Integrated Synthesis of Glycans Using Microfluidic and Solid-phase Methods

2014 Fiscal Year Final Research Report

• Project Area: Organic Synthesis based on Integration of Chemical Reactions. New Methodologies and New Materials
• Project/Area Number: 21106008
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Osaka University
• Principal Investigator: FUKASE Koichi 大阪大学, 理学(系)研究科(研究院), 教授 (80192722)
• Project Period (FY): 2009-04-01 – 2015-03-31
• Keywords: マイクロフロー / 固相合成 / N-グリカン / 自然免疫リガンド / グリコシル化

Outline of Final Research Achievements

We have investigated the synthesis of various glycans from both animals and microbes in order to investigate their biological functions. The former targets are the N-glycans containing core fucose, bisecting glucosamine or bis-sialylated motif. The key issues for the synthesis were stereoselective glycosylation reactions and we developed highly efficient methods by using microfluidic conditions. We then achieved the solid-phase synthesis of sialylated N-glycan.
Microbial glycoconjugates such as partial structures of lipopolysaccharide (LPS) and peptidoglycan (PGN) from bacteria as well as inositol phospholipids from Entamoeba histolytica were also synthesized. For the synthesis of E. histolytica phospholipids, we developed new synthetic methods including regioselective phosphorylation and synthesis of the long-chain fatty acids by Ni catalyzed sp3-sp3 cross coupling reaction. We also adopted a new protecting group strategy utilizing allyl group as the permanent protecting group.

Free Research Field

天然物有機化学