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2011 Fiscal Year Final Research Report

One-step Synthesis and Polymerization of Glyco-monomers in Aqueous Media without Using Protecting Groups

Research Project

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Project/Area Number 20350051
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer chemistry
Research InstitutionTohoku University

Principal Investigator

SHODA Shin-ichiro  東北大学, 大学院・工学研究科, 教授 (10143364)

Project Period (FY) 2008 – 2011
Keywords保護基 / 配糖化 / 糖質 / 一段階合成
Research Abstract

Sugar molecules have many hydroxyl groups. In order to derivatize sugar molecules, the hydroxyl groups must be protected. In the present research, we have developed a completely different synthetic process of glycol-monomers without using any protecting groups in aqueous media. The resulting glyco-monomers can be utilized as starting materials of various glyco-polymers.

  • Research Products

    (33 results)

All 2012 2011 2010 2009 2008 Other

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (7 results) Book (6 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Crystal Structures of Glycoside Hydrolase's Family 51 a-L-Arabinofuranosidase from Thermotoga maritime2012

    • Author(s)
      D. H. Im, K. Kimura, F. Hayasaka, T. Tanaka, M. Noguchi, A. Kobayashi, S. Shoda, K. Miyazaki, T. Wakagi, S. Fushinobu
    • Journal Title

      Biosci. Biotechnol. Biochem.

      Volume: 76 Pages: 423-428

    • Peer Reviewed
  • [Journal Article] α-N-Acetylglalctosaminidase from Infant-associated Bifid bacteria Belonging to Novel Glycoside Hydrolase Family 129 is Implicated in Alternative Mucin Degradation Pathway2012

    • Author(s)
      M. Kiyohara, T. Nakatomi, S. Kurihara, S. Fushinobu, H. Suzuki, T. Tanaka, S. Shoda, M. Kitaoka, T. Katayama, K. Yamamoto, H. Ashida
    • Journal Title

      J. Biol. Chem.

      Volume: 287 Pages: 693-700

    • Peer Reviewed
  • [Journal Article] Direct Dehydrative Pyridylthio Glycosidation of Unprotected Sugars in Aqueous Media Using 2-Chloro-1, 3-dimethylimidazolinium Chloride as a Condensing Agent2011

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

      Chem. Asian J.

      Volume: 6 Pages: 1867-1885

    • Peer Reviewed
  • [Journal Article] Novel Dialkoxytriazine-type Glycosyl Donors for Cellulase-catalysed Lactosylation2010

    • Author(s)
      T. Tanaka, M. Noguchi, K. Watanabe, T. Misawa, M. Ishihara, A. Kobayashi, S. Shoda
    • Journal Title

      Org. Biomol. Chem.

      Volume: 8 Pages: 5126-5132

    • Peer Reviewed
  • [Journal Article] Efficient transfer of sialo-oligosaccharide onto proteins by combined use of a glycosynthase-like mutant of Mucor hiemalis endoglycosidase and synthetic sialo-complex-type sugar oxazoline2010

    • Author(s)
      M. Umekawa, T. Higashiyama, Y. Koga, T. Tanaka, M. Noguchi, A. Kobayashi, S. Shoda, W. Huang, L. X. Wang, H. Ashida, K. Yamamoto
    • Journal Title

      Biochim. Biophys. Acta

      Volume: 1800 Pages: 1203-1209

    • Peer Reviewed
  • [Journal Article] Synthesis of Non-natural Xyloglucans by Polycondensation of 4, 6-Dimethoxy-1, 3, 5-triazin-2-yl Oligosaccharide Monomers Catalyzed by Endo-.-1, 4-glucanase2010

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

      Macromol. Symp.

      Volume: 297 Pages: 200-209

    • Peer Reviewed
  • [Journal Article] 4, 6-Dimethoxy-1, 3, 5-triazine oligoxyloglucans : Novel one-step preparable substrates for studying action of endo-.-1, 4-glucanase III from Trichoderma reesei2010

    • Author(s)
      A. Kobayashi, T. Tanaka, K. Watanabe, M. Ishihara, M. Noguchi, H. Okada, Y. Morikawa, S. Shoda
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 20 Pages: 3588-3591

    • Peer Reviewed
  • [Journal Article] Dimethoxy Triazine Glycosides as New Glycosyl Donors for Chemo-enzymatic Synthesis of Oligosaccharides2009

    • Author(s)
      T. Tanaka, A. Kobayashi, M. Noguchi, K. Kimura, K. Watanabe, S. Shoda
    • Journal Title

      J. Appl. Glycosci.

      Volume: 56 Pages: 83-88

    • Peer Reviewed
  • [Journal Article] One-step conversion of unprotected sugars to b-glycosyl azides using 2-chloroimidazolinium salt in aqueous solutions2009

    • Author(s)
      T. Tanaka, H. Nagai, M. Noguchi, A. Kobayashi, S. Shoda
    • Journal Title

      Chem. Commun.

      Pages: 3378-3379

    • Peer Reviewed
  • [Journal Article] Synthesis of artificial oligosaccharides by polycondensation of 2'-O-methyl cellobiosyl fluoride and mannoxyl-glucosyl fluoride catalyzed by cellulase2009

    • Author(s)
      R. Izumi, Y. Suzuki, Y. Shimizu, M. Fujita, M. Ishihara, M. Noguchi, A. Kobayashi, S. Shoda
    • Journal Title

      Transworld Research Network

      Volume: 37/661 Pages: 45-67

    • Peer Reviewed
  • [Journal Article] Direct Transformation of Unprotected Sugars to Aryl 1-Thio-.-glycosides in Aqueous Media Using 2-Chloro-1, 3-dimethylimidazolinium Chloride2009

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

      Chem. Lett.

      Volume: 38 Pages: 458-459

    • Peer Reviewed
  • [Journal Article] Direct synthesis of 1, 6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1, 3-dimethylimidazolinium chloride2009

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

      Tetrahedron Lett.

      Volume: 50 Pages: 2154-2157

    • Peer Reviewed
  • [Journal Article] Efficient Synthesis of Sugar Oxazolines from Unprotected N-Aceyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water2009

    • Author(s)
      M. Noguchi, T. Tanaka, H. Gyakushi, A. Kobayashi, S. Shoda
    • Journal Title

      J. Org. Chem.

      Volume: 74 Pages: 2210-2212

    • Peer Reviewed
  • [Journal Article] A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis : 4, 6-dimethoxy-1, 3, 5-triazin-2-yl glycoside2008

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

      Chem. Commun.

      Pages: 2016-2018

    • Peer Reviewed
  • [Journal Article] A dimethoxytriazine type glycosyl donor enables facile chemo-enzymatic route toward .-linked N-acetylglucosaminyl galactose disaccharide unit from gastric mucin

    • Author(s)
      M. Noguchi, M. Nakamura, A. Ohno, T. Tanaka, A. Kobayashi, M. Ishihara, M. Fujita, A. Tsuchida, M. Mizuno, S. Shoda
    • Journal Title

      Chem. Commun

      Volume: (印刷中)

    • Peer Reviewed
  • [Journal Article] One-Pot Chemo-Enzymatic Route to Chitoheptaose via Specific Transglycosylation of Chitopentaose Oxazoline on Chitinase-Template

    • Author(s)
      N. Yoshida, T. Tanaka, M. Noguchi, A. Kobayashi, K. Ishikura, T. Ikenuma, H. Seno, T. Watanabe, M. Kohri, S. Shoda
    • Journal Title

      Chem. Lett

      Volume: (印刷中)

    • Peer Reviewed
  • [Journal Article] 4, 6-Dimethoxy-1, 3, 5-triazin-2-yl .-D-glycosaminides : Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-Dglucosaminidase from Amycolatopsis oriental is

    • Author(s)
      T. Tanaka, T. Wada, M. Noguchi, M. Ishihara, A. Kobayashi, T. Ohnuma, T. Fukamizo, R. Brzezinski, S. Shoda
    • Journal Title

      J. Carbohydr. Chem

      Volume: (印刷中)

    • Peer Reviewed
  • [Presentation] Protection-Free Glycosylations2011

    • Author(s)
      S. Shoda
    • Organizer
      The 3rd Asian Communications of Glycobiology and Glycotechnology
    • Place of Presentation
      上海 (中国)
    • Year and Date
      2011-10-28
  • [Presentation] Architecture of Sugar-Materials Based on Concept of Glyco-Chemistry Cycle2011

    • Author(s)
      S. Shoda
    • Organizer
      6th International Symposium on Chemical-Environmental-Biomedical Technology
    • Place of Presentation
      Hsinchu (Taiwan, R. O. C)
    • Year and Date
      2011-09-06
  • [Presentation] Facile Chemo-Enzymatic Glycosylating Process through Dialkoxytriazine (DAT)Synthetic Intermediate2010

    • Author(s)
      S. Shoda
    • Organizer
      International Carbohydrate Symposium
    • Place of Presentation
      東京
    • Year and Date
      2010-08-03
  • [Presentation] New Frontier of Chemo-enzymatic Glycosylation2009

    • Author(s)
      S. Shoda
    • Organizer
      4th Annual Meeting of the Korean Society for Glycoscience
    • Place of Presentation
      Daejeon, Korea
    • Year and Date
      2009-11-13
  • [Presentation] One-pot Chemo-enzymatic Synthesis of Polysaccharides by Using Novel Glycosyl Donors2009

    • Author(s)
      S. Shoda, A. Kobayashi, M. Noguchi, T. Tanaka, K. Ishikura
    • Organizer
      Jpn-Euro Cellulose Workshop
    • Place of Presentation
      Hamburg, Germany
    • Year and Date
      2009-09-18
  • [Presentation] Novel glycosyl donors for enzyme-catalyzed oligosaccharide synthesis2009

    • Author(s)
      S. Shoda, T. Tanaka, M. Noguchi, A. Kobayashi
    • Organizer
      237th ACS National Meeting
    • Place of Presentation
      Salt Lake City, USA
    • Year and Date
      2009-03-24
  • [Presentation] One-pot chemo-enzymatic glycosylation2008

    • Author(s)
      S. Shoda
    • Organizer
      236th ACS National Meeting
    • Place of Presentation
      Philadelphia, USA
    • Year and Date
      2008-08-21
  • [Book] バイオ医薬品開発における糖鎖技術2011

    • Author(s)
      正田晋一郎
    • Total Pages
      96-105
    • Publisher
      シーエムシー出版
  • [Book] 酵素利用技術体系2010

    • Author(s)
      正田晋一郎, 小林厚志, 野口真人
    • Total Pages
      408-413
    • Publisher
      NTS
  • [Book] 複合糖質の化学と最新応用技術2009

    • Author(s)
      野口真人, 田中知成, 小林厚志, 正田晋一郎
    • Total Pages
      83-89
    • Publisher
      シーエムシー出版
  • [Book] セルロース利用技術の最先端2008

    • Author(s)
      正田晋一郎, 小林厚志, 野口真人
    • Total Pages
      77-82
    • Publisher
      シーエムシー出版
  • [Book] Handbook of Chemical Glycosylation2008

    • Author(s)
      S. Shoda
    • Total Pages
      29-59
    • Publisher
      Wiley-VCH
  • [Book] Experimental Glycoscience2008

    • Author(s)
      S. Shoda
    • Total Pages
      169-172
    • Publisher
      Springer
  • [Remarks]

    • URL

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

  • [Patent(Industrial Property Rights)] N-アセチルグルコサミンがαで結合した糖誘導体の調製方法2011

    • Inventor(s)
      藤田雅也、土田明子、正田晋一郎、田中知成、明石景泰
    • Industrial Property Rights Holder
      財団法人野口研究所
    • Industrial Property Number
      特許、特願2011-190079
    • Filing Date
      2011-08-31
  • [Patent(Industrial Property Rights)] N-アセチルグルコサミンがαで結合した糖誘導体の調製方法2010

    • Inventor(s)
      藤田雅也、土田明子、正田晋一郎、田中知成
    • Industrial Property Rights Holder
      財団法人野口研究所
    • Industrial Property Number
      特許、特願2010-054874
    • Filing Date
      2010-03-11

URL: 

Published: 2013-07-31  

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