title: Oligo(N-alkoxy glycines): trans substantiating peptoid conformations.
abstract: Peptoid oligomers possess many desirable attributes bioactive peptidomimetic agents, including their ease of synthesis, chemical diversity, and capability for molecular recognition. Ongoing efforts to develop functional peptoids will necessitate improved capability for control of peptoid structure, particularly of the backbone amide conformation. We introduce alkoxyamines as a new reagent for solid phase peptoid synthesis. Herein, we describe the synthesis of N-alkoxy peptoids, and present NMR data indicating that the oligomers adopt a single stable conformation featuring trans amide bonds. These findings, combined with results from computational modeling, suggest that N-alkoxy peptoid oligomers have a strong propensity to adopt a polyproline II type secondary structure.
authors.affiliation: Department of Chemistry, New York University, NY 10003, USA.
authors.forename: Peter A
authors.initials: PA
authors.lastname: Jordan
authors.forename: Bishwajit
authors.initials: B
authors.lastname: Paul
authors.forename: Glenn L
authors.initials: GL
authors.lastname: Butterfoss
authors.forename: P Douglas
authors.initials: PD
authors.lastname: Renfrew
authors.forename: Richard
authors.initials: R
authors.lastname: Bonneau
authors.forename: Kent
authors.initials: K
authors.lastname: Kirshenbaum
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002942:Circular Dichroism; D003198:Computer Simulation; D005998:Glycine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry; D011487:Protein Conformation
chemical_list: D000438:Alcohols; D034444:Peptoids; C059688:alkoxyl radical; D005998:Glycine