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Total synthesis of a natural HIV protease inhibitor and its partial structures

Research Project

Project/Area Number 21710216
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

FUWA Haruhiko  東北大学, 大学院・生命科学研究科, 准教授 (90359638)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
KeywordsHIVプロテアーゼ / 全合成 / ディデムナケタール / 構造決定 / 天然物 / 構造活性相関 / 鈴木-宮浦反応 / 野崎-檜山-岸反応 / スピロアセタール / 天然物有機化学 / ライブラリー
Research Abstract

HIV protease is an enzyme responsible for the proteolysis of the polyprotein expressed by the retrovirus to produce matured proteins necessary for proliferation and infection. Thus, the inhibition of HIV protease represents an important therapeutic strategy for HIV-infected patients. In the present study, we have investigated synthetic routes toward marine natural products didemnaketals and their partial structures. We have completed the stereoselective syntheses of the C1-C11 acyclic domain and C9-C28 spiroacetal domain of didemnaketal B.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (14 results)

All 2012 2011 2010 2009

All Journal Article (9 results) (of which Peer Reviewed: 8 results) Presentation (5 results)

  • [Journal Article] Convergent Assembly of the Spiroacetal Subunit of Didemnaketal B2010

    • Author(s)
      Haruhiko Fuwa, Sayaka Noji, and Makoto Sasaki
    • Journal Title

      Org. Lett.

      Volume: 12 Pages: 5354-5357

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Exiguolide2010

    • Author(s)
      不破春彦, 佐々木誠
    • Journal Title

      Organic Letters 12

      Pages: 584-587

    • NAID

      110009757755

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Efficient Synthesis of Medium-Sized Lactones via Oxidative Lact onization : Concise Total Synthesis of Isolaurepan2010

    • Author(s)
      M.Ebine, Y.Suga, H.Fuwa, M.Sasaki
    • Journal Title

      Organic & Biomolecular Chemistry 8

      Pages: 39-42

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis and Biological Evaluation of (+)-Neopeltolide and Its Analogues2009

    • Author(s)
      H.Fuwa, A.Saito, S.Naito, K.Konoki, M.Yotsu-Yamashita, M.Sasaki
    • Journal Title

      Chemistry-a European Journal 15

      Pages: 12807-12818

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Toward the Total Synthesis of Goniodomin A, an Actin-Targeting Marine Polyether Macrolide : Convergent Synthesis of the C15-C36 Segment2009

    • Author(s)
      T.Saito, H.Fuwa, M.Sasaki
    • Journal Title

      Organic Letters 11

      Pages: 5274-5277

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of the DEFG-Ring Skeleton of Gambieric Acids2009

    • Author(s)
      H.Fuwa, S.Noji, M.Sasaki
    • Journal Title

      Chemistry Letters 38

      Pages: 866-867

    • NAID

      10025125515

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies on Gambieric Acids, Potent Antifungal Polycychc Ether Natural Products : Reassignment of the Absolute Configuration of the Nonacychc Polyether Core by NMR Analysis of Model Compounds2009

    • Author(s)
      H.Fuwa, K.Ishigai, T.Goto, A.Suzuki, M.Sasaki
    • Journal Title

      The Journal of Organic Chemistry 74

      Pages: 4024-4040

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Proteomic Analysis Reveals Multiple Patterns of Response in Cells Exposed to a Toxin Mixture2009

    • Author(s)
      G.L.Sala, G.Ronzitti, M.Sasaki, H.Fuwa, T.Yasumoto, A.Bigiani, G.P.Rossini
    • Journal Title

      Chemical Research in Toxicology 22

      Pages: 1077-1085

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 抗腫瘍性海産マクロリド(+)-ネオペルトリドの全合成2009

    • Author(s)
      佐々木誠、不破春彦
    • Journal Title

      ファルマシア 45

      Pages: 439-444

    • Related Report
      2009 Annual Research Report
  • [Presentation] ディデムナケタールBの全合成研究2012

    • Author(s)
      関根久美子, 不破春彦, 佐々木誠
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-27
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] ディデムナケタールC1-C11フラグメントの立体選択的合成2011

    • Author(s)
      関根久美子, 不破春彦, 佐々木誠
    • Organizer
      平成23年度化学系学協会東北大会
    • Place of Presentation
      仙台
    • Year and Date
      2011-09-17
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Studies toward the total synthesis of didemnaketals2010

    • Author(s)
      Sayaka Noji, Haruhiko Fuwa, and Makoto Sasaki
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-18
    • Related Report
      2010 Final Research Report
  • [Presentation] 複雑な構造を有する海洋天然有機化合物の効率的全合成2010

    • Author(s)
      不破春彦
    • Organizer
      日本化学会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] ディデムナケタールBのC9-C28サブユニットの合成研究2010

    • Author(s)
      野地紗也加, 不破春彦, 佐々木誠
    • Organizer
      第90回日本化学会春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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