Title: “Sweet chemistry” at the interface of chemistry and biochemistry
By: Prof. Qingjiang (Vince) Li
Department of Chemistry, University of Massachusetts Boston
Abstract: Carbohydrates are ubiquitous on the cell surface. They mediate cell―cell recognition and are involved in many fundamental biological processes such as fertilization, and immune response etc. While continuously making advances, the investigation on the biological roles of glycans and post-translational modification of proteins in biological and disease processes is bottlenecked by synthesis, which is tasked to provide structurally complex and diverse carbohydrate molecules for related biological studies. The chemical synthesis of carbohydrates typically requires lengthy route of protection/deprotection for regio-selectivity, sophisticated strategy for stereo control, as well as experience and expertise of the practitioners, whereas the enzymatic synthesis is limited by the availability of enzymes and sugar nucleotides.
This presentation will broadly cover the chemical and enzymatic synthesis of carbohydrates, starting with two individual projects that were completed during my postdoctoral research. In the first project, a complex carbohydrate-based cancer antigen KH-1 was obtained via total synthesis, while the second project was to develop a divergent method to access a variety of glycosphingolipids by chemoenzymatic approach. At the end, how these chemical and enzymatic synthesis projects are developed into the current project of project of methodology development towards the streamlined assembly of glycomimetic will be briefly discussed.
