New approaches in the characterization and modification of peptoid oligomers

ORGN 235

Kent Kirshenbaum, Department of Chemistry, Department of Chemistry, New York University, 100 Washington Square East, Room 1001, New York, NY 10003
We describe recent efforts to enhance the structural and functional capabilities of N-substituted glycine oligomers, or “peptoids”. These studies include: the efficient sequencing of peptoid oligomers using ion-trap LC/MS/MS techniques; the use of protected α-amino acids as submonomers for peptoid synthesis facilitating the formation of stable helical folds in aqueous solution; the pH dependent conformational rearrangements of these peptoid sequences; the development of ESR spectroscopy to determine distances between peptoid sidechains bearing stable free-radical nitroxides; and the site-specific polyvalent conjugation of diverse substituents onto peptoid sidechains using azide-alkyne [3+2] cycloaddition reactions. These advances will provide some of the tools that we will require for realizing the full biomimetic potential of sequence-specific peptoid oligomers.