Total Synthesis Of Luminamicin, A Specific Anti-Anaerobic Bacteriacide2013

    • Author(s)
      Akihiro Sugawara, Aoi Kimishima, Hirokazu Takada, Tomoyasu Hirose, Takanori Matsumaru, Satoshi Omura, Toshiaki Sunazuka
    • Organizer
      Annual Meeting of the American Society of Pharmacognosy
    • Place of Presentation
      USA (St. Louis)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Toward the total synthesis of Luminamicin; construction of 14-membered macrolide with enol ether conjugated with a maleic anhydride2013

    • Author(s)
      Hirokazu Takada, Akihiro Sugawara, Tomoyasu Hirose, Aoi Kimishima, Takanori Matsumaru, Masaki Toda, Takeshi Yamada, Satoshi Omura and Toshiaki Sunazuka
    • Organizer
      ICCA-13
    • Place of Presentation
      Japan (Yamanashi)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Toward the total synthesis of Luminamicin; construction of 11–oxatricyclo[5.3.1. 1,703,8]undecane skeleton2013

    • Author(s)
      Aoi Kimishima, Akihiro Sugawara, Tomoyasu Hirose, Hirokazu Takada, Takanori Matsumaru, Satoshi Omura and Toshiaki Sunazuka
    • Organizer
      ICCA-13
    • Place of Presentation
      Japan (Yamanashi)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Luminamicinの全合成研究 (1);共役無水マレイン酸含有14員環マクロライドの合成法の確立2013

    • Author(s)
      高田拓和、菅原章公、廣瀬友靖、君嶋葵、松丸尊紀、戸田正輝、大村智、砂塚敏明
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Luminamicinの全合成研究(2);11-oxatricyclo[5.3.1.0]undecane骨格の構築2013

    • Author(s)
      君嶋葵、菅原章公、廣瀬友靖、高田拓和、松丸尊紀、戸田正輝、大村智、砂塚敏明
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] マクロライド骨格をテンプレートとした新規キチナーゼ阻害剤の創製2013

    • Author(s)
      菅原章公、真板宣夫、廣瀬友靖、木村紗穂莉、斉藤佳史、山本剛、渡邉剛志、塩見和朗、中野洋文、谷口寿章、大村智、砂塚敏明
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://seibutuyuuki.sakura.ne.jp/

    • Related Report
      2013 Final Research Report
  • [Remarks] 北里大学北里生命科学研究所、大学院感染制御科学府 生物有機化学研究室

    • URL

      http://seibutuyuuki.sakura.ne.jp

    • Related Report
      2013 Annual Research Report
  • [Remarks] 北里大学北里生命科学研究所 生物有機化学研究室のホームページ

    • URL

      http://seibutuyuuki.sakura.ne.jp

    • Related Report
      2012 Research-status Report

URL: 

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

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