Design of enzymatic glycosylation reaction system toward unrecognized substrates such as macromolecules and interface.

• Project/Area Number: 19750086
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Polymer chemistry
• Research Institution: Tohoku University
• Principal Investigator: KOBAYASHI Atsushi Tohoku University, 大学院・工学研究科, 助教 (90361138)
• Project Period (FY): 2007 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥2,820,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥420,000); Fiscal Year 2009: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2008: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2007: ¥1,000,000 (Direct Cost: ¥1,000,000)
• Keywords: 糖鎖高分子 / 酵素触媒高分子反応 / アマドリ転位反応 / 酵素触媒反応 / 糖脂質 / 糖鎖修飾界面 / 包接錯体

Research Abstract

It is very important to develop the addition reaction onto macromolecules and interfaces by enzymes, although these substrates are difficult to be accepted by the enzymes. In this research, I successfully developed the improved enzymatic glycosylation reaction system by the simple chemical treatment of these substrates.

Research Products

• [Journal Article] Efficient Synthesis of Sugar Oxazolines from Unprotected N-Acetyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water. (2009)
  • Author(s): Noguchi, M., Tanaka, T., Gyakushi, H., Kobayashi, A., Shoda, S.
  • Journal Title: J.Org.Chem. 74 Pages: 2210-2212
  • Peer Reviewed
• [Journal Article] One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution (2009)
  • Author(s): Tanaka, T., Nagai, H., Noguchi, M., Kobayashi, A., Shoda, S.
  • Journal Title: Chem.Commun. 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): Tanaka, T., Matsumoto, T., Noguchi, M., Kobayashi, A., Shoda, S.
  • Journal Title: Chem.Lett. 38 Pages: 458-459
  • NAID: 10025121899
  • 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: J.Appl.Glycosci. 56 Pages: 83-88
  • NAID: 10025408944
  • Peer Reviewed
• [Journal Article] Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride (2009)
  • Author(s): Tanaka, T., Huang, W., Noguchi, M., Kobayashi, A., Shoda, S.
  • Journal Title: Tetrahedron Lett. 50 Pages: 2154-2157
  • Peer Reviewed
• [Journal Article] Synthesis of artificial oligosaccharides by polycondensation of 2'-O-methyl cellobiosyl fluoride and mannosyl fluoride catalyzed by cellulase, in :J.Kadokawa (Ed.), Interfacial Researches in Fundamental and Material Sciences of Oligo-and Polysaccharides (2009)
  • Author(s): R.Izumi, Y.Suzuki, Y.Shimizu, M.Fujita, M.Ishihara, M.Noguchi, A.Kobayashi, S.Shoda
  • Journal Title: Transworld Research Network, Kerala Pages: 45-68
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of Sugar Oxazolines from Unprotected N-Acetyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water. (2009)
  • Author(s): Noguchi, M., Tanaka, T., Gyakushi, H., Kobayashi, A., Shoda, S.
  • Journal Title: J. Org. Chem. 74 Pages: 2210-2212
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of Sugar Oxazolines from Unprotected N-Acetyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water (2009)
  • Author(s): Noguchi, M., Tanaka, T., Gyakushi, H., Kobayashi, A., Shoda, S.
  • Journal Title: Journal of Organic Chemistry 74 Pages: 2210-2212
  • Peer Reviewed
• [Journal Article] Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride (2009)
  • Author(s): Tanaka, T., Huang, W.C., Noguchi, M., Kobayashi, A., Shoda, S.
  • Journal Title: Tetrahedron Letters 50 Pages: 2154-2157
  • Peer Reviewed
• [Journal Article] One-step conversion of unprotected sugars to β-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 Pages: 3378-3379
  • 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 38 Pages: 458-459
  • 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.-i., Watanabe, K., Shoda, S.-i.
  • Journal Title: Journal of Applied Glycoscience 56 Pages: 83-88
  • NAID: 10025408944
• [Journal Article] Efficient Synthesis of Sugar Oxazolines from Unprotected N-Acetyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water (2009)
  • Author(s): M. Noguchi, T. Tanaka, H. Gyaku shi, A. Kobayashi, S. I. Shoda
  • Journal Title: J. Org. Chem 74 Pages: 2010-2012
  • Peer Reviewed
• [Journal Article] Direct synthesis of 1, 6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1, 3-dimethylimidazolinium chloride (2009)
  • Author(s): T. Tanaka, W. C. Huang, M. Nog uchi, A. Kobayashi, S. Shoda
  • Journal Title: Tetrahedr. Lett (in press)
  • Peer Reviewed
• [Journal Article] A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis : 4,6-dimethoxy-1,3,5-triazin-2-yl glycoside. (2008)
  • Author(s): Tanaka, T., Noguchi, M., Kobayashi, A., Shoda, S.
  • Journal Title: Chem.Commun. Pages: 2016-2018
  • Peer Reviewed
• [Journal Article] A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis: 4, 6-dimethoxy-1, 3, 5-triazin-2-yl glycoside. (2008)
  • Author(s): Tanaka, T., Noguchi, M., Kobayashi, A., Shoda, S.
  • Journal Title: Chem. Commun.
  • Peer Reviewed
• [Journal Article] A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis : 4, 6-Dimethoxy-1, 3, 5-triazin-2-y1 glycoside (2008)
  • Author(s): T. Tanaka, W. C. Huang, M. Nog uchi, A. Kobayashi, S. Shoda
  • Journal Title: Chem. Commun Pages: 2016-2018
  • Peer Reviewed
• [Journal Article] Colorimetric assay for evaluating glycosyl fluoride-hydrolyzing activity of glycosidase by using alizarin complexon reagent. (2007)
  • Author(s): S. Shoda, K. Shintate, M. Ishihara, M. Noguchi, A. Kobayashi
  • Journal Title: Chem. Lett. 36 Pages: 16-17
  • NAID: 10018662406
  • Peer Reviewed
• [Journal Article] Design and utilization of chitinases with low hydrolytic activities. (2007)
  • Author(s): M. Kohri, A. Kobayashi, S. Shoda
  • Journal Title: Trends Glycosci. Glycotechnol. 19 Pages: 165-180
  • NAID: 10019855941
  • Peer Reviewed
• [Journal Article] Spectrophotometric assay by using glycosyl fluorides. (2007)
  • Author(s): M. Ishihara, A. Kobayashi, M. Noguchi, S.-i. Shoda
  • Journal Title: Cellulose Communications 14 Pages: 58-61
  • NAID: 40015564547
• [Journal Article] Design and utilization of chitinases with low hydrolytic activities. (2007)
  • Author(s): A. Kobayashi, M. Kohri, S. Shoda
  • Journal Title: Mirai Zairyo 7 Pages: 45-53
  • NAID: 10019855941
• [Presentation] A new route to labeled oligosaccharides via glycosyl azides in aqueous media. (2009)
  • Author(s): Kobayashi, A., Nagai, H., Tanaka, T., Noguchi, M., Ishihara, M., Shoda, S.
  • Organizer: 20th International Symposium on Glycoconjugates.
  • Place of Presentation: Puerto Rico, USA
  • Year and Date: 2009-12-03
• [Presentation] 無保護キトオリゴ糖からの一段階糖オキサゾリン化反応を活用する酵素触媒キチン合成 (2009)
  • Author(s): 石倉久美子、田中知成、野口真人、小林厚志、正田晋一郎、渡邉剛志
  • Organizer: 平成21年度日本応用糖質科学会大会
  • Place of Presentation: 弘前大学、弘前市
  • Year and Date: 2009-09-15
• [Presentation] DMT-α-D-N-アセチルグルコサミニドを基質としたときのα-D-N-アセチルグルコサミニダーゼの触媒作用 (2009)
  • Author(s): 中村美和、田中知成、野口真人、小林厚志、正田晋一郎、藤田雅也、土田明子、水野真盛
  • Organizer: 平成21年度日本応用糖質科学会大会
  • Place of Presentation: 弘前大学、弘前市
  • Year and Date: 2009-09-15
• [Presentation] DMT-β-D-グルコサミニドを基質としたときのキトサナーゼの触媒反応 (2009)
  • Author(s): 和田有功、田中知成、野口真人、小林厚志、正田晋一郎、深溝慶
  • Organizer: 平成21年度日本応用糖質科学会大会
  • Place of Presentation: 弘前大学、弘前市
  • Year and Date: 2009-09-15
• [Presentation] 新しい糖鎖ラベル化法 (2009)
  • Author(s): 小林厚志、永井光、田中知成、野口真人、正田晋一郎
  • Organizer: 平成21年度日本応用糖質科学会大会
  • Place of Presentation: 弘前大学、弘前市
  • Year and Date: 2009-09-15
• [Presentation] DMT-β-D-ガラクトシドを基質としたときのβ-ガラクトシダーゼによる糖転移反応 (2009)
  • Author(s): 田中知成、木村敬一、野口真人、小林厚志、正田晋一郎
  • Organizer: 平成21年度日本応用糖質科学会大会
  • Place of Presentation: 弘前大学、弘前市
  • Year and Date: 2009-09-15
• [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、松本健、田中知成、小林厚志、正田晋一郎
  • Organizer: 平成21年度日本応用糖質科学会大会
  • Place of Presentation: 弘前大学、弘前市
  • Year and Date: 2009-09-15
• [Presentation] 糖の特性を活用する有用糖質の酵素合成 (2009)
  • Author(s): 小林厚志
  • Organizer: 日本応用糖質科学会東北支部山形地区講演会
  • Place of Presentation: 山形テルサ、山形市
  • Year and Date: 2009-07-03
• [Presentation] 保護基を用いないグリコシルアジドの一段階合成 (2009)
  • Author(s): 田中知成、黄偉峻、野口真人、小林厚志、正田晋一郎
  • Organizer: 第20回万有仙台シンポジウム
  • Place of Presentation: 仙台国際センター、仙台
  • Year and Date: 2009-06-13
• [Presentation] 酵素-化学法によるタンパク質への糖鎖導入技術の開発 (2009)
  • Author(s): 小林厚志・相沢健太・野口真人・正田晋一郎
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学船橋キャンパス
  • Year and Date: 2009-03-29
• [Presentation] 水溶液における無保護セロオリゴ糖の一段階アンヒドロ化反応 (2009)
  • Author(s): 黄偉峻、田中知成、野口真人、小林厚志、正田晋一郎
  • Organizer: セルロース学会第16回年次大会
  • Place of Presentation: 北海道大学、札幌市
• [Presentation] 糖タンパク質のテーラーメード合成法 (2008)
  • Author(s): 相沢健太・小林厚志・野口真人・正田晋一郎
  • Organizer: 化学系9学協会東北地方大会
  • Place of Presentation: 人戸工業大学
  • Year and Date: 2008-10-12
• [Presentation] 多糖の特性を活用する酵素触媒糖転移反応の効率化 (2008)
  • Author(s): 小林厚志, 伊藤博, 野口真人, 正田晋一郎
  • Organizer: 日本生物工学会
  • Place of Presentation: 東北学院大学土樋キャンパス
  • Year and Date: 2008-08-29
• [Presentation] Enzymatic synthesis of glyco-surfactant via ultrasound irradiation onto substrate mixture containing polysaccharide and glycosyl acceptor (2008)
  • Author(s): Kobayashi, A., Yamamoto、K., Itoh, H., Noguchi, M., Shoda, S.
  • Organizer: 24th International Carbohydrate Symposium Oslo
  • Place of Presentation: Norway
  • Year and Date: 2008-07-29
• [Presentation] Enzymatic Synthesis of Glyco-surfactant via Ultrasound Irradiation onto Substrate Mixture Containing Polysaccharide and Glycosyl Acceptor (2008)
  • Author(s): A. Kobayashi, K. Yamamoto, H. Ito, M. Noguchi, S. Shoda
  • Organizer: International Carbohydrate Symposium
  • Place of Presentation: International Carbohydrate Symposium
  • Year and Date: 2008-07-28
• [Presentation] アマドリ転位および酵素的配糖化を利用する新規糖タンパク質の合成. (2008)
  • Author(s): 小林厚志, 小山内博紀, 野口真人, 正田晋一郎
  • Organizer: 日本農芸化学会大会
  • Place of Presentation: 名城大学
  • Year and Date: 2008-03-28
• [Presentation] α-アミラーゼ糖転移の結合様式に与えるアグリコン構造の影響. (2007)
  • Author(s): 山本憲司, 小林厚志, 石原正規, 野口真人, 伊藤博, 正田晋一郎, 殿塚隆史, 坂野好幸
  • Organizer: 日本農芸化学会東北支部大会
  • Place of Presentation: 東北大学農学部
  • Year and Date: 2007-11-10
• [Presentation] アマドリ転位を利用する非糖タンパク質へのN-結合型糖鎖の導入. (2007)
  • Author(s): 小山内博紀, 野口真人, 小林厚志, 正田晋一郎
  • Organizer: 高分子討論会
  • Place of Presentation: 名古屋工業大学
  • Year and Date: 2007-09-19
• [Presentation] Chemo-enzymatic synthesis of glycoprotein from Hen Egg lysozyme via the Amadori rearrangement (2007)
  • Author(s): Kobayashi, A., Osanai, H, Murakami, T, Noguchi, M., Shoda, S.
  • Organizer: 19th International Symposium on Glycoconjugates Cairns
  • Place of Presentation: Australia
  • Year and Date: 2007-07-17
• [Presentation] Chemo-enzymatic synthesis of glycoprotein from Hen Egg lysozyme via the Amadori rearrangement (2007)
  • Author(s): Kobayashi, A., Osanai, H, Murakami, T, Noguchi, M., Shoda, S.
  • Organizer: 19 th International Symposium on Glycoconjugates Cairns
  • Place of Presentation: Australia
  • Year and Date: 2007-07-17
• [Presentation] アグリコンの構造によるα-アミラーゼの糖転移産物の結合制御 (2007)
  • Author(s): 山本憲司, 小林厚志, 石原正規, 野口真人, 伊藤博, 正田晋一郎, 殿塚隆史, 坂野好幸
  • Organizer: 高分子学会
  • Place of Presentation: 京都国際会議場
  • Year and Date: 2007-05-31
• [Book] 「酵素的グリコシル化に用いる糖供与体の一段階合成技術」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
  • Publisher: シーエムシー出版
• [Book] 複合糖質の化学と最新応用技術(酵素的グリコシル化に用いる糖供与体の一段階合成技術) (2009)
  • Author(s): 野口真人、田中知成、小林厚志、正田晋一郎
  • Publisher: シーエムシー出版
• [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
  • 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): 野口真人、小林厚志、正田晋一郎
  • Total Pages: 6
  • Publisher: シーエムシー出版
• [Remarks] 2008年度日本農芸化学会東北支部奨励賞受賞「糖質加水分解酵素を駆使する配糖化基盤技術の開発」
• [Remarks] 2008年度日本農芸化学会東北支部奨励賞受賞「糖質加水分解酵素を駆使する配糖化基盤技術の開発」
• [Patent(Industrial Property Rights)] 配糖体およびその製造方法 (2008)
  • Inventor(s): 正田晋一郎、小林厚志、野口真人、田中知成、永井光、松本健
  • Industrial Property Rights Holder: 東北大学
  • Industrial Property Number: 2008-150123
  • Filing Date: 2008-06-09
• [Patent(Industrial Property Rights)] 層己糖体及びその製造方法 (2008)
  • Inventor(s): 正田晋一郎、小林厚志、野口真人、田中知成、永井光、松本健
  • Industrial Property Rights Holder: 東北大学
  • Filing Date: 2008-06-09
• [Patent(Industrial Property Rights)] アンヒドロ糖及びその製造方法 (2007)
  • Inventor(s): 正田晋一郎、小林厚志、野口真人、田中知成
  • Industrial Property Rights Holder: 東北大学
  • Industrial Property Number: 2007-254281
  • Filing Date: 2007-09-28