Glycosylation without adding any acid catalysts -Synthesis and organization of impossible oligosaccharide glycolipids-

2014 Fiscal Year Final Research Report

• Project/Area Number: 25620092
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Polymer chemistry
• Research Institution: Tohoku University
• Principal Investigator: SHODA Shin-ichiro 東北大学, 工学(系)研究科(研究院), 教授 (10143364)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Keywords: 糖脂質 / トリアジン誘導体 / 水素添加 / グリコシル化 / 立体選択性 / オリゴ糖 / 酸触媒 / アノマー直接活性化

Outline of Final Research Achievements

Glycolipids play important roles in cell processes such as bio-recognition on the cell membranes.Chemically, amphiphilic glycolipids can self-assemble into 3D architectures that are attractive smart hydrogels for biomolecular microarrays and dug delivery. Meanwhile, vinyl-contained glycolipid is potential monomer for the synthesis of glycopolymer, synthetic polymer with saccharide pendants, and has received considerable attention in the fields of material science and biomedicine. We have developed a reductive synthetic method towards glycolipid by the alcoholysis of the one-step preparable glycosyl donor,4,6-dibenzyloxy-1,3,5-triazin-2-yl glycosides under reductive conditions, without adding any acid catalysts. Through this reaction, glycosidic bonds between oligosaccharides and alcohols were constructed with the site specific activation at the reducing end under extremely mild reaction conditions, which had been impossible to carry out for a long time.

Free Research Field

高分子合成