Peptoid atropisomers

Bishwajit Paul, Glenn L. Butterfoss, Mikki G. Boswell, P. Douglas Renfrew, Fanny G. Yeung, Neel H. Shah, Christian Wolf, Richard Bonneau, Kent Kirshenbaum

Research output: Contribution to journalArticlepeer-review

Abstract

We report the isolation of N-aryl peptoid oligomers that adopt chiral folds, despite the absence of chiral centers. Peptoid monomers incorporating ortho-substituted N-aryl side chains are identified that exhibit axial chirality. We observe significant energy barriers to rotation about the stereogenic carbon-nitrogen bond, allowing chromatographic purification of stable atropisomeric forms. We study the atropisomerism of N-aryl peptoid oligomers by computational modeling, NMR, X-ray crystallography, dynamic HPLC, and circular dichroism. The results demonstrate a new approach to promote the conformational ordering of this important class of foldamer compounds.

Original languageEnglish (US)
Pages (from-to)10910-10919
Number of pages10
JournalJournal of the American Chemical Society
Volume133
Issue number28
DOIs
StatePublished - Jul 20 2011

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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