Ligation of diverse peptoid sequences

ORGN 600

Barney Yoo, by261@nyu.edu and Kent Kirshenbaum, kent@nyu.edu. Department of Chemistry, New York University, 100 Washington Sq East, New York, NY 10003
We have reported the use of proteases to catalyze the generation of biomimetic macromolecules through the condensation of peptoid fragments. Protease-mediated ligation exploits the inherent proteolytic resistance of peptoids (N-substituted glycine oligomers), coupled with the specificity and catalytic activity of proteases. We now describe the utility of protease-mediated ligation in the synthesis of peptidomimetic oligomers ranging from 11-32 residues, comprised of diverse sequences and side chain functionalities. The ligation reactions can be performed iteratively, enabling the generation of peptoid concatemers – i.e. block segments repeated end-to-end. Our current efforts are directed towards the synthesis of sequence-specific macromolecules comprised of repeating peptoid or hybrid peptoid-peptide segments.

 

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