Design and Synthesis of Novel Immunostimulatory Molecules Based on α-Galactosyl Ceramides

• Project/Area Number: 23880011
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Gifu University
• Principal Investigator: IMAMURA Akihiro 岐阜大学, 応用生物科学部, 助教 (30610951)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000); Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2011: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: 糖脂質 / 免疫賦活 / 有機合成 / NKT細胞 / ガラクトシルセラミド / グリコシル化 / 抗腫瘍 / 糖鎖 / 免疫学 / 複合糖質

Research Abstract

Novel immunostimulators based on α-galactosyl ceramides were designed and synthesized by using a unique synthetic method developed by our group. Synthesis of α-galactoside/galactosaminide as a key structure was efficiently accomplished by DTBS-directed α-galactosylation developed by us. Fully protected framework of a target molecule was synthesized successfully. Unfortunately, however, poor soluble property of the target molecule produced after deprotection obliged us to redesign the structure of target molecules. We are currently trying to synthesize the redesigned molecule that is shortened the length of fatty acid in the ceramide moiety.