Development of an Automated Synthesizer of Oligosaccharides Based on the Electrochemical Method

• Project/Area Number: 25410115
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Tottori University
• Principal Investigator: Nokami Toshiki 鳥取大学, 工学(系)研究科(研究院), 准教授 (60402963)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000); Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2013: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
• Keywords: 糖鎖 / 自動合成 / 有機化学 / 電解合成 / 電解酸化 / グリコシル化 / 天然物

Outline of Final Research Achievements

To synthesize biologically active oligosaccharide efficiently, we have developed an automated synthesizer for oligosaccharide based on electrochemical method. Carbohydrate building blocks used in this study were stable, easy to handle, and easy to prepare. It is also easy to perform large-scale synthesis and analyze the reactions, because the method is based on solution-phase synthesis. We expect that the synthesizer can be a popular edition of an automated oligosaccharide synthesizer, which is available in reasonable price.

Research Products

• [Int'l Joint Research] 国立交通大学(台湾)
• [Journal Article] The β-Silyl Effect on the Memory of Chirality in Friedel-Crafts Alkylation Using Chiral α-Aryl Alcohols (2015)
  • Author(s): Nokami, T.; Yamane, Y.; Oshitani, S.; Kobayashi, J.; Matsui, S.; Nishihara, T.; Uno, H.; Hayase, S.; Itoh, T.
  • Journal Title: Organic Letters Volume: Vol. 17 Issue: 12 Pages: 3182-3185
  • DOI: 10.1021/acs.orglett.5b01582
  • Peer Reviewed
• [Journal Article] Development of n-Type Semiconductor Based on Cyclopentene or Cyclohexene-fused [C60]-Fullerene Derivatives (2015)
  • Author(s): Yamane, Y.; Sugawara, K.; Nakamura, N.; Hayase, S.; Nokami, T.; Itoh, T.
  • Journal Title: Journal of Organic Chemistry Volume: Vol. 80 Issue: 9 Pages: 4638-4649
  • DOI: 10.1021/acs.joc.5b00530
  • Peer Reviewed
• [Journal Article] Copper Ion Containing Ionic Liquids Provides Improved Endurance and Switching Voltage Distributions of Conducting-Bridge Random Access Memory (2015)
  • Author(s): Akinori Harada, Hiroki Yamaoka, Kouhei Watanabe, Kentaro Kinoshita, Satoru Kishida, Yukinobu Fukaya, Toshiki Nokami, Toshiyuki Itoh
  • Journal Title: Chemistry Letter Volume: 44 Issue: 11 Pages: 1578-1580
  • DOI: 10.1246/cl.150773
  • NAID: 130005108105
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Electrochemical Na-insertion/extraction properties of phosphorus electrodes in ionic liquid electrolytes (2015)
  • Author(s): Shimizu, M.; Usui, H.; Yamane, K.; Sakata, T.; Nokami, T.; Itoh, T.; Sakaguchi, H.
  • Journal Title: International Journal of Electrochemcal Science Volume: Vol. 10 Pages: 10132-10144
  • NAID: 120005868799
  • Peer Reviewed
• [Journal Article] Phosphonium alkyl PEG sulfate ionic liquids as coating materials for activation of Burkholderia cepacia lipase (2015)
  • Author(s): Matsubara, Y.; Kadotani, S.; Nishihara, T.; Hikino, Y.; Fukaya, Y.; Nokami, T.; Itoh, T.
  • Journal Title: Biotechnology Journal Volume: Vol. 10 Issue: 12 Pages: 1944-1951
  • DOI: 10.1002/biot.201500413
  • Peer Reviewed
• [Journal Article] Automated Electrochemical Assembly of the Protected Potential TMG-chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block. (2015)
  • Author(s): Nokami, T.; Isoda, Y.; Sasaki, N.; Takaiso, A.; Hayase, S.; Itoh, T.; Hayashi, R.; Shimizu, A.; Yoshida, J.
  • Journal Title: Organic Letters Volume: 17 Issue: 6 Pages: 1525-1528
  • DOI: 10.1021/acs.orglett.5b00406
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Redox Active Dendronized Polystyrenes Equipped with Peripheral Triarylamines (2014)
  • Author(s): 野上敏材、武者直樹、諸藤達也、武田圭司、宅見正浩、清水章弘、吉田潤一
  • Journal Title: Beilstein Journal of Organic Chemistry Volume: 10 Pages: 3079-3103
  • DOI: 10.3762/bjoc.10.326
  • NAID: 120005540401
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System. (2014)
  • Author(s): Nokami, T.; Matsumoto, K.; Itoh, T.-a.; Fukaya, Y.; Itoh, T.
  • Journal Title: Organic Process Research & Development Volume: 18 Issue: 11 Pages: 1367-1371
  • DOI: 10.1021/op500131u
  • Peer Reviewed
• [Journal Article] Synthesis of gem-Difluoromethylene Building Blocks through Regioselective Allylation of gem-Difluorocyclopropanes (2014)
  • Author(s): Munemori, D.; Narita, K.; Nokami, T.; Itoh, T.
  • Journal Title: Organic Letters Volume: 16 Issue: 10 Pages: 2638-2641
  • DOI: 10.1021/ol500803r
  • Peer Reviewed
• [Journal Article] Recent Progress of Chemical Glycosylations and Oligosaccharide Synthesis (2014)
  • Author(s): 野上敏材
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan Volume: 72 Issue: 7 Pages: 797-807
  • DOI: 10.5059/yukigoseikyokaishi.72.797
  • NAID: 130004679610
  • ISSN: 0037-9980, 1883-6526
  • Peer Reviewed
• [Journal Article] Nitrogen-Containing Polycyclic Quinones as Cathode Materials for LIB. Improving Voltage by Electronegativity and Litium Coordination (2014)
  • Author(s): Shimizu, A.; Tsujii, Y.; Kuramoto, H.;Nokami, T.; Inatomi, Y.; Hojo, N.; Yoshida, J.
  • Journal Title: Energy Technol. Volume: 2 Issue: 2 Pages: 155-158
  • DOI: 10.1002/ente.201300148
  • Peer Reviewed
• [Journal Article] Automated Solution-Phase Synthesis of Oligosaccharides via Iterative electrochemical Assembly of Thioglycosides (2013)
  • Author(s): Nokami, T.; Hayashi, R.; Saigusa, Y.; Shimizu, A.; Liu, C.-Y.; Mong, K.-K. T.; Yoshida, J.
  • Journal Title: Org. Lett. Volume: 15 Issue: 17 Pages: 4520-4523
  • DOI: 10.1021/ol402034g
  • Peer Reviewed
• [Journal Article] Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization (2013)
  • Author(s): Ashikari, Y.; Shimizu, A.; Nokami, T.; Yoshida, J.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 43 Pages: 16070-16073
  • DOI: 10.1021/ja4092648
  • Peer Reviewed
• [Presentation] Automated Electrochemical Assembly for Oligosaccharide Synthesis (2015)
  • Author(s): Toshiki Nokami, Yuta Isoda, Keisuke Takayanagi, Norihiko Sasaki, Shuichi Hayase, Toshiyuki Itoh
  • Organizer: Pacifichem2015
  • Place of Presentation: ヒルトンハワイアンビレッジ、ホノルル、アメリカ合衆国
  • Year and Date: 2015-12-19
  • Int'l Joint Research / Invited
• [Presentation] Electrochemical Method as an Enabling Tool for Glycosylation (2015)
  • Author(s): Toshiki Nokami, Yuta Isoda, Norihiko Sasaki, Shuichi Hayase, Toshiyuki Itoh, Ryutaro Hayashi, Akihiro Shimizu, Jun-ichi Yoshida
  • Organizer: Pacifichem2015
  • Place of Presentation: ヒルトンハワイアンビレッジ、ホノルル、アメリカ合衆国
  • Year and Date: 2015-12-17
  • Int'l Joint Research
• [Presentation] 12)電解グリコシル化反応の精製プロセス迅速化を指向したイオン液体タグの開発 (2015)
  • Author(s): 佐々木紀彦、野上敏材、伊藤敏幸
  • Organizer: 2015年日本化学会中国四国支部大会
  • Place of Presentation: 岡山大学
  • Year and Date: 2015-11-15
• [Presentation] TMG-キトトリオマイシンの全合成 (2015)
  • Author(s): 磯田悠太、佐々木紀彦、野上敏材、早瀬修一、伊藤敏幸
  • Organizer: 2015年日本化学会中国四国支部大会
  • Place of Presentation: 岡山大学
  • Year and Date: 2015-11-15
• [Presentation] Automated Electrochemical Assembly of Oligosaccharides (2015)
  • Author(s): Toshiki Nokami, Yuta Isoda, Norihiko Sasaki, Toshiyuki Itoh, Ryutaro Hayashi, Akihiro Shimizu, Jun-ichi Yoshida
  • Organizer: IKCOC-13
  • Place of Presentation: リーガロイヤルホテル京都、京都
  • Year and Date: 2015-11-12
  • Int'l Joint Research
• [Presentation] Reformatsky 反応と向山アルドール反応を鍵反応とするポイントフッ素化糖の De Novo合成 (2015)
  • Author(s): 高柳恵輔、原田晃典、野上敏材、伊藤敏幸
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 船橋市、日本大学
  • Year and Date: 2015-03-28
• [Presentation] 電解グリコシル化反応のためのベンジルエーテル型イオン液体タグの開発 (2015)
  • Author(s): 佐々木紀彦、野上敏材、伊藤敏幸
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 船橋市、日本大学
  • Year and Date: 2015-03-27
• [Presentation] TMG-キトトリオマイシン四糖液相電解自動合成のための糖鎖ビルディングブロックと反応条件の最適化 (2015)
  • Author(s): 磯田悠太、早瀬修一、野上敏材、伊藤敏幸
  • Organizer: 日本化学会第95春季年会
  • Place of Presentation: 船橋市、日本大学
  • Year and Date: 2015-03-26
• [Presentation] オリゴ糖の液相自動合成を目指して (2014)
  • Author(s): 野上敏材
  • Organizer: 日本化学会中国四国支部大会
  • Place of Presentation: 山口市、山口大学
  • Year and Date: 2014-11-08
  • Invited
• [Presentation] The scope and limitations of electrochemical assembly of oligosaccharides (2014)
  • Author(s): 野上敏材
  • Organizer: Asia-Canada Glycoscience Meeting
  • Place of Presentation: バンクーバー、カナダ
  • Year and Date: 2014-05-31
  • Invited
• [Presentation] Electrochemical assembly for oligosaccharide synthesis (2014)
  • Author(s): Toshiki Nokami
  • Organizer: 247th ACS Meeting
  • Place of Presentation: Dallas, Texas, USA
  • Invited
• [Presentation] オリゴグルコサミンの電解自動合成を指向した糖鎖ビルディングブロックの開発 (2014)
  • Author(s): 野上敏材、磯田悠太、伊藤敏幸、林竜太朗、吉田潤一
  • Organizer: 電気化学会第81回大会
  • Place of Presentation: 関西大学、大阪
• [Presentation] The scope and limitations of electrochemical assembly of oligosaccharides (2014)
  • Author(s): Toshiki Nokami
  • Organizer: Asia-Canada Glycosicence Meeting
  • Place of Presentation: Vancouver, Canada
  • Invited
• [Presentation] Electrochemical method as an enabling tool for glycosylation (2013)
  • Author(s): Toshiki Nokami
  • Organizer: Gordon Resaerch Conference
  • Place of Presentation: Mt. Snow Resort, Vermont, USA
  • Invited
• [Presentation] 電気化学的手法によるオリゴグルコサミンの自動合成 (2013)
  • Author(s): 野上敏材、林竜太朗、吉田潤一
  • Organizer: 第32回日本糖質学会年会
  • Place of Presentation: 大阪国際交流センター、大阪
• [Book] 糖鎖の新機能開発・応用ハンドブック 創薬・医療から食品開発まで (2015)
  • Author(s): 野上敏材、他多数
  • Total Pages: 628
  • Publisher: 株式会社 エヌ・ティー・エス
• [Patent(Industrial Property Rights)] 立体選択的な糖鎖の製造方法 (2016)
  • Inventor(s): 野上敏材
  • Industrial Property Rights Holder: 野上敏材
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2016-064646
  • Filing Date: 2016-03-09