1,2-cis aminoglycoside synthesis by anomerization stragegy

2017 Fiscal Year Final Research Report

• 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
• Keywords: アミノ糖 / エンド開裂 / ミコチオール / GPI アンカー

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.

Free Research Field

有機化学、糖化学