Facile Synthesis of Glycoconjugate based on Direct Synthesis of Glycosyl Azide in Water

• Project/Area Number: 22850010
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Kyoto Institute of Technology
• Principal Investigator: TANAKA Tomonari 京都工芸繊維大学, 工芸科学研究科, 助教 (70585695)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2011: ¥1,495,000 (Direct Cost: ¥1,150,000、Indirect Cost: ¥345,000); Fiscal Year 2010: ¥1,625,000 (Direct Cost: ¥1,250,000、Indirect Cost: ¥375,000)
• Keywords: 糖鎖高分子 / オリゴ糖 / クリックケミストリー / 無保護 / 脱水縮合剤 / 直接活性化

Research Abstract

It is very difficult to prepare glycoconjugates with oligosaccharide by chemical synthesis because it necessitates laborious tasks including protection and deprotection of hydroxy groups. Then, the facile method of glycoconjugates with oligosaccharide is demanded. In this research, I successfully developed the protecting-group-free addition of oligosaccharide by direct azidation of unprotected sugar and Click chemistry starting from unprotected sugar.

Research Products

• [Journal Article] A dimethoxytriazine type glycosyl donor enables a 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, Shin-ichiro Shoda
  • Journal Title: Chem. Commun Volume: 48 Pages: 5560-5562
  • Peer Reviewed
• [Journal Article] Anτ-N-Acetylgalactosaminidase from Infant-associated Bifid bacteria Belonging to a Novel Glycoside Hydrolase Family 129 is Implicated in an Alternative Mucin Degradation Pathway (2012)
  • Author(s): Masashi Kiyohara, Takashi Nakatomi, Shin Kurihara, Shinya Fushinobu, Hideyuki Suzuki, Tomonari Tanaka, Shin-ichiro Shoda, Takane Katayama, Kenji Yamamoto, Hisashi Ashida
  • Journal Title: J. Biol. Chem Volume: 287 Issue: 1 Pages: 693-700
  • DOI: 10.1074/jbc.m111.277384
  • 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] An α-N-Acetylgalactosaminidase from Infant-associated Bifidobacteria Belonging to a Novel Glycoside Hydrolase Family 129 is Implicated in an Alternative Mucin Degradation Pathway (2012)
  • Author(s): M.Kiyohara, T.Nakatomi, S.Kurihara, S.Fushinobu, H.Suzuki, T.Tanaka, S.Shoda, T.Katayama, K.Yamamoto, H.Ashida
  • Journal Title: Journal of Biological Chemistry 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 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] 簡便な糖鎖合成を目指して-保護基を使わない糖誘導体の直截的水Scheme 3クリックケミストリーによる糖修飾ポリ乳酸の合成.中合成- (2011)
  • Author(s): 田中知成
  • Journal Title: 繊維学会誌(繊維と工業) Volume: 67 Pages: 322-324
  • URL: https://www.jstage.jst.go.jp/browse/fiber/67/11/_contents/-char/ja/
  • Peer Reviewed
• [Journal Article] 簡便な糖鎖合成を目指して-保護基を使わない糖誘導体の直截的水中合成- (2011)
  • Author(s): 田中知成
  • Journal Title: 繊維学会誌繊維と工業 Volume: 67 Pages: 322-324
  • NAID: 10030181018
• [Journal Article] 4, 6-Dimethoxy-1, 3, 5-triazin-2-ylυ-D-glycosaminides : Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-υ-D-glucosaminidase from Amycolatopsis orientalis
  • Author(s): Tomonari Tanaka, Tomonori Wada, Masato Noguchi, Masaki Ishihara, Atsushi Kobayashi, Takayuki Ohnuma, Tamo Fukamizo, Ryszard Brzezinski, Shin-ichiro Shoda
  • Journal Title: J. Carbohydr. Chem Volume: (in press)
  • Peer Reviewed
• [Presentation] Protecting-group-free Synthesis of Saccharide-terminated Polylactides by Direct Azidation of Unprotected Sugar and Click Chemistry (2012)
  • Author(s): Tomonari Tanaka, Hiroyuki Fukuhara, Yoshiharu Kimura
  • Organizer: 26th International Carbohydrate Symposium
  • Place of Presentation: Madrid, Spain
  • Year and Date: 2012-07-23
• [Presentation] Protecting-group-free Synthesis of Saccharide-terminated Polylactides by Direct Azidation of Unprotected Sugar and Click Chemistry (2012)
  • Author(s): T.Tanaka, H.Fukuhara, Y.Kimura
  • Organizer: 26th International Carbohydrate Symposium
  • Place of Presentation: Madrid (Spain)(発表確定)
  • Year and Date: 2012-07-23
• [Presentation] 糖修飾ポリ乳酸の保護基フリー合成と会合挙動解析 (2012)
  • Author(s): 田中知成, 福原浩之, 中嶋元, 木村良晴
  • Organizer: 第22回バイオ・高分子シンポジウム
  • Place of Presentation: 東京大学
  • Year and Date: 2012-06-25
• [Presentation] 糖修飾ポリ乳酸の保護基フリー合成と会合挙動解析 (2012)
  • Author(s): 田中知成, 福原浩之, 中嶋元, 木村良晴
  • Organizer: 第22回バイオ・高分子シンポジウム
  • Place of Presentation: 東京大学(東京都)(発表確定)
  • Year and Date: 2012-06-25
• [Presentation] 無保護糖直接活性化法とクリックケミストリーによるオリゴ糖修飾ポリ乳酸の保護基フリー合成 (2012)
  • Author(s): 田中知成, 福原浩之, 中嶋元, 木村良晴
  • Organizer: 第61回高分子学会年次大会
  • Place of Presentation: パシフィコ横浜
  • Year and Date: 2012-05-29
• [Presentation] 無保護糖直接活性化法とクリックケミストリーによるオリゴ糖修飾ポリ乳酸の保護基フリー合成 (2012)
  • Author(s): 田中知成, 福原浩之, 中嶋元, 木村良晴
  • Organizer: 第61回高分子学会年次大会
  • Place of Presentation: パシフィコ横浜(神奈川県)(発表確定)
  • Year and Date: 2012-05-29
• [Presentation] オリゴ糖鎖に適用可能な糖鎖高分子の保護基フリー合成 (2011)
  • Author(s): 福原浩之, 田中知成, 木村良晴
  • Organizer: 第1回4大学連携研究フォーラム
  • Place of Presentation: 京都工芸繊維大学
  • Year and Date: 2011-12-09
• [Presentation] オリゴ糖鎖に適用可能な糖鎖高分子の保護基フリー合成 (2011)
  • Author(s): 福原浩之, 田中知成, 木村良晴
  • Organizer: 第1回4大学連携研究フォーラム
  • Place of Presentation: 京都工芸繊維大学(京都府)
  • Year and Date: 2011-12-09
• [Presentation] 糖による末端修飾ポリ乳酸の保護基フリー合成 (2011)
  • Author(s): 福原浩之, 田中知成, 木村良晴
  • Organizer: 第60回高分子討論会
  • Place of Presentation: 岡山大学
  • Year and Date: 2011-09-30
• [Presentation] オリゴ糖による末端修飾ポリ乳酸の保護基フリー合成 (2011)
  • Author(s): 福原浩之, 田中知成, 木村良晴
  • Organizer: 第60回高分子討論会
  • Place of Presentation: 岡山大学(岡山県)
  • Year and Date: 2011-09-30
• [Presentation] 水溶性脱水縮合剤を活用する高分子量オリゴ糖鎖のラベル化 (2010)
  • Author(s): 小林厚志, 永井光, 田中知成, 石原正規, 野口真人, 正田晋一郎
  • Organizer: 第59回高分子討論会
  • Place of Presentation: 北海道大学
  • Year and Date: 2010-09-15