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Chemical synthesis of unique AG-gangliosides and evaluations of nerve cell stimulation activities

Research Project

Project/Area Number 20710171
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Living organism molecular science
Research InstitutionThe Institute of Physical and Chemical Research

Principal Investigator

HANASHIMA Shinya  The Institute of Physical and Chemical Research, 糖鎖構造生物学研究チーム, 基幹研究所研究員 (50373353)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2009: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2008: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsガングリオシド / 合成 / シアル酸 / NMR / Siglec-2 / 糖脂質 / 糖鎖 / グリコシル化 / 有機合成 / 神経突起伸長
Research Abstract

Gangliosides isolated from starfish have unique glycan sequences and nerve cell stimulating activities. We focused on their unique glycan sequences and synthesized the glycan parts by developing novel sialylation strategies. Further, we analyzed the binding between a starfish glycan and a protein Siglec, expressing on mammalian cell surfaces and modulating their functions. We elucidated the binding epitope as the trisaccharide unit including the sialic acid residue. Our finding revealed the potential that inner sialic acid could be also recognized by Siglec, which would develop useful potential for inhibitors of Siglec.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (29 results)

All 2011 2010 2009 2008 Other

All Journal Article (15 results) (of which Peer Reviewed: 6 results) Presentation (14 results)

  • [Journal Article] Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques2011

    • Author(s)
      花島慎弥
    • Journal Title

      Bioorganic and Medicinal Chemistry

      Volume: 18 Pages: 3720-3725

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques2010

    • Author(s)
      Shinya Hanashima, Ken-ichi Sato, Yuko Naito, Hiromu Takematsu, Yasunori Kozutsumi, Yukishige Ito, Yoshiki Yamaguchi
    • Journal Title

      Bioorg. Med. Chem. 18

      Pages: 3720-3725

    • Related Report
      2010 Final Research Report
  • [Journal Article] Homogeneous glycoprotein synthesis using bacterial oligosaccharyltransferase2009

    • Author(s)
      Shinya Hanashima
    • Journal Title

      Trend in Glycosci. GlycoTech. 21

      Pages: 302-304

    • NAID

      10026977089

    • Related Report
      2010 Final Research Report
  • [Journal Article] Synthesis of the starfish ganglioside AG-2 pentasaccharide2009

    • Author(s)
      Shinya Hanashima, Yoshiki Yamaguchi, Yukishige Ito, Ken-ichi Sato
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 6150-6153

    • Related Report
      2010 Final Research Report
  • [Journal Article] Silylene/oxazolidinone double-locked sialic acid building blocks for the efficient sialylation reaction in dichloromethane2009

    • Author(s)
      Shinya Hanashima, Ken-ichi Sato, Yukishige Ito, Yoshiki Yamaguchi
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 4215-4220

    • Related Report
      2010 Final Research Report
  • [Journal Article] Sialylation Reactions Using N-Glycolylneuraminic Acid Phosphite Donor2009

    • Author(s)
      Shinya Hanashima, Taku Tomiya, Shoji Akai, Ken-ichi Sato
    • Journal Title

      Carbohydr. Res. 344

      Pages: 959-965

    • Related Report
      2010 Final Research Report
  • [Journal Article] Synthesis of the starfish ganglioside LLG-3 tetrasaccharide2009

    • Author(s)
      Shinya Hanashima, Daichi Ishikawa, Shoji Akai, Ken-ichi Sato
    • Journal Title

      Carbohydr. Res. 344

      Pages: 747-752

    • Related Report
      2010 Final Research Report
  • [Journal Article] Sialylation using N-glycolylneuraminyl phosphite donors to synthesize Neu5Gc-containing glycans2009

    • Author(s)
      Shinya Hanashima
    • Journal Title

      Carbohydrate Research 344

      Pages: 959-965

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silylene/Oxazolidinone Double-Locked Sialic Acid Building Blocks for Efficient Sialylation Reactions in Dichloromethane2009

    • Author(s)
      Shinya Hanashima
    • Journal Title

      European Journal of Organic Chemistry

      Pages: 4215-4220

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the starfish ganglioside AG2 pentasaccharide2009

    • Author(s)
      Shinya Hanashima
    • Journal Title

      Tetrahedron Letters 50

      Pages: 6150-6153

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Homogeneous glycoprotein synthesis using bacterial oligosaccharyltransferase2009

    • Author(s)
      Shinya Hanashima
    • Journal Title

      Trends in Glycoscience and Glycotechnology 21

      Pages: 302-304

    • NAID

      10026977089

    • Related Report
      2009 Annual Research Report
  • [Journal Article] Synthesis of the starfish ganglioside LLG-3 tetrasaccharide2009

    • Author(s)
      花島慎弥
    • Journal Title

      Carbohydrate Research (in press)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thioester-assisted .-sialylation reaction2008

    • Author(s)
      Shinya Hanashima, Shoji Akai, Ken-ichi Sato
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 5111-5114

    • Related Report
      2010 Final Research Report
  • [Journal Article] Thioester-assisted α-sialylation reaction2008

    • Author(s)
      花島慎弥
    • Journal Title

      Tetrahedron Letters 49

      Pages: 5111-5114

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent strategies for stereoselective sialylation reaction and their applications

    • Author(s)
      Shinya Hanashima
    • Journal Title

      Trend in Glycosci. GlycoTech.

    • Related Report
      2010 Final Research Report
  • [Presentation] Binding Analysis of Human Siglec-2 and Synthetic AG2 Pentasaccharide Using NMR2010

    • Author(s)
      花島慎弥
    • Organizer
      Technique理研ケミカルバイオロジー国際シンポジウム
    • Place of Presentation
      理化学研究所
    • Year and Date
      2010-10-26
    • Related Report
      2010 Final Research Report
  • [Presentation] Binding Analysis of Human Siglec-2 and Synthetic AG2 Pentasaccharide Using NMR Technique2010

    • Author(s)
      花島慎弥
    • Organizer
      理研ケミカルバイオロジー国際シンポジウム
    • Place of Presentation
      埼玉県和光市
    • Year and Date
      2010-10-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] ガングリオシド糖鎖の化学合成とNMRを用いた相互作用解析2009

    • Author(s)
      花島慎弥
    • Organizer
      第6回 糖鎖科学コンソーシアムシンポジウム
    • Place of Presentation
      大阪、千里
    • Year and Date
      2009-12-08
    • Related Report
      2009 Annual Research Report
  • [Presentation]2009

    • Author(s)
      Shinya Hanashima
    • Organizer
      Synthesis of the unique starfish ganglioside AG2 pentasaccharide using silylene/oxazolidinone double-locked building blocks 20th Joint Glycobiology Meeting
    • Place of Presentation
      Cologne, Germany
    • Year and Date
      2009-11-10
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis of the unique starfish ganglioside AG2 pentasaccharide using silylene/oxazolidinone double-locked building blocks2009

    • Author(s)
      花島慎弥
    • Organizer
      20th Joint Glycobiology Meeting
    • Place of Presentation
      Cologne, Germany
    • Year and Date
      2009-11-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis of the unique starfish ganglioside AG2 pentasaccharide using silylene/oxazolidinone double-locked building blocks2009

    • Author(s)
      Shinya Hanashima
    • Organizer
      Japanese-Giessen-GlycoWorkshop
    • Place of Presentation
      Giessen, Germany
    • Year and Date
      2009-11-07
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Synthesis and biological function of the unique starfish ganglioside AG2 pentasaccharide Austria/Japan seminar on Comparative Glycobiology and Development Biology2009

    • Author(s)
      Shinya Hanashima
    • Place of Presentation
      葉山
    • Year and Date
      2009-09-21
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis and biological function of the unique starfish ganglioside AG2 pentasaccharide2009

    • Author(s)
      花島慎弥
    • Organizer
      Austria/Japan seminar on Comparative Glycobiology and Development Biology
    • Place of Presentation
      神奈川、葉山
    • Year and Date
      2009-09-21
    • Related Report
      2009 Annual Research Report
  • [Presentation]2009

    • Author(s)
      花島慎弥
    • Organizer
      三環性シアル酸供与体を用いた効率的シアリル化の検討日本糖質学会年会
    • Place of Presentation
      高山
    • Year and Date
      2009-09-11
    • Related Report
      2010 Final Research Report
  • [Presentation] 三環性シアル酸供与体を用いた効率的シアリル化の検討2009

    • Author(s)
      花島慎弥
    • Organizer
      日本糖質学会年会
    • Place of Presentation
      岐阜、高山
    • Year and Date
      2009-09-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] 新規シアル酸供与体を用いたガングリオシドAG2糖鎖の合成2008

    • Author(s)
      花島慎弥
    • Organizer
      有機合成化学協会関東支部会新潟シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2008-11-30
    • Related Report
      2010 Final Research Report
  • [Presentation] 新規シアル酸供与体を用いたガングリオシドAG2糖鎖の合成2008

    • Author(s)
      花島慎弥
    • Organizer
      有機合成化学協会 関東支部会新潟シンポジウム
    • Place of Presentation
      新潟大学
    • Year and Date
      2008-11-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] シアル酸を糖鎖中央部にもつガングリオシドAG-2五糖の合成研究2008

    • Author(s)
      花島慎弥
    • Organizer
      第28回日本糖質学会年会
    • Place of Presentation
      筑波
    • Year and Date
      2008-08-19
    • Related Report
      2010 Final Research Report
  • [Presentation] シアル酸を糖鎖中央部にもつガングリオシドAG-2五糖の合成研究2008

    • Author(s)
      花島慎弥
    • Organizer
      第28回日本糖質学会年会
    • Place of Presentation
      筑波国際会議場
    • Year and Date
      2008-08-19
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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