Preparative synthesis of polysaccharide by using direct activation method

• Project/Area Number: 21750109
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Polymer chemistry
• Research Institution: Tohoku University
• Principal Investigator: NOGUCHI Masato 東北大学, 大学院・工学研究科, 助教 (10400285)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: 酵素触媒重合反応 / 多糖合成 / 活性化糖誘導体 / 大量合成 / 化学-酵素合成 / 糖オキサゾリン誘導体 / DMT-グリコシドモノマー

Research Abstract

To obtain the polysaccharide consisting of definite structure, a preparative synthetic method for monomer and enzymatic polymerization reaction were investigated. We have achieved direct synthesis of monomer substrate from free saccharide and successively obtained 1. 8g amounts of monomer. We have also developed a novel condensing agent for the direct synthesis of oxazoline derivative in sufficient yield. One-pot polycondensation reaction occurred by using of novel condensing agent and chitinase.

Research Products

• [Journal Article] Crystal Structures of Glycoside Hydrolase Family 51.-L-Arabinofuranosidase from Thermotoga maritime. (2012)
  • Author(s): Im, D. ; Kimura, K. ; Hayasaka, F. ; Tanaka, T. ; Noguchi, M. ; Kobayashi, A. ; Shoda, S. ; Miyazaki, K. ; Wakagi T. ; Fushinobu, S.
  • Journal Title: Bioscience, Biotechnology, and Biochemistry 2012 Volume: 76 Pages: 423-428
  • Peer Reviewed
• [Journal Article] Crystal Structures of Glycoside Hydrolase Family 51 α-L-Arabinofuranosidase from Thermotoga maritima (2012)
  • Author(s): Do-Hyun Im, Kei-ichi Kimura, Fumitaka Hayasaka, Tomonari Tanaka, Masato Noguchi, Atsushi Kobayashi, Shin-ichiro Shoda, Kentaro Miyazaki, Takayoshi Wakagi, Shinya Fushinobu
  • Journal Title: Bioscience, Biotechnology, and Biochemistry Volume: 76 Issue: 2 Pages: 423-428
  • DOI: 10.1271/bbb.110902
  • NAID: 10030400456
  • ISSN: 0916-8451, 1347-6947
  • Peer Reviewed
• [Journal Article] Direct dehydrative pyridylthio-glycosidation of unprotected sugars in aqueous media using 2-Chloro-1, 3-dimethylimidazolinium chloride as a condensing agent. (2011)
  • Author(s): Yoshida, N. ; Noguchi, M. ; Tanaka, T. ; Matsumoto, T. ; Aida, N. ; Ishihara, M. ; Kobayashi, A. ; Shoda, S.
  • Journal Title: Chemistry an Asian Journal 2011 Volume: 6,(7) Pages: 1876-1885
  • Peer Reviewed
• [Journal Article] Direct Dehydrative Pyridylthio-Glycosidation of Unprotected Sugars in Aqueous Media Using 2-Chloro-1,3-dimethylimidazolinium Chloride as a Condensing Agent (2011)
  • Author(s): Naoki Yoshida, Masato Noguchi, Tomonari Tanaka, Takeshi Matsumoto, Naoya Aida, Masaki Ishihara, Atsushi Kobayashi, Shin-ichiro Shoda
  • Journal Title: Chemistry Asian Journal Volume: 6 Issue: 7 Pages: 1876-1885
  • DOI: 10.1002/asia.201000896
  • Peer Reviewed
• [Journal Article] Novel dialkoxytriazine-type glycosyl donors for cellulase-catalysed lactosylation. (2010)
  • Author(s): Tanaka, T. ; Noguchi, M. ; Watanabe, K. ; Misawa, T. ; Ishihara, M. ; Kobayashi, A. ; Shoda, S.
  • Journal Title: Organic & Biomolecular Chemistry 2010 Volume: 8 (22) Pages: 5126-5132
  • Peer Reviewed
• [Journal Article] 4, 6-Dimethoxy-1, 3, 5-triazine oligoxyloglucans : Novel one-step preparable substrates for studying action of endo-beta-1, 4-glucanase III from Trichoderma reesei. (2010)
  • Author(s): Kobayashi, A. ; Tanaka, T. ; Watanabe, K. ; Ishihara, M. ; Noguchi, M. ; Okada, H. ; Morikawa, Y. ; Shoda, S.
  • Journal Title: Bioorganic & Medicinal Chemistry Letters 2010 Volume: 20 (12) Pages: 3588-3591
  • 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 oxazoline. (2010)
  • Author(s): Umekawa, M. ; Higashiyama, T. ; Koga, Y. ; Tanaka, T. ; Noguchi, M. ; Kobayashi, A. ; Shoda, S. ; Huang, W. ; Wang, L. X. ; Ashida, H. ; Yamamoto, K.
  • Journal Title: Biochimica Et Biophysica Acta-General Subjects 2010 Volume: 1800 (11) Pages: 1203-1209
  • NAID: 120002647341
  • 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-β-1, 4-glucanase. (2010)
  • Author(s): Tanaka, T. ; Noguchi, M. ; Ishihara, M. ; Kobayashi, A. ; Shoda, S.-i.
  • Journal Title: Macromolecular Symposia 2010 Volume: 297 (1) 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-β-1,4-glucanase III from Trichoderma reesei (2010)
  • Author(s): Atsushi Kobayashi, Tomonari Tanaka, Kazuhito Watanabe, Masaki Ishihara, Masato Noguchi, Hirofumi Okada, Yasushi Morikawa, Shin-ichiro Shoda
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 20 Pages: 3588-3591
  • Peer Reviewed
• [Journal Article] Efficient transfer of sialo-oligosacchadde onto proteins by combined use of a glycosynthase-like mutant of Mucor hiemalis endoglycosidase and synthetic sialo-complex-type sugar oxazoline (2010)
  • Author(s): Midori Umekawa, Takayuki Higashiyama, Yurie Koga, Tomonari Tanaka, Masato Noguchi, Atsushi Kobayashi, Shin-ichiro Shoda, Wei Huang, Lai-Xi Wang, Hisashi Ashida, Kenji Yamamoto
  • Journal Title: Biochimica et Biophysica Acta Volume: 1800 Pages: 1203-1209
  • Peer Reviewed
• [Journal Article] Novel dialkoxytriazine-type glycosyl donors for cellulase-catalysed lactosylation (2010)
  • Author(s): Tomonari Tanaka, Masato Noguchi, Kazuhito Watanabe, Takuya Misawa, Masaki Ishihara, Atsushi Kobayashi, Shin-ichiro Shoda
  • Journal Title: Organic & Biomolecular Chemistry Volume: 8 Pages: 5126-5132
  • Peer Reviewed
• [Journal Article] Dimethoxy Triazine Glycosides as New Glycosyl Donors for Chemo-enzymatic Synthesis of Oligosaccharides. (2009)
  • Author(s): Tanaka, T. ; Kobayashi, A. ; Noguchi, M. ; Kimura, K. ; Watanabe, K. ; Shoda, S.
  • Journal Title: Journal of Applied Glycoscience 2009 Volume: 56 Pages: 83-88
  • NAID: 10025408944
  • Peer Reviewed
• [Journal Article] Direct Transformation of Unprotected Sugars to Aryl 1-Thio-beta-glycosides in Aqueous Media Using 2-Chloro-1, 3-dimethylimidazolinium Chloride. (2009)
  • Author(s): Tanaka, T. ; Matsumoto, T. ; Noguchi, M. ; Kobayashi, A. ; Shoda, S.
  • Journal Title: Chemistry Letters 2009 Volume: 38 (5) Pages: 458-459
  • Peer Reviewed
• [Journal Article] One-step conversion of unprotected sugars to beta-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution. (2009)
  • Author(s): Tanaka, T. ; Nagai, H. ; Noguchi, M. ; Kobayashi, A. ; Shoda, S.
  • Journal Title: Chemical Communications 2009 Volume: 23 Pages: 3378-3379
  • Peer Reviewed
• [Journal Article] Direct Transformation of Unprotected Sugars to Aryl 1-Thio-β-glycosides in Aqueous Media Using 2-Chloro-1,3-dimethylimidazolinium Chloride (2009)
  • Author(s): Tomonari Tanaka, Takeshi Matsumoto, Masato Noguchi, Atsushi Kobayashi, Shin-ichiro Shoda
  • Journal Title: Chemistry Letters 38 Pages: 458-459
  • NAID: 10025121899
  • Peer Reviewed
• [Journal Article] One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution (2009)
  • Author(s): Tomonari Tanaka, Hikaru Nagai, Masato Noguchi, Atsushi Kobayashi, Shin-ichiro Shoda
  • Journal Title: Chemical Commnunications 2009 Pages: 3378-3379
  • Peer Reviewed
• [Presentation] 新規脱水縮合剤による水溶液中での糖オキサゾリン誘導体の一段階合成 (2012)
  • Author(s): 野口真人
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2012-03-27
• [Presentation] 一段階で調製可能なキシロビオースモノマーの酵素的重縮合 (2011)
  • Author(s): 野口真人
  • Organizer: 第60回高分子学会年次大会
  • Place of Presentation: 大阪
  • Year and Date: 2011-05-27
• [Presentation] DMT誘導体の酵素的.-N-アセチルグルコサミニル化反応によるピロリ菌増殖抑制オリゴ糖の合成 (2011)
  • Author(s): 野口真人
  • Organizer: 日本化学会第91春季年会
  • Year and Date: 2011-03-11
• [Presentation] DMT誘導体の酵素的α-N-アセチルグルコサミニル化反応によるピロリ菌増殖抑制オリゴ糖の合成 (2011)
  • Author(s): 野口真人
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 日本化学会第91春季年会(2011)講演予稿集
  • Year and Date: 2011-03-11
• [Presentation] 水溶性脱水縮合剤を用いる遊離糖鎖からの多糖合成 (2010)
  • Author(s): 野口真人
  • Organizer: 化学系学協会東北大会
  • Place of Presentation: 盛岡
  • Year and Date: 2010-09-25
• [Presentation] Practical Synthesis of Sugar Oxazoline Derivative in Water (2010)
  • Author(s): M. Noguchi
  • Organizer: 25th International Carbohydrate Symposium
  • Place of Presentation: 幕張
  • Year and Date: 2010-08-03
• [Presentation] オキサゾリン誘導体の直接合成を利用した遊離糖からの多糖合成 (2010)
  • Author(s): 野口真人
  • Organizer: 第59回高分子学会年次大会
  • Place of Presentation: 横浜
  • Year and Date: 2010-05-26
• [Presentation] オキサゾリン誘導体の直接合成を活用した遊離糖からのワンポット配糖化反応 (2010)
  • Author(s): 野口真人
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 東大阪
  • Year and Date: 2010-03-28
• [Presentation] オキサゾリン誘導体の直接合成を活用 した遊離糖からのワンポット配糖化反応 (2010)
  • Author(s): 野口真人
  • Organizer: 日本化学会第90回春季年会
  • Place of Presentation: 東大阪
  • Year and Date: 2010-03-28
• [Presentation] 脱水縮合剤を利用した水溶液中でのチオグリコシドの一段階合成 (2009)
  • Author(s): 野口真人
  • Organizer: 第58回日本応用糖質科学会平成21年度大会
  • Place of Presentation: 弘前
  • Year and Date: 2009-09-16
• [Presentation] 水溶液中における還元末端アノマー位の直接活性化と誘導化 (2009)
  • Author(s): 野口真人
  • Organizer: 第29回日本糖質学会年会
  • Place of Presentation: 高山
  • Year and Date: 2009-09-11
• [Presentation] 水溶液中における還元末端アノマー位の直接活性化と誘導化 (2009)
  • Author(s): 野口真人
  • Organizer: 第29回 日本糖質学会年会
  • Place of Presentation: 高山
  • Year and Date: 2009-09-11
• [Presentation] Direct Synthesis of Sugar Oxazoline Derivatives in Water (2009)
  • Author(s): M. Noguchi
  • Organizer: 15th European Carbohydrate Symposium
  • Place of Presentation: ウィーン
  • Year and Date: 2009-07-23
• [Presentation] DIRECT SYNTHESIS OF SUGAR OXAZOLINE DERIVATIVES IN WATER (2009)
  • Author(s): 野口真人
  • Organizer: 15th European Carbohydrate Symposium
  • Place of Presentation: ウィーン, オーストリア
  • Year and Date: 2009-07-23
• [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, 野口真人
  • Publisher: CMC出版
• [Book] バイオ医薬品開発における糖鎖技術, 第9章オキサゾリン基質中間体と糖タンパク質医薬品 (2010)
  • Author(s): 正田晋一郎, 野口真人
  • Publisher: CMC出版