Oligo(N-alkoxy glycines): trans substantiating peptoid conformations.

Peter A. Jordan, Bishwajit Paul, Glenn L. Butterfoss, P. Douglas Renfrew, Richard Bonneau, Kent Kirshenbaum

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)617-626
Number of pages10
JournalBiopolymers
Volume96
Issue number5
DOIs
StatePublished - 2011

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Biomaterials
  • Organic Chemistry

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