Cell-Surface Glycoconjugates II

本研究的重点是利用氨基酸作为合成细胞表面碳水化合物的起始材料的合成方法的发展，以及基于机制的碳水化合物加工酶抑制剂。目标包括氮杂糖、吲哚吡啶和吡咯利西啶生物碱。目前的方法将扩展到生产岩藻脂生物合成抑制剂和复杂的生物碱，如石蒜碱。此外，希夫碱将用于生产偶氮- c -糖苷，udp -半乳糖和GDP聚焦类似物，作为糖基转移酶抑制剂。希夫碱还将用于合成光学纯的c2对称手性配体，这些配体在不对称金属催化的环氧化反应中有潜在的应用前景。有了这个更新奖，合成有机项目支持亚利桑那大学化学系的罗宾·l·波尔特博士的研究。波尔特教授将集中研究糖苷酶和糖转移酶抑制剂的合成。这些抑制剂对研究细胞表面碳水化合物的生物合成具有重要意义。

The focus of this research is the development of synthetic methodology using amino acids as starting materials for the synthesis of cell-surface carbohydrates, and the mechanism-based inhibitors of carbohydrate processing enzymes. Targets include aza-sugars, indolizidine and pyrrolizidine alkaloids. Current methods will be extended to produce fucolipid biosynthesis inhibitors and complex alkaloids such as lycoricidine. Also, Schiff bases will be used to produce aza-C-glycoside, UDP-galactose and GDP-fucose analogs to serve as glycosyltransferase inhibitors. Schiff bases will also be used to synthesize optically pure C2-symmetric chiral ligands, ligands that have potential for use in asymmetric, metal catalyzed epoxidations. With this renewal award, the Synthetic Organic Program is supporting the research of Dr. Robin L. Polt of the Department of Chemistry at the University of Arizona. Professor Polt will focus his research on the synthesis of glycosidase and glycotransferase inhibitors. These inhibitors are important for the study of the biosynthesis of cell-surface carbohydrates.