Synthesis of Carbohydrate Mimics via RCM

Wayne State University, Detroit MI

Investigators

Abstract

The focus of this research is to develop methodology for the preparation of biologically relevant C-saccharides and C-glycoside analogs of carbohydrate contining natural products. One approach uses a ring closing metathesis (RCM)) strategy for the preparation of C-1 glycals, which are, in turn, readily functionalized and transformed into 2-deoxy C-glycosides of 2-gluco-C-glycosides. A second approach uses an iterative tethering-olefin metathesis strategy for the preparation of C-oligosaccharides. With this new award, the Organic and Macromolecular Chemistry Program is supporting the research activities of Dr. Maarten H. Postema of the Department of Chemistry at Wayne State University. Professor Postema will focus his work on developing methodology for the preparation of stable and unique saccharide mimics. Carbohydrates are an important class of organic structures. When joined at the cell surface to form oligosaccharides, they play an important role in cellular recognition, metastasis and adhesion. The stable C-saccharides and C-glycosides generated by the methodology of this project have implications for the pharmaceutical industry. The project also presents an attractive venue for the training of graduates students.