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2012 Fiscal Year Final Research Report

Approach toward chemical synthesis of highly branched glycans of glycoconjugate

Research Project

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Project/Area Number 22510243
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionThe Institute of Physical and Chemical Research

Principal Investigator

ISHIWATA Akihiro  独立行政法人理化学研究所, 伊藤細胞制御化学研究室, 専任研究員 (70342748)

Project Period (FY) 2010 – 2012
Keywords糖鎖合成 / オリゴ糖 / 立体選択的合成 / グリコシル化 / 収斂的合成 / 複合糖質糖鎖 / 多分岐糖鎖
Research Abstract

Long-distance intramolecular aglycon delivery (IAD) was conducted to construct 1.2-cis glycosidic linkages whose stereoselective synthesis is one of the most difficult. The convergent strategy toward tetrabranched docosa- and hentriaconta-saccharide arabinan from Mycobacterial arabinan and the strategy for construction of highly branched structure have been studied. IAD method has been improved to achieve the syntheses of core structure of N-glycan and antifreeze glycan fragment from Upis ceramboides. The concentration effect on various factors of accelerated O-glycosylation when the reaction solvent was frozen has been studied.

  • Research Products

    (30 results)

All 2013 2012 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (20 results) Remarks (3 results)

  • [Journal Article] Biotechnological approaches toward the synthesis of eukaryotic N-linked glycoprotein2012

    • Author(s)
      Ishiwata, A.
    • Journal Title

      Trends in Glycosci. Glycotech

      Volume: 24 Pages: 225-227

    • DOI

      DOI:10.4052/tigg.24.225

    • Peer Reviewed
  • [Journal Article] Accelerated O-glycosylation under frozen conditions and its application to the synthesis of complex glycans2012

    • Author(s)
      Ishiwata, A.; Sakurai, A.; Ito, Y.
    • Journal Title

      Trends in Glycosci. Glycotech

      Volume: 24 Pages: 179-189

    • DOI

      DOI:10.4052/tigg.24.179

    • Peer Reviewed
  • [Journal Article] 分子内アグリコン転移反応と立体選択的糖鎖合成への応用2012

    • Author(s)
      石渡明弘, 伊藤幸成
    • Journal Title

      有機合成化学協会誌

      Volume: 70 Pages: 382-394

    • DOI

      DOI:10.5059/yukigoseikyokaishi.70.382

    • Peer Reviewed
  • [Journal Article] Synthetic study and structural analysis of the antifreeze agent xylomannan from Upis ceramboides2011

    • Author(s)
      Ishiwata, A.; Sakurai, A.; Nishimiya, Y.; Tsuda, S.; Ito, Y.
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 19524-19535

    • DOI

      DOI:10.1021/ja208528c

    • Peer Reviewed
  • [Journal Article] Drug-resistant tuberculosis and inhibition of biosynthetic enzymes for polysaccharides in mycobacterial cell wall2011

    • Author(s)
      Ishiwata, A.
    • Journal Title

      Trends in Glycosci. Glycotech

      Volume: 23 Pages: 106-107

    • DOI

      DOI:10.4052/tigg.23.106

    • Peer Reviewed
  • [Journal Article] Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall2011

    • Author(s)
      Ishiwata, A.; Ito, Y.
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 2275-2291

    • DOI

      DOI:10.1021/ja109932t

    • Peer Reviewed
  • [Journal Article] Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions2010

    • Author(s)
      Ishiwata, A.; Sakurai, A.; Durr, K.; Ito, Y.
    • Journal Title

      Bioorg. Med. Chem

      Volume: 18 Pages: 3678-3695

    • DOI

      DOI:10.1016/j.bmc.2010.04.013

    • Peer Reviewed
  • [Presentation] 分子内アグリコン転移反応を利用した、β-L-アラビノフラノシド誘導体の合成研究2013

    • Author(s)
      石渡明弘, Sophon Kaeothip, 伊藤幸成
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      20130324-27
  • [Presentation] 分子内アグリコン転移反応を利用した、マンノースキャッピングされたアラビナン構造の構築検討2013

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      20130322-25.
  • [Presentation] Stereoselective Constructions of Complex Bacterial Glycans2012

    • Author(s)
      Ishiwata, A.; Ito, Y.
    • Organizer
      4th Asian Communication for Glycobiology and Glycotechnology
    • Place of Presentation
      Jeju, Korea(Invited)
    • Year and Date
      20121028-31
  • [Presentation] NAPエーテルを介した分子内アグリコン転移反応の応用:1,2-cis グリコシドを含む、キシロマンナンフラグメントの立体選択的構築2012

    • Author(s)
      石渡明弘, 櫻井絢花, 伊藤幸成
    • Organizer
      第31回日本糖質学会年会
    • Place of Presentation
      鹿児島
    • Year and Date
      20120917-20
  • [Presentation] Application of NAP ether-mediated intramolecular aglycon delivery to stereoselective construction of xylomannan fragment containing 1,2-cis glycosides2012

    • Author(s)
      Ishiwata, A.; Sakurai, A.; Ito, Y.
    • Organizer
      26^<th> International Carbohydrate Symposium
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      20120722-27
  • [Presentation] 結核菌由来アラビナン4分岐31糖の合成研究2012

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      20120325-29
  • [Presentation] 分子内アグリコン転移反応を利用した、Upis ceramboides 由来キシロマンナン不凍多糖の合成研究と構造解析2012

    • Author(s)
      石渡明弘, 櫻井絢花, 伊藤幸成
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      20120322-26
  • [Presentation] 新規不凍活性物質キシロマンナンの合成研究と構造解2012

    • Author(s)
      石渡明弘, 櫻井絢花, 伊藤幸成
    • Organizer
      GlycoTOKYO2012シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-11-17
  • [Presentation] Synthetic study of pseudaminic acid from bacterial glycoprotein2011

    • Author(s)
      Lee, Y. J.; Kubota, A.Lee, Y. J.; Kubota, A.; Ishiwata, A.; Ito, Y.
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡(poster &amp; short talk)
    • Year and Date
      20110929-1001
  • [Presentation] Strategies toward stereoselective construction of complex bacterial glycans2011

    • Author(s)
      Ishiwata, A.
    • Organizer
      14th Asian Chemical Congress 2011
    • Place of Presentation
      Bangkok, Thailand(Invited)
    • Year and Date
      20110905-08
  • [Presentation] 結核菌細胞壁多糖アラビナンの合成研究2011

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      第30回日本糖質学会年会
    • Place of Presentation
      長岡(poster)
    • Year and Date
      20110711-13
  • [Presentation] 結核菌由来アラビナン分岐7糖フラグメント構築へ向けた分子内アグリコン転移反応の応用2011

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      20110326-29
  • [Presentation] 結核菌由来アラビナン8糖フラグメントの合成とフラグメントカップリング2011

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都
    • Year and Date
      20110325-28
  • [Presentation] 細菌由来複合糖質糖鎖の合成研究2011

    • Author(s)
      石渡明弘
    • Organizer
      GlycoTOKYO2011シンポジウム,
    • Place of Presentation
      和光(招待講演)
    • Year and Date
      2011-12-09
  • [Presentation] 細菌由来複合糖質糖鎖の合成研究2011

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      京都大学グローバル COE-基幹研究所 合同シンポジウム
    • Place of Presentation
      和光(poster)
    • Year and Date
      2011-01-28
  • [Presentation] Synthetic study of mycobacterial arabinan2010

    • Author(s)
      Ishiwata, A.; Ito, Y.
    • Organizer
      PACIFICHEM2010
    • Place of Presentation
      Hawaii, USAGlycoTOKYO2010 シンポジウム,
    • Year and Date
      20101215-20
  • [Presentation] Accelerated glycosylation under frozen conditions: Effect on stereoselectivity and velocity of O-glycosylation2010

    • Author(s)
      Ishiwata, A.; Sakurai, A.; Durr, K.; Ito, Y.
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      20101215-20
  • [Presentation] 細菌由来複合糖質糖鎖の合成研究2010

    • Author(s)
      石渡明弘
    • Organizer
      第59回高分子討論会
    • Place of Presentation
      札幌,(招待講演)
    • Year and Date
      20100915-17
  • [Presentation] Synthetic study of mycobacterial arabinan2010

    • Author(s)
      Ishiwata, A.; Ito, Y.
    • Organizer
      International Carbohydrate Symposium
    • Place of Presentation
      Tokyo
    • Year and Date
      20100801-06
  • [Presentation] NAP エーテルを介する分子内アグリコン転移反応を利用した、β-マンノシル化の検討2010

    • Author(s)
      石渡明弘, 櫻井絢花, 李龍柱, 伊藤幸成
    • Organizer
      GlycoTOKYO2010 シンポジウム
    • Place of Presentation
      東京(poster)
    • Year and Date
      2010-11-27
  • [Remarks] Org. Biomol. Chem. 2010, 8, 3596-3608に掲載さ れた高選択的グリコシル化反応に関する論文 (論文 7)は表紙に採用された.

  • [Remarks] J. Am. Chem. Soc. 2011, 133, 2275-2291.に掲載さ れた結核菌多糖の合成に関する論文 (論文 6)はRIKEN RESEARCH で紹介された。

    • URL

      http://www.rikenresearch.riken.jp/jpn/research/6871

  • [Remarks] J. Am. Chem. Soc. 2011, 133, 19524-19535.に掲載さ れた不凍糖の合成と構造解析に関する論文 (論文 4)はAsian Research News, 2012. 12.で紹介された。また、RIKEN RESEARCH で紹介された。

    • URL

      http://www.rikenresearch.riken.jp/eng/research/6592

URL: 

Published: 2014-08-29  

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