Peptide isostere formation by zinc carbenoid-mediated chain extension

ORGN 546

Charles K. Zercher, ckz@christa.unh.edu1, Weimin Lin, wlin@cisunix.unh.edu2, Nancy L. Tryder1, Cory R. Theberge1, Fan Su1, and Qinglin Pu1. (1) Department of Chemistry, University of New Hampshire, Parsons Hall, Durham, NH 03824, (2) Chemistry, University of New Hampshire, Parsons Hall, 23 College Rd., Durham, NH 03824
A one-pot zinc-mediated chain extension reaction is utilized for the conversion of amino acid substrates to ketomethylene isosteric replacements for the peptide bond. Three tandem reactions have been developed to facilitate the stereocontrolled incorporation of ?-substituents. The application of the strategy to a mimic of the human CMV protease cleavage site has been developed.
 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008