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Development of the novel chemoselective capture method for sphingolipids

Research Project

Project/Area Number 23651211
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
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)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsスフィンゴシン / グルタルアルデヒド / 捕捉 / 2-アミノ-1, 3-ジオール / 官能基特異的 / 2-アミノ-1,3-ジオール / 化学特異的 / 2-アミノ-1 / 3-ジオール
Research Abstract

To create new methodology of chemoselective catch toward sphingosine, large scale organic synthesis of target molecule was performed. Four standard samples having four different stereochemistries were prepared from D- and L-serine. The glutaraldehyde group was selected as functional group to react chemoselectively toward an 2-amino-1,3-diol function. The phenyl glutaraldehyde derivative was synthesized and connected with surface of the resin. The immobilization efficiency was confirmed by IR. The OPA derivatization method for detection of sphingosines reveals clearly its efficiency of the catching. To detect small amount of sphingosine in serum, downsizing of this new methodology was successfully performed utilizing the previously synthesize standard samples.

Report

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

    (27 results)

All 2013 2012 2011 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (22 results) (of which Invited: 6 results)

  • [Journal Article] Structural Diversity of New C13-Polyketides Produced by Chaetomium mollipilium Cultivated in the Presence of a NAD+-Dependent Histone Deacetylase Inhibitor2012

    • Author(s)
      Asai T., Morita S. Shirata N., Taniguchi T., Monde K. Sakurai H., Ozeki T. Oshima Y.
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 5456-5459

    • Related Report
      2013 Final Research Report 2012 Research-status 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 Pages: 3695-3698

    • NAID

      10031009371

    • Related Report
      2013 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantioselective 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.
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 2679-2686

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective 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.
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 2679-2686

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Salvileucalin C, a novel rearranged neoclerodane diterpene from Salvia leucantha2011

    • Author(s)
      Aoyagi Y., Yamazaki A., Kato R., Tobe F., Fukaya H., Nishikawa T., Nakahashi A., Miura N., Monde K., Takeya K.
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Pages: 1851-1853

    • Related Report
      2013 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] Development of an efficient capture resin for sphingolipids by using chemoselective reaction and stereochemical analysis method2013

    • Author(s)
      Ananda Kumar C. S., Saori Okamoto, Atsufumi Nakahashi, Tohru Taniguchi, Kenji Monde
    • 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
      早稲田大学西早稲田キャンパス(東京都新宿区)
    • Year and Date
      2013-03-01
    • Related Report
      2013 Final 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
      早稲田大学西早稲田キャンパス(東京都新宿区)
    • Year and Date
      2013-03-01
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] Development of an efficient capture resin for sphingolipids by using a chemoselective reaction and its applications2013

    • Author(s)
      Ananda Kumar C.S., Siddabasave Gowda B., Keiko Yamane, Saori Okamoto, Atsufumi Nakahashi, Mostafa A.S. Hammam, Tohru Taniguchi and Kenji Monde
    • Organizer
      The 11th International Symposium for Future Drug Discovery and Medical Care
    • Place of Presentation
      北海道大学(札幌市)
    • Related Report
      2013 Final Research Report
  • [Presentation] 官能基選択的反応を用いたスフィンゴ脂質類の効率的捕捉樹脂の開発と立体化学解析への展開2013

    • Author(s)
      アナンダクマール C.S., 岡本沙織, 中橋徳文, 谷口透, 門出健次
    • Organizer
      第20回記念シンポジウム モレキュラー・キラリティー2013
    • Place of Presentation
      京都大学(京都府京都市)
    • Related Report
      2013 Final Research Report
  • [Presentation] Development of an efficient capture resin for sphingolipids by using a chemoselective reaction and a stereochemical analysis method2013

    • Author(s)
      Ananda Kumar C.S., Saori Okamoto, Atsufumi Nakahashi, Mostafa A.S. Hammam, Tohru Taniguchi and Kenji Monde
    • Organizer
      International Conference on Chiroptical Spectroscopy
    • Place of Presentation
      Student Life center, Vanderbilt University(USA)
    • Related Report
      2013 Final Research Report
  • [Presentation] Stereochemical Analysis of Drug-like Molecules Assisting the Investigation of Stereochemistry in Drug Discovery2013

    • Author(s)
      Mostafa A.S. Hammam, Mikako Kato, Saori Okamoto, Ananda Kumar C.S., Atsufumi Nakahashi, Tohru Taniguchi and Kenji Monde
    • Organizer
      International Conference on Chiroptical Spectroscopy
    • Place of Presentation
      Student Life center, Vanderbilt University(USA)
    • Related Report
      2013 Final Research Report
  • [Presentation] Stereochemical Analysis of Drug-like Molecules Assisting the Investigation of Stereochemistry in Drug Discovery2013

    • Author(s)
      Mostafa A. S. Hammam, Mikako Kato, Saori Okamoto, Ananda Kumar C. S., Atsufumi Nakahashi, Tohro Taniguchi and Kenji Monde
    • Organizer
      International Conference on Chiroptical Spectroscopy
    • Place of Presentation
      Student Life center, Vanderbilt University (USA)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Development of an efficient capture resin for sphingolipids by using a chemoselective reaction and a stereochemical analysis method2013

    • Author(s)
      Ananda Kumar C. S, Okamoto saori, Atsufumi Nakahashi, Mostafa A. S. Hammam, Tohru Taniguchi, and Kenji Monde
    • Organizer
      International Conference on Chiroptical Spectroscopy
    • Place of Presentation
      Student Life center, Vanderbilt University (USA)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 官能基選択的反応を用いたスフィンゴ脂質類の効率的捕捉樹脂の開発と立体化学解析への展開2013

    • Author(s)
      アナンダクマールC.S 、岡本沙織、中橋徳文、谷口透、門出健次
    • Organizer
      第20回記念 シンポジウム モレキュラー・キラリティー2013
    • Place of Presentation
      京都大学、京都
    • Related Report
      2013 Annual Research Report
  • [Presentation] Development of an efficient capture resin for sphingolipids by using a chemoselective reaction and its applications2013

    • Author(s)
      Ananda Kumar C. S., Siddabasave Gowda B., Keiko Yamaane, Okamoto saori, Atsufumi Nakahashi, Mostafa A. S. Hammam, Tohru Taniguchi, and Kenji Monde
    • Organizer
      The 11th International Symposium for Future Drug Discovery and Medical Care
    • Place of Presentation
      北海道大学、札幌
    • 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
      徳島文理大学薬学部(徳島県徳島市)
    • Year and Date
      2012-12-22
    • Related Report
      2013 Final Research Report
    • Invited
  • [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(宮城県仙台市)
    • Year and Date
      2012-11-29
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] SYNTHESIS AND METABOLIC ANALYSIS OF FLUOROUS SPHINGOLIPIDS2011

    • Author(s)
      S. Saito, M. Yoshida, A. Nakahashi, M.A.S.Hammam, T. Taniguchi, S. Mitsutake, Y. Igarashi, K. Monde
    • Organizer
      International Symposium on Fluorous Technologies 2011 (ISoFT'11)
    • Place of Presentation
      香港城市大学(香港)
    • Year and Date
      2011-12-01
    • Related Report
      2013 Final Research Report
  • [Presentation] Structural Analysis of Sphingolipids by Vibrational Circular Dichroism2011

    • Author(s)
      Kenji Monde, Atsufumi Nakahashi, Mostafa A.S. Hammam, Saori Okamoto, Shota Saito, Tohru Taniguchi
    • Organizer
      13th International Conference on Chiroptical Spectroscopy (CD2011)
    • Place of Presentation
      Said Business School(イギリス)
    • Year and Date
      2011-07-27
    • Related Report
      2013 Final Research Report
  • [Presentation] VIBRATIONAL CIRCULR DICHROSIM a powerful tool for the determination of the structure and absolute configuration of chiral natural products in solution state2011

    • Author(s)
      Kenji Monde
    • Organizer
      27th International Symposium on the Chemistry of Natural Products (ISCNP27), 7th International Conference on Biodiversity (ICOB7)
    • Place of Presentation
      Brisbane Convention Centre(オーストラリア)
    • Year and Date
      2011-07-14
    • Related Report
      2013 Final Research Report
  • [Presentation] VIBRATIONAL CIRCULR DICHROSIM a powerful tool for the determination of the structure and absolute configuration of chiral natural products in solution state.2011

    • Author(s)
      Kenji Monde
    • Organizer
      27th International Symposium on the Chemistry of Natural Products (ISCNP27), 7th International Conference on Biodiversity (ICOB7)
    • Place of Presentation
      Brisbane Convention Centre(オーストラリア)
    • Related Report
      2011 Research-status Report
  • [Presentation] Structural Analysis of Sphingolipids by Vibrational Circular Dichroism2011

    • Author(s)
      Kenji Monde, Atsufumi Nakahashi, Mostafa A. S. Hammam, Saori Okamoto, Shota Saito, Tohru Taniguchi
    • Organizer
      13th International Conference on Chiroptical Spectroscopy (CD2011)(招待講演)
    • Place of Presentation
      Said Business School(イギリス)
    • Related Report
      2011 Research-status Report
  • [Presentation] SYNTHESIS AND METABOLIC ANALYSIS OF FLUOROUS SPHINGOLIPIDS2011

    • Author(s)
      S. Saito, M. Yoshida, A. Nakahashi, M. A. S. Hammam, T. Taniguchi, S. Mitsutake, Y. Igarashi, K. Monde
    • Organizer
      International Symposium on Fluorous Technologies 2011 (ISoFT’11)
    • Place of Presentation
      香港城市大学(香港)
    • Related Report
      2011 Research-status 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

    • 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(宮城県仙台市)
    • Related Report
      2012 Research-status Report
    • Invited
  • [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

    • 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
      徳島文理大学薬学部(徳島県徳島市)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 赤外円二色性スペクトルによるキラル解析の新展開

    • 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
      早稲田大学西早稲田キャンパス(東京都新宿区)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Development of an efficient capture resin for sphingolipids by using chemoselective reaction and stereochemical analysis method

    • Author(s)
      Ananda Kumar C. S., Saori Okamoto, Atsufumi Nakahashi, Tohru Taniguchi, Kenji Monde
    • 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
      早稲田大学西早稲田キャンパス(東京都新宿区)
    • Related Report
      2012 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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