Chemical Synthesis Core C

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Core C Chemical Synthesis Core Leader: Adriaan Minnaard ABSTRACT The Chemical Synthesis Core C supports chemical discovery and benchmarking experiments in ways that cannot be achieved by analysis natural bacterial products. Whereas natural compounds from pathogenic mycobacteria are generally limited to microgram yields, chemical synthesis can provide many milligrams to durably supply large-scale experiments. Whereas natural products typically show many nearly co-eluting molecular variants, synthesis can produce a single pure compound for benchmarking natural compounds and as a standard for rigorously confirming newly discovered chemical structures. Synthesis of analogs with defined chemical variations supports determination of structure-activity relationships. Core C is housed at the Stratingh Institute at the University of Groningen, a world leading center for synthetic chemistry in a laboratory that specializes in enantiospecific catalytic methods of chemical synthesis. Thus, Core C has a unique expertise in production of bacterial metabolites with multiple chiral centers that define complex branched chain structures, such as phthiocerol dimycocerosate, sulfoglycolipids, mycolic acid, phenolic glycolipid and other lipids. Core C will produce milligram quantities of mycobacterial metabolites to support Projects 1 and 3. In addition, the Core will provide both existing and new compounds to generate a comprehensive set of standards for benchmarking mycobacterial lipids in the Profiling and Mapping Core B.