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Glycosylation without adding any acid catalysts -Synthesis and organization of impossible oligosaccharide glycolipids-

Research Project

Project/Area Number 25620092
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research InstitutionTohoku University

Principal Investigator

SHODA Shin-ichiro  東北大学, 工学(系)研究科(研究院), 教授 (10143364)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords糖脂質 / トリアジン誘導体 / 水素添加 / グリコシル化 / 立体選択性 / オリゴ糖 / 酸触媒 / アノマー直接活性化 / 糖トリアジン誘導体 / 無保護糖 / 選択的アノマー位活性化 / 接触還元 / αグリコシド / キトオリゴ糖 / キシログルカンオリゴ糖 / アノマー位 / 脱水縮合剤 / 直接活性化
Outline of Final Research Achievements

Glycolipids play important roles in cell processes such as bio-recognition on the cell membranes.Chemically, amphiphilic glycolipids can self-assemble into 3D architectures that are attractive smart hydrogels for biomolecular microarrays and dug delivery. Meanwhile, vinyl-contained glycolipid is potential monomer for the synthesis of glycopolymer, synthetic polymer with saccharide pendants, and has received considerable attention in the fields of material science and biomedicine. We have developed a reductive synthetic method towards glycolipid by the alcoholysis of the one-step preparable glycosyl donor,4,6-dibenzyloxy-1,3,5-triazin-2-yl glycosides under reductive conditions, without adding any acid catalysts. Through this reaction, glycosidic bonds between oligosaccharides and alcohols were constructed with the site specific activation at the reducing end under extremely mild reaction conditions, which had been impossible to carry out for a long time.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (15 results)

All 2014 2013 Other

All Journal Article (6 results) (of which Peer Reviewed: 5 results) Presentation (6 results) (of which Invited: 6 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Protecting -Group-Free Synthesis of Glycopolymers Bearing Sialyloligosaccharide and Their High Binding with the Influenza Virus2014

    • Author(s)
      T. Tanaka, H. Ishitani, Y. Miura, K. Oishi, T. Takahashi, T. Suzuki, S. Shoda, Y. Kimura
    • Journal Title

      ACS Macromol. Lett

      Volume: 3

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Protecting-Group-Free Synthesis of Glycopolymers Bearing Thioglycosides via One-Pot Monomer Synthesis from Free Saccharides2014

    • Author(s)
      T. Tanaka, G. Inoue, S. Shoda, Y. Kimura
    • Journal Title

      J. Polym. Sci. Part A

      Volume: 52 Pages: 3513-3520

    • DOI

      10.1002/pola.27417

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of Oligosaccharide-Poly(L-lactide) Conjugates Forming Nanoparticles with Saccharide Core and Shell2013

    • Author(s)
      T. Tanaka, H. Fukuhara, S. Shoda, Y. Kimura
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 2 Pages: 197-199

    • DOI

      10.1246/cl.2013.197

    • NAID

      130004426860

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Reducing End-Specific Fluorescence Labeling of Oligosaccharides2013

    • Author(s)
      N. Yoshida, S. Shoda
    • Journal Title

      Cellulose Communications

      Volume: 20

    • Related Report
      2013 Research-status Report
  • [Journal Article] Direct Introduction of Detachable Fluorescent Tag into Oligosaccharides2013

    • Author(s)
      N. Yoshida, T. Fujieda, A. Kobayashi, M. Ishihara, M. Noguchi, S. Shoda
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 9 Pages: 1038-1039

    • DOI

      10.1246/cl.130379

    • NAID

      10031194333

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Protection-free Synthesis of Alkyl Glycosides under Hydrogenolytic Conditions2013

    • Author(s)
      M. Ishihara, Y. Takagi, G. Li, M. Noguchi, S. Shoda
    • Journal Title

      Chemistry Letters

      Volume: 42

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Specific Anomeric Activation in Water2014

    • Author(s)
      S. Shoda
    • Organizer
      2014 Japan-Euro Cellulose Workshop
    • Place of Presentation
      Berlin(ドイツ)
    • Year and Date
      2014-10-13 – 2014-10-16
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] オリゴ糖合成における基質と酵素のデザイン2014

    • Author(s)
      正田晋一郎
    • Organizer
      日本応用糖質科学会
    • Place of Presentation
      朱鷺メッセ(新潟県新潟市)
    • Year and Date
      2014-09-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 分子量のそろった糖タンパク質をつくる  -水中におけるオリゴ糖の直接活性化技術ー2014

    • Author(s)
      正田晋一郎
    • Organizer
      9学協会東北地方大会
    • Place of Presentation
      山形大学工学部(山形県米沢市)
    • Year and Date
      2014-09-21
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] オリゴ糖脂質を合成する新手法の開発2013

    • Author(s)
      正田晋一郎
    • Organizer
      糖鎖科学コンソーシアムシンポジウム
    • Place of Presentation
      仙台
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 水中における最短グリコシル化プロセスを目指して2013

    • Author(s)
      正田晋一郎
    • Organizer
      繊維学会東北北海道支部特別企画日韓親善学術講演会
    • Place of Presentation
      福島
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 現場で役立つグリコシル化の基本2013

    • Author(s)
      正田晋一郎
    • Organizer
      有機合成化学協会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Book] グリコシルアジドの一段階合成  クリックケミストリー  基礎から実用まで2014

    • Author(s)
      正田晋一郎,小林厚志,野口真人
    • Publisher
      シーエムシー出版
    • Related Report
      2014 Annual Research Report
  • [Book] 有機合成化学協会誌2013

    • Author(s)
      S. Shoda, A. Kobayashi, M. Noguchi
    • Publisher
      To Make a Glycoprotein with a Definite Molecular Weight
    • Related Report
      2013 Research-status Report
  • [Remarks] 東北大学大学院工学研究科バイオ工学専攻機能高分子化学分野

    • URL

      http://www.che.tohoku.ac.jp/~poly/

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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