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 journalArticle

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

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Peptoids
Oligomers
Chirality
X ray crystallography
X Ray Crystallography
Energy barriers
Dichroism
Circular Dichroism
Purification
Nitrogen
Carbon
Monomers
High Pressure Liquid Chromatography
Nuclear magnetic resonance

ASJC Scopus subject areas

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

Cite this

Paul, B., Butterfoss, G. L., Boswell, M. G., Renfrew, P. D., Yeung, F. G., Shah, N. H., ... Kirshenbaum, K. (2011). Peptoid atropisomers. Journal of the American Chemical Society, 133(28), 10910-10919. https://doi.org/10.1021/ja2028684

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

In: Journal of the American Chemical Society, Vol. 133, No. 28, 20.07.2011, p. 10910-10919.

Research output: Contribution to journalArticle

Paul, B, Butterfoss, GL, Boswell, MG, Renfrew, PD, Yeung, FG, Shah, NH, Wolf, C, Bonneau, R & Kirshenbaum, K 2011, 'Peptoid atropisomers', Journal of the American Chemical Society, vol. 133, no. 28, pp. 10910-10919. https://doi.org/10.1021/ja2028684
Paul B, Butterfoss GL, Boswell MG, Renfrew PD, Yeung FG, Shah NH et al. Peptoid atropisomers. Journal of the American Chemical Society. 2011 Jul 20;133(28):10910-10919. https://doi.org/10.1021/ja2028684
Paul, Bishwajit ; Butterfoss, Glenn L. ; Boswell, Mikki G. ; Renfrew, P. Douglas ; Yeung, Fanny G. ; Shah, Neel H. ; Wolf, Christian ; Bonneau, Richard ; Kirshenbaum, Kent. / Peptoid atropisomers. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 28. pp. 10910-10919.
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