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The shortest synthetic route of polymeric glycomaterials through a one-pot reaction system based on organic reaction and enzymatic reaction

Research Project

Project/Area Number 24350052
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
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) 2012-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,070,000 (Direct Cost: ¥13,900,000、Indirect Cost: ¥4,170,000)
Fiscal Year 2015: ¥6,110,000 (Direct Cost: ¥4,700,000、Indirect Cost: ¥1,410,000)
Fiscal Year 2014: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2013: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2012: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Keywords化学酵素合成 / 糖タンパク質 / ヒトミルクオリゴ糖 / 糖オキサゾリン / 脱水縮合剤 / 熱応答性高分子 / 糖転移反応 / 糖加水分解酵素 / 化学酵素合成法 / トラスツズマブ / モノクローナル抗体 / 糖鎖 / 抗体医薬品 / 変異型酵素 / ラクトN-ビオース / ラクトN-テトラオース / ポリアクリルアミド / キトオリゴ糖 / 配糖化 / 酵素触媒 / ワンポット化 / SGオリゴ糖 / CDMBI
Outline of Final Research Achievements

A basic research on the development of one-pot glycosylation based on chemical reaction and enzymatic reaction has been carried out. An oligosaccharide having an N-acetylglucosamine moiety at the reducing end was converted to the corresponding sugar oxazoline derivative in more than 95% yields by using 2-chloroimidazolinium salt or 2-chlorobenzimidazolium salt as dehydrating agents. As a model compound for controlling enzyme activities, several thermosensitive glycopolymers based on poly(N-isopropylacrylamide) having a chitooligosaccharide was prepared. Based on these results,glycoproteins having a definite oligosaccharide as well as human milk oligosaccharides have successfully been prepared in good yields.

Report

(5 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (31 results)

All 2016 2015 2014 2013 2012 2011 Other

All Journal Article (15 results) (of which Peer Reviewed: 13 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (8 results) (of which Invited: 7 results) Book (5 results) Remarks (3 results)

  • [Journal Article] Glycoengineered Monoclonal Antibodies with Homogeneous Glycan (M3, G0, G2, and A2) using a chemoenzymatic approach have different affinities for FcgammaRIIIa and variable antibody-dependent cellular cytotoxicity activities2016

    • Author(s)
      M. Kurogochi, M. Mori, K. Osumi, M. Tojino, S. Sugawara, S. Takashima, Y. Hirose, W. Tsukimura, M. Mizuno, J. Amano, A. Matsuda, M. Tomita, A. Takayanagi, S. Shoda, T. Shirai
    • Journal Title

      PLOS ONE

      Volume: July 22

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enzymes as Green Catalysts for Precision Macromolecular Synthesis2016

    • Author(s)
      Shin-ichiro Shoda, Hiroshi Uyama, Jun-ichi Kadokawa, Shunsaku Kimura, Shiro Kobayashi
    • Journal Title

      Chemical Reviews

      Volume: 116 Issue: 4 Pages: 2307-2413

    • DOI

      10.1021/acs.chemrev.5b00472

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The One-step Preparation of Sugar Oxazoline Enables the Synthesis of Glycoprotein Having a Definite Structure2015

    • Author(s)
      M. Noguchi, A. Kobayashi, S. Shoda
    • Journal Title

      Trends in Glycoscience and Glycotechnology

      Volume: 27 Issue: 158 Pages: E35-E42

    • DOI

      10.4052/tigg.1505.2E

    • NAID

      130005110345

    • ISSN
      0915-7352, 1883-2113
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glytcosyl Donors2015

    • Author(s)
      T. Tanaka, N. Kimuta, Y. Kimura, S. Shoda
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 6 Pages: 846-848

    • DOI

      10.1246/cl.150201

    • NAID

      130005074607

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [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 Pages: 1074-1078

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

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

      Cellulose Communications

      Volume: 20 Pages: 20-24

    • Related Report
      2013 Annual Research 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 Annual Research 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 Issue: 10 Pages: 1235-1237

    • DOI

      10.1246/cl.130646

    • NAID

      10031201322

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] To Make a Glycoprotein with a Definite Molecular Weight2013

    • Author(s)
      S. Shoda, A. Kobayashi, M. Noguchi
    • Journal Title

      有機合成化学協会誌

      Volume: 71 Pages: 1252-1258

    • Related Report
      2013 Annual Research Report
  • [Journal Article] A dimethoxytriazine type glycosyl donor enables facile chemo-enzymatic route towardα-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin2012

    • Author(s)
      Masato Noguchi, Miwa Nakamura, Ayaka Ohno, Tomonari Tanaka, Atsushi Kobayashi, Masaki Ishihara, Masaya Fujita, Akiko Tsuchida, Mamoru Mizuno, and Shin-ichiro Shoda
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 45 Pages: 5560-5562

    • DOI

      10.1039/c2cc30946g

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-pot chemo-enzymatic route to chitoheptaose via specific transglycosylation of chitopentaose-oxazoline on chitinase-template2012

    • Author(s)
      Naoki Yoshida, Tomonari Tanaka, Masato Noguchi, Atsushi Kobayashi, Kumiko Ishikura, Tatsuya Ikenuma, Hiromu Seno, Takeshi Watanabe, Michinari Kohri, and Shin-ichiro Shoda
    • Journal Title

      Chemistry Letters

      Volume: 41 Issue: 7 Pages: 689-690

    • DOI

      10.1246/cl.2012.689

    • NAID

      10030786354

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Practical One-Step Synthesis of 1,2-Oxazoline Derivatives from Unprotected Sugars and Its Application to Chemoenzymatic β-N-Acetylglucosa minidation of Disialo-oligosaccharide2012

    • Author(s)
      M. Noguchi, T. Fujieda, W.C. Huang, M. Ishihara, A. Kobayashi, S. Shoda
    • Journal Title

      Helvetica Chimica Acta

      Volume: 95 Pages: 1928-1936

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 4,6-Dimethoxy-1,3,5-triazin-2-ylβ-D-glycosaminides : Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-β-D-glucosaminidase from Amycolatopsis orientalis2011

    • Author(s)
      Tomonari Tanaka, Tomonori Wada, Masato Noguchi, Masaki Ishihara, Atsushi Kobayashi, Takayuki Ohnuma, Tamo Fukamizo, Ryszard Brzezinski, Shin-ichiro Shoda
    • Journal Title

      Journal of Carbohydrate Chemistry

      Volume: 31 Issue: 8 Pages: 634-646

    • DOI

      10.1080/07328303.2012.698437

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] グライコプロセスケミストリー  -多糖バイオマス資源の有効利用に向けて-2015

    • Author(s)
      正田晋一郎
    • Organizer
      高分子学会
    • Place of Presentation
      東北大学川内キャンパス(宮城県・仙台市)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
    • Invited
  • [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] Protection-free glycosylation of oligosaccharides2013

    • Author(s)
      S. Shoda
    • Organizer
      European-Japanese Workshop on Cellulose and Functionl Polysaccharides 2012
    • Place of Presentation
      東京(招待講演)
    • Year and Date
      2013-10-03
    • Related Report
      2012 Annual Research Report
  • [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 Annual Research 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 Annual Research 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 Annual Research Report
    • Invited
  • [Book] White Biotechnology for Sustainable Chemistry2016

    • Author(s)
      S. Shoda, A. Kobayashi, S. Kobayashi
    • Total Pages
      417
    • Publisher
      Royal Society of Chemistry
    • Related Report
      2015 Annual Research Report
  • [Book] Glycosicence: Biology and Medicine2015

    • Author(s)
      S. Shoda, A. Kobayashi, M. Noguchi
    • Total Pages
      1568
    • Publisher
      Springer Reference
    • Related Report
      2015 Annual Research Report
  • [Book] 糖鎖の新機能開発・応用ハンドブック 創薬・医療から食品開発まで2015

    • Author(s)
      正田晋一郎,小林厚志,野口真人
    • Total Pages
      628
    • Publisher
      NTS
    • Related Report
      2015 Annual Research Report
  • [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2015

    • Author(s)
      正田晋一郎,小林厚志,野口真人
    • Total Pages
      260
    • Publisher
      シーエムシー出版
    • Related Report
      2014 Annual Research Report
  • [Book] 化学2012

    • Author(s)
      野口真人、正田晋一郎
    • Publisher
      化学同人
    • Related Report
      2012 Annual Research Report
  • [Remarks] 糖鎖均一化抗HER2ヒト化モノクローナル抗体の創製に成功

    • URL

      http://www.tohoku.ac.jp/japanese/2015/11/press20151125-03.html

    • Related Report
      2015 Annual Research 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/toukouronbun/toukouronbun.html

    • Related Report
      2014 Annual Research Report
  • [Remarks]

    • URL

      http://www.tohoku.ac.jp/japanese/2011/02press20110208-2.html

    • Related Report
      2012 Annual Research Report

URL: 

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

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