Synthesis of chemical probes containing di/oligosialialic acids and their biological evaluation related to innate immunity

2016 Fiscal Year Final Research Report

• Project/Area Number: 26282209
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Biomolecular chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Tanaka Hiroshi 東京工業大学, 物質理工学院, 准教授 (40334544)
• Co-Investigator(Renkei-kenkyūsha): YAMAGUCHI Yoshiki 国立研究開発法人理化学研究所, 糖鎖構造生物学研究チーム, チームリーダー (90323451)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 糖鎖 / シアル酸 / 免疫 / グリコシル化 / 高分子

Outline of Final Research Achievements

In this report, we first investigated that partially unprotected sialyl donors underwent a-selective glycosidation without use of an acetonitrile effect. To demonstrate the utility of the method, a straight forward synthesis of α(2,9) disialosides containing N-acetyl and/or N-glycolyl groups was achieved by using the two N-acetyl and N-glycolyl sialyl donors. Next we successfully prepared Glycopolymers possessing disialic acids with a narrow with narrow polydisparities from glycosylated monomers via π-allyl nickel catalyzed coordinating polymerization. A biological evaluation of the glycopolymers and revealed that the synthetic fluoroecent-labelled glycopolymers cause the Siglec-7-GD3 interaction to dissociate in the micromolar concentration range. Finally we prepared the synthesis of dextran derivative possessing disialic acids via polymer reactions. The glycopolymer was able to release Siglec7 from Siglec7-GD3 complex possibly.

Free Research Field

有機化学