Peptoid oligomers incorporating N-alkoxy sidechains

ORGN 773

Peter A Jordan, paj229@nyu.edu, Paramjit S. Arora, arora@nyu.edu, and Kent Kirshenbaum, kent@nyu.edu. Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003
N-substituted glycine oligomers, or peptoids, are capable of adopting stable secondary structures, despite their inability to form intramolecular hydrogen bonds networks. Previous studies have demonstrated that bulky chiral amines can be used as “submonomers” to synthesize N-alkylated glycine oligomers with a preference for helical conformations including repeating cis amide bonds. We seek to expand the structural diversity of peptoid oligomers in an effort to discover new secondary structure motifs. We present the synthesis and characterization of novel peptoid oligomers in which an O-substituted hydroxyl amine, such as O-benzylhyrdroxylamine, is incorporated as a peptoid side chain using a modified submonomer protocol.