Iterative, aqueous synthesis of β3-oligopeptides

ORGN 879

Nancy Carrillo, ncarrillo@chem.ucsb.edu, Eric A. Davalos, and Jeffrey W. Bode, bode@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106-9510
Based on our recently developed ketoacid–hydroxyamine peptide ligation, we have developed a new approach to the synthesis of β3-oligopeptides. This iterative peptide coupling is unique in that it requires no coupling reagents or side chain protection groups, proceeds in water, and produces no reaction by-products. The key reaction is the coupling of readily prepared, enantiopure isoxazolidine monomers with α-ketoacids. Improvements in the iterative coupling process and the synthesis of a variety of β3-oligopeptides will be presented.

 

Proteins, Peptides, Amino Acids, and Enzyme Inhibitors
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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