Synthesis of Polysaccharides by Dehydrative Condensation in Water

• Project/Area Number: 23655094
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Polymer chemistry
• Research Institution: Tohoku University
• Principal Investigator: SHODA Shin-ichiro 東北大学, 大学院・工学研究科, 教授 (10143364)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 高分子合成 / 多糖 / 重縮合 / キシラン / キトオリゴ糖 / セルラーゼ / キチナーゼ / 脱水縮合剤 / 糖オキサゾリン / 変異型キチナーゼ / ＤＭＣ / 糖転移反応 / αーＮ－アセチルグルコサミニド / ピロリ菌抑制作用 / キトヘプタオース

Research Abstract

A novel monomer, 4,6-dimethoxy 1,3,5-triazin 2-yl xylobioside, was directly synthesized from xylobiose in water. Enzymatic polycondensation of the resulting monomer proceeded by using cellulase preparation or partially purified xylanase as an enzyme.

Research Products

• [Journal Article] Direct Introduction of Detachable Fluorescent Tag into Oligosaccharides (2013)
  • 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
  • Peer Reviewed
• [Journal Article] Facile Synthesis of Oligosaccharide-Poly(L-Lactide) Conjugates Forming Nanoparticles with Saccharide Core and Shell (2013)
  • Author(s): T. Tanaka, H. Fukuhara, S. Shoda, Y.Kimura
  • Journal Title: Chem. Lett Volume: 42 Pages: 197-199
  • Peer Reviewed
• [Journal Article] オリゴ糖還元末端の蛍光ラベル化 (2013)
  • Author(s): 吉田尚生,正田晋一郎
  • Journal Title: Cellulose Commun Volume: 20 Pages: 20-24
• [Journal Article] A Practical One-Step Synthesis of 1,2-Oxazoline Derivatives from Unprotected Sugars and Its Application to Chemoenzymaticβ-N-Acetylglucosaminidation of Disalo-oligosaccharide (2012)
  • Author(s): M. Nougchi, T. Fujieda, W. C. Huang, M.Ishihara, A. Kobayashi, S. Shoda
  • Journal Title: Helv. Chim. Acta Volume: 95 Pages: 1928-1936
  • Peer Reviewed
• [Journal Article] One-pot chemo-enzymatic route to chitoheptaose via specific transglycosylation of chitopentaose-oxazoline on chitinase-template (2012)
  • 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
  • Peer Reviewed
• [Journal Article] A dimethoxytriazine type glycosyl donor enables facile chemo-enzymatic route toward .-linked N-acetylglucosaminyl galactose disaccharide unit from gastric mucin (2012)
  • 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: 48 Pages: 5560-5562
  • 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] α-N-Acetylgalactosaminidase from Infant-associated Bifidobacteria Belonging to Novel Glycoside Hydrolase Family 129 is Implicated in Alternative Mucin Degradation Pathway (2012)
  • 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] A dimethoxytriazine type glycosyl donor enables facile chemo-enzymatic route towardα-linked N-acetylglucosaminyl-galactose disaccharide unit from gastric mucin (2012)
  • 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
  • Peer Reviewed
• [Journal Article] A Practical One-Step Synthesis of 1,2-Oxazoline Derivatives from Unprotected Sugars and Its Application to Chemoenzymatic -N-Acetylglucosaminidation of Disialo-oligosaccharide (2012)
  • Author(s): M. Noguchi
  • Journal Title: Helvetica Chimica Acta Volume: 95 Pages: 1928-1936
  • 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 orientalis (2011)
  • 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
  • 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
• [Presentation] 糖オキサゾリンを糖供与体とするLacto-N-tetraoseの酵素合成 (2013)
  • Author(s): 小林厚志,瀬野宗,黄偉峻,野口真人,片山高嶺,正田晋一郎
  • Organizer: 日本農芸化学会
  • Place of Presentation: 仙台
  • Year and Date: 2013-03-26
• [Presentation] アマドリ転位反応を経由する化学‐酵素法により生成した人工糖タンパク質の解析 (2013)
  • Author(s): 吉田尚生,酒井謙介,小林厚志,正田晋一郎
  • Organizer: 日本農芸化学会
  • Place of Presentation: 仙台
  • Year and Date: 2013-03-26
• [Presentation] In situで発生するルイス酸により促進されるグリコシル化 (2013)
  • Author(s): 斎藤幸恵,高木優香,野口真人,正田晋一郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津
  • Year and Date: 2013-03-23
• [Presentation] アミノ糖の一段階活性化を用いるグリコシル化 (2013)
  • Author(s): 野口真人,梶友祐,正田晋一郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津
  • Year and Date: 2013-03-23
• [Presentation] 水中におけるα‐フッ化糖の一段階合成 (2013)
  • Author(s): 中谷健一,野口真人,正田晋一郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津
  • Year and Date: 2013-03-23
• [Presentation] アノマー位を先に活性化する新規配糖化プロセス (2013)
  • Author(s): 佐藤希美,石原正規,野口真人,正田晋一郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津
  • Year and Date: 2013-03-23
• [Presentation] 保護基を使用しないオリゴ糖の配糖化 (2012)
  • Author(s): 正田晋一郎,高木優香,斎藤幸恵,石原正規,野口真人
  • Organizer: 日本応用糖質科学会平成24年度大会
  • Place of Presentation: 府中
  • Year and Date: 2012-09-19
• [Presentation] バクテロイデス菌由来α‐N-Acetylglucosaminidaseへの糖鎖結合モジュール(CBM)付与効果 (2012)
  • Author(s): 土田明子,藤田雅也,森昌子,後藤浩太朗,弘瀬友里子,大隅賢二,野口真人,正田晋一郎,芦田久,水野真盛
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島
  • Year and Date: 2012-09-19
• [Presentation] 糖オキサゾリン誘導体の一段階合成を活用したワンポット配糖化反応 (2012)
  • Author(s): 野口真人,藤枝司,小林厚志,正田晋一郎
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島
  • Year and Date: 2012-09-17
• [Presentation] Synthesis of Oligosaccharide-based Glycolipids under Hydrogenolytic Conditions (2012)
  • Author(s): 李格非,野口真人,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-16
• [Presentation] アジ化糖を用いた固体表面の修飾 (2012)
  • Author(s): 大築貴洋,野口真人,小林厚志,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-16
• [Presentation] (2012)
  • Author(s): 斎藤幸恵,高木優香,野口真人,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-16
• [Presentation] マイクロリアクターを利用した糖オキサゾリン誘導体の合成 (2012)
  • Author(s): 酒井謙介,吉田尚生,小林厚志,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-16
• [Presentation] シリル保護された糖トリアジン誘導体を供与体とする配糖体合成 (2012)
  • Author(s): 佐藤希美,野口真人,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-15
• [Presentation] 水溶媒中での無保護糖の一段階フッ素化 (2012)
  • Author(s): 中谷健一,野口真人,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-15
• [Presentation] 酵素的重縮合による人工キシランの合成 (2012)
  • Author(s): 山口祐太,野口真人,小林厚志,正田晋一郎
  • Organizer: 平成24年度化学系学協会東北大会
  • Place of Presentation: 秋田
  • Year and Date: 2012-09-15
• [Presentation] Protection-free glycosylation of oligosaccharides (2012)
  • Author(s): S. Shoda
  • Organizer: European-Japanese Workshop on Cellulose and Functionl Polysaccharides 2012
  • Place of Presentation: 東京
  • Invited
• [Presentation] Protection-Free Glycosylation (2011)
  • Author(s): S. Shoda
  • Organizer: Asian Communications of Glycobiology and Glycotechnology(招待講演)
  • Place of Presentation: Shanghai (China)
• [Book] 糖化学者の挑戦‐分子量のそろった糖タンパク質をつくる‐,化学,67 (2012)
  • Author(s): 野口真人,正田晋一郎
  • Publisher: 化学同人
• [Book] 化学 (2012)
  • Author(s): 野口真人
  • Total Pages: 2
  • Publisher: 化学同人
• [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: シーエムシー出版
• [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: シーエムシー出版
• [Remarks]
  • URL: http://www.che.tohoku.ac.jp/~poly/
• [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: 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 (2011)
  • Inventor(s): 藤田雅也、土田明子、正田晋一郎、田中知成
  • Industrial Property Rights Holder: 藤田雅也、土田明子、正田晋一郎、田中知成
  • Industrial Property Number: 2011-190079
  • Filing Date: 2011