Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers

ORGN 412

Nicholas G. Angelo, ng207@nyu.edu and Paramjit S. Arora, arora@nyu.edu. Department of Chemistry, New York University, 100 Washington Sq East, New York, NY 10003
We recently described a new class of nonpeptidic foldamers prepared by swapping amide bonds with 1,2,3-triazole linkages using the well-studied copper (I) catalyzed Huisgen cycloaddition reaction between azides and terminal alkynes. The required precursors are derived from naturally occurring amino acids, allowing for the facile incorporation of side chain functionality. These foldamers were studied by 2D NMR and appear to adopt an extended zigzag conformation where neighboring triazole moieties are anti to each other. This poster describes the synthesis and characterization of these foldamers, and suggests their potential as beta-strand mimics.

 

New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006