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Development of the novel determination methodology for absolute configuration without theoretical calculation

Research Project

Project/Area Number 24310151
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Living organism molecular science
Research InstitutionHokkaido University

Principal Investigator

MONDE Kenji  北海道大学, 先端生命科学研究科(研究院), 教授 (40210207)

Co-Investigator(Kenkyū-buntansha) TANIGUCHI Tohru  北海道大学, 先端生命科学研究院, 助教 (00587123)
MURAI Yuta  北海道大学, 先端生命科学研究院, 助教 (20707038)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥19,630,000 (Direct Cost: ¥15,100,000、Indirect Cost: ¥4,530,000)
Fiscal Year 2014: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2013: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2012: ¥8,320,000 (Direct Cost: ¥6,400,000、Indirect Cost: ¥1,920,000)
KeywordsVCD / 絶対配置 / 励起き子 / キラリティー / カルボニル / 励起子 / 非経験的 / コンフォメーション / 角度依存性
Outline of Final Research Achievements

Vibrational circular dichroism (VCD) is a reliable and non-empirical method which can determine absolute configuration. However, ab initio theoretical calculation for its conformational analysis of a target molecule is essential. In this project, a new methodology for determination of absolute configuration without its theoretical calculation has been developed by utilizing a huge bisignate VCD signal caused by their interaction of two IR functional groups such as carbonyl groups in a target molecule.
This novel methodology named as “VCD exciton chirality method” has been applied to a variety of carbohydrates, steroids, complex natural products, acyclic biological active lipids, and poly lactic acid as a polymer, which shows its high applicability.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (27 results)

All 2014 2013 2012

All Journal Article (13 results) (of which Peer Reviewed: 12 results) Presentation (13 results) (of which Invited: 3 results) Book (1 results)

  • [Journal Article] Revision of the relative and absolute stereochemistry of 3-hydroxydehydroiso-α-lapachone and its derivatives.2014

    • Author(s)
      Khandelwal, P., Singh, P., Taniguchi, T., Monde, K., Johmoto, K., Uekusa, H., Masubuti, H., Fujimoto, Y.
    • Journal Title

      Phytochemistry Lett.

      Volume: 10 Pages: 224-229

    • DOI

      10.1016/j.phytol.2014.10.004

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues2014

    • Author(s)
      Salayova A., Kudlicova Z., Balaz M., Budovska M., Pilaova M., Mojzis J., Monde K., Petrovaj J., Gondova T.
    • Journal Title

      Tetrahedron Asymmetry

      Volume: 25 Issue: 16-17 Pages: 1221-1233

    • DOI

      10.1016/j.tetasy.2014.07.006

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] In Depth Study on Solution-State Structure of Poly(lactic acid) by Vibrational Circular Dichroism2014

    • Author(s)
      Hongen, T., Taniguchi, T. Nomura, S., Kadokawa, J., Monde, K.
    • Journal Title

      Macromolecules

      Volume: 47 Issue: 15 Pages: 5313-5319

    • DOI

      10.1021/ma501020s

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective intramolecular aza-spiroannulation onto benzofurans using chiral rhodium catalysis2014

    • Author(s)
      Shibuta, T., Sato, S., Shibuya, M., Kanoh, N., Taniguchi, T., Monde, K., Iwabuchi, Y.
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 32 Pages: 631-639

    • DOI

      10.1002/chin.201432120

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Short Synthesis of Berkeleyamide D and Determination of the Absolute Configuration by the Vibrational Circular Dichroism Exciton Chirality Method.2014

    • Author(s)
      Kenta Komori, Tohru Taniguchi, Shoma Mizutani, Kenji Monde, Kouji Kuramochi, Kazunori Tsubaki
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 5 Pages: 1386-1389

    • DOI

      10.1021/ol500148g

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective intramolecular aza-spiroannulation onto benzofurans using chiral rhodium catalysis2014

    • Author(s)
      T. Shibuta, S. Sato, M. Shibuya, N. Kanoh, T. Taniguchi, K. Monde, Y. Iwabuchi
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 3 Pages: 631-639

    • DOI

      10.3987/com-14-12941

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structures of Spiroindicumides A and B, Unprecedented Carbon Skeletal Spirolactones, and Determination of the Absolute Configuration by Vibrational Circular Dichroism Exciton Approach.2013

    • Author(s)
      Teigo Asai, Tohru Taniguchi, Takashi Yamamoto, Kenji Monde, Yoshiteru Oshima
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 17 Pages: 4320-4323

    • DOI

      10.1021/ol401741z

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structurally Diverse Chaetophenol Productions Induced by Chemically Mediated Epigenetic Manipulation of Fungal Gene Expression2013

    • Author(s)
      T. Asai, T. Yamamoto, N. Shirata, T. Taniguchi, K. Monde, I. Fujii, K. Gomi, Y. Oshima
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 13 Pages: 3346-3349

    • DOI

      10.1021/ol401386w

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structures and absolute configurations of short-branched fatty acid dimers from an endophytic fungus of Aloe arborescens2013

    • Author(s)
      T. Asai, S. Otsuki, T. Taniguchi, K. Monde, K. Yamashita, H. Sakurai, T. Ozekid, Y. Oshima
    • Journal Title

      Tetrahedron Lett

      Volume: (In press) Issue: 26 Pages: 3402-3405

    • DOI

      10.1016/j.tetlet.2013.04.063

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] tioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition2012

    • Author(s)
      Shibata, T.; Miyoshi, M.; Uchiyama, T.; Endo, K.; Miura, N.; Monde, K.Enan
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 12 Pages: 2679-2686

    • DOI

      10.1016/j.tet.2012.01.046

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dihydrobenzofurans as Cannabinoid Receptor Ligands, from Cordyceps annullata, an Entomopathogenic Fungus, Cultivated in the Presence of HDAC Inhibitor2012

    • Author(s)
      Teigo Asai, Dan Luo, Yutaro Obara, Toru Taniguchi, Kenji Monde, Kouwa Yamashita and Yoshiteru Oshima
    • Journal Title

      Tetrahedron Lett

      Volume: 53 Issue: 17 Pages: 2239-2243

    • DOI

      10.1016/j.tetlet.2012.02.088

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Exciton Chirality Method in Vibrational Circular Dichroism2012

    • Author(s)
      Taniguchi T, Monde K
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 8 Pages: 134-134

    • DOI

      10.1021/ja3001584

    • NAID

      120005333599

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 赤外円二色性スペクトル法における新展開2012

    • Author(s)
      門出 健次
    • Journal Title

      高分子

      Volume: 60 Pages: 779-780

    • NAID

      10031009371

    • Related Report
      2012 Annual Research Report
  • [Presentation] Development of a efficient methodology for the rapid isolation of bioactive sphingoid bases toward chemical library2014

    • Author(s)
      Kenji Monde
    • Organizer
      Asian Chemical Biology Initiative
    • Place of Presentation
      Hangzhou  (China)
    • Year and Date
      2014-11-22 – 2014-11-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Solution-State Helical Structural Study of Poly-L-Lactic Acid by VCD2014

    • Author(s)
      Kenji Monde
    • Organizer
      Molecular Chirality Asia
    • Place of Presentation
      Beijing (China)
    • Year and Date
      2014-10-30 – 2014-10-31
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Chiral Analysis of Biologically Important Molecules by VCD with and without DFT Theoretical Calculations2014

    • Author(s)
      Kenji Monde
    • Organizer
      4th International Conference on Vibrational Optical Activity (VOA-4)
    • Place of Presentation
      Baoding, Hebei Province (China)
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Analysis and Applications of Chiral Biomolecules by Vibrational Circular Dichroism2014

    • Author(s)
      Kenji Monde
    • Organizer
      CRC International Symposium
    • Place of Presentation
      北海道大学 (札幌市、北海道)
    • Year and Date
      2014-09-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Vibrational CD spectroscopy as a powerful tool for chiral analysis of flavor compounds2014

    • Author(s)
      Kenji Monde
    • Organizer
      248th ACS National Meeting & Exposition
    • Place of Presentation
      San Francisco (USA)
    • Year and Date
      2014-08-10 – 2014-08-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] Helical Nature of Polyester Studied by VCD2014

    • Author(s)
      Kenji Monde
    • Organizer
      CHIRALITY 2014
    • Place of Presentation
      Prague (Czech Republic)
    • Year and Date
      2014-07-27 – 2014-07-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] 溶液中におけるポリ乳酸らせん構造のVCD解析2014

    • Author(s)
      門出 健次
    • Organizer
      Symposium on Molecular Chirality 2014
    • Place of Presentation
      仙台国際センター (宮城県仙台市)
    • Year and Date
      2014-06-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] Chirality in Chemical Biology Utilizing Vibrational Circular Dichroism2014

    • Author(s)
      Kenji Monde
    • Organizer
      Asian Chemical Biology Initiative 2014 Manila Meeting
    • Place of Presentation
      Manila Hotel (Philippines)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 赤外円二色性スペクトルによるキラル解析の新展開2013

    • Author(s)
      門出 健次
    • Organizer
      第4回キラルサイエンス&テクノロジーシンポジウム
    • Place of Presentation
      早稲田大学(東京都新宿区)(招待講演)
    • Year and Date
      2013-03-01
    • Related Report
      2012 Annual Research Report
  • [Presentation] VCD Exciton Chirality Method for Stereochemical Analysis2013

    • Author(s)
      Kenji Monde
    • Organizer
      Nakanishi 88th Birthday Symposium
    • Place of Presentation
      Columbia University (USA)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Exciton Chirality Method in VCD2013

    • Author(s)
      Tohru Taniguchi; Daisuke Manai; Takahiro Hongen; Kenji Monde
    • Organizer
      International Conference on Chiroptical Spectroscopy
    • Place of Presentation
      Student Life center, Vanderbilt University (USA)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 赤外円二色性スペクトルによる立体化学解析の新展開2012

    • Author(s)
      門出 健次
    • Organizer
      文部科学省戦略研究基盤形成事業「有機合成と天然物化学の手法による医薬品素材の開発」第9回研究発表会
    • Place of Presentation
      徳島文理大学(徳島市)(招待講演)
    • Year and Date
      2012-12-22
    • Related Report
      2012 Annual Research Report
  • [Presentation] 赤外円二色性スペクトルによるフッ素系キラル化合物の迅速立体構造解析2012

    • Author(s)
      門出 健次
    • Organizer
      フルオラス科学研究会第5回シンポジウム
    • Place of Presentation
      戦災復興記念館(宮城県)(招待講演)
    • Year and Date
      2012-11-29
    • Related Report
      2012 Annual Research Report
  • [Book] CSJカレントレビュー第13号『キラル化学―その起源から最新のキラル材料研究まで』2013

    • Author(s)
      門出健次
    • Publisher
      化学同人
    • Related Report
      2013 Annual Research Report

URL: 

Published: 2012-04-24   Modified: 2019-07-29  

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