Synthesis of Sansalvamide A derivatives

ORGN 425

Emily Parry, Joseph Brown, Irene Medina, imedina_@hotmail.com, Chris Carroll, chris@the-carrolls.com, and Shelli McAlpine. Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Dr, San Diego, CA 92182
Sansalvamide is a depsipeptide that belongs to a class of biologically active molecules exhibiting anticancer activity. Because little is known about the mechanism of action of Sansalvamide A, the structure-activity relationship between the active compounds and its biological target may provide information for the development of a new class of anticancer agents. We are synthesizing derivatives of Sansalvamide A using both L and D amino acids. Coupling a tripeptide and a dipeptide forms linear pentapeptides, which are then cyclized to form Sansalvamide derivates. All compounds are confirmed via LCMS and NMR. These compounds are submitted for biological assays with a collaborator who discovered the initial natural product, thus allowing us to compare the structure activity relationship of these derivatives to those of the natural product.