Design and synthesis of fluorescent glycolipid photoaffinity probes and their photoreactivity.
Kaori Sakurai, Tamayo Yamaguchi, Sakae Mizuno
Author Information
Kaori Sakurai: Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Naka-cho, 2-24-16, Koganei, Tokyo 184-8588, Japan. Electronic address: sakuraik@cc.tuat.ac.jp.
Tamayo Yamaguchi: Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Naka-cho, 2-24-16, Koganei, Tokyo 184-8588, Japan.
Sakae Mizuno: Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Naka-cho, 2-24-16, Koganei, Tokyo 184-8588, Japan.
Glycolipid-protein interactions at the cell surface are implicated in various biological processes. Toward the investigation of glycolipid binding proteins, we designed and synthesized trifunctional photoaffinity probes, which present a sugar head group with a triazole linkage to the lipid tail unit containing a photoreactive group and a fluorescent tag. The glycolipid photoaffinity probes bearing benzophenone group or diazirine group were evaluated for their photocrosslinking reactivity toward a carbohydrate head group specific protein. The diazirine based glycolipid photoaffinity probe was found to be more effective than the benzophenone-based probe in a comparative analysis involving a competitive ligand to distinguish a specific binding protein.
