1,2-cis aminoglycoside synthesis by anomerization stragegy

• Project/Area Number: 15K07882
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Institute of Physical and Chemical Research
• Principal Investigator: Manabe Shino 国立研究開発法人理化学研究所, 伊藤細胞制御化学研究室, 専任研究員 (60300901)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: アミノ糖 / エンド開裂 / ミコチオール / GPI アンカー / 糖 / アミノグリコシド / mycothiol / 異性化反応 / 抗結核 / 化学合成

Outline of Final Research Achievements

In glycosylation reaction, 1,2-cis selective glycosylation of aminoglycosides is still an unsolved issue. We have found endocyclic cleavage reaction proceeds when 2,3-trans carbamate group is introduced. In endocyclic cleavage reaction, the bond between anomeric carbon and O5 is cleaved, and 1,2-cis glycosides are generated after cyclization. In this project, synthetic utility of endocyclic reaction was demonstrated though mycothiol synthesis. Furthermore, efficacy between direct glycosylation reaction and anomerization via endocyclic cleavage was compared.

Research Products

• [Int'l Joint Research] Toledo University(米国)
• [Int'l Joint Research] Toledo University(米国)
• [Journal Article] Comparing of Endocyclic and Exocyclic Cleavage Reactions Using Mycothiol Synthesis as an Example (2018)
  • Author(s): Shino Manabe, Yukishige Ito
  • Journal Title: Tetrahedron Volume: 74 Issue: 20 Pages: 2440-2446
  • DOI: 10.1016/j.tet.2018.03.069
  • Peer Reviewed
• [Journal Article] Amide Bond Formation of Sialic Acid in Oligosaccharide without Protecting Group (2018)
  • Author(s): Shino Manabe, Junpei Abe, Yukishige Ito
  • Journal Title: HeteroCycles Volume: 印刷中 Issue: 2 Pages: 1203-1203
  • DOI: 10.3987/com-18-s(t)69
  • Peer Reviewed
• [Journal Article] Synthetic utility of endocyclic cleavage reaction (2017)
  • Author(s): Shino Manabe, Yukishige Ito
  • Journal Title: Pure and Applied Chemistry Volume: 印刷中 Issue: 7 Pages: 899-909
  • DOI: 10.1515/pac-2016-0917
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Mycothiol synthesis by an anomerization reaction through endocyclic cleavage (2016)
  • Author(s): Shino Manabe, Yukishige Ito
  • Journal Title: Beilstein J. Org. Chem. Volume: 12 Pages: 328-333
  • DOI: 10.3762/bjoc.12.35
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Presentation] 常識にとらわれない糖化学 (2017)
  • Author(s): 眞鍋 史乃
  • Organizer: 有機合成化学協会関東支部ミニシンポジウム多摩2017
  • Invited
• [Presentation] Synthesis of 1,2-cis aminoglycoside containing oligosaccharides by endocyclic cleavage reaction (2017)
  • Author(s): Shino Manabe, Yukishige Ito
  • Organizer: Systems Glycobiology and Beyond, RIKEN International Symposium
  • Int'l Joint Research
• [Presentation] 糖化学からの展開：切断機構の解明からバイオ医薬品へ (2016)
  • Author(s): 眞鍋史乃
  • Organizer: 第14回有機合成化学談話会（湯河原セミナー）
  • Place of Presentation: 和光純薬工業湯河原研修所、熱海市
  • Year and Date: 2016-09-23
  • Invited
• [Presentation] 糖化学からの展開：切断機構の解明からバイオ医薬品へ (2016)
  • Author(s): 眞鍋史乃
  • Organizer: 第14回有機合成化学談話会
  • Place of Presentation: 熱海、和光純薬工業（株）湯河原研修所
  • Year and Date: 2016-09-23
  • Invited
• [Presentation] 1,2-cis アミノグリコシド合成のおける直接法と異性化法の比較 (2016)
  • Author(s): 眞鍋史乃、伊藤幸成
  • Organizer: 第35回日本糖質学会年会
  • Place of Presentation: 高知市文化プラザ、高知市
  • Year and Date: 2016-09-01
• [Presentation] Synthetic utility of endocyclic cleavage reaction (2016)
  • Author(s): Shino Manabe, Yukishige Ito
  • Organizer: International Carbohydrate Symposium 2016
  • Place of Presentation: New Marriott Hotel, New Orleans, LA, USA
  • Year and Date: 2016-07-17
  • Int'l Joint Research
• [Presentation] Endocyclic Cleavage Reaction: Evidence and Synthetic Utility (2016)
  • Author(s): Shino Manabe
  • Organizer: RIKEN-MAX PLANCK Symposium, Fifth Annual Symposium
  • Place of Presentation: Berlin
  • Year and Date: 2016-04-19
  • Int'l Joint Research / Invited
• [Book] Carbohydrate Chemistry, Proven Synthetic Methods (2017)
  • Author(s): Shino Manabe
  • Total Pages: 369
  • Publisher: CRC Press
• [Book] Carbohydrate Chemistry: Proven Methods (2017)
  • Author(s): Shino Manabe
  • Total Pages: 287
  • Publisher: CRC-press