Solid-phase synthesis of a biologically active phalloidin analog

ORGN 593

Laura A. Schuresko, kapitzky@chemistry.ucsc.edu and R. Scott Lokey, lokey@chemistry.ucsc.edu. Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, CA 95060
Phalloidin is a toxic, bicyclic heptapeptide found in the Death Cap mushroom (Amanita phalloides). When ingested, phalloidin binds to F-actin present in the liver and kidneys, decreasing the activity of these organs and causing renal failure and eventual death. Fluorescent phalloidin derivatives can be used to label cellular F-actin in vitro, enabling visualization of the cytoskeleton by fluorescence microscopy. This is convenient for the analysis of cell-based assays where changes to the actin cytoskeleton are being monitored. Here we describe a simple, high-yielding synthesis for a fluorescent phalloidin analog, featuring the novel use of a thioether-forming reaction.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006