Peptoid Atropisomers

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 stereogeni...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-07, Vol.133 (28), p.10910-10919
Main Authors: Paul, Bishwajit, Butterfoss, Glenn L, Boswell, Mikki G, Renfrew, P. Douglas, Yeung, Fanny G, Shah, Neel H, Wolf, Christian, Bonneau, Richard, Kirshenbaum, Kent
Format: Article
Language:English
Subjects:
Chromatography, High Pressure Liquid
Circular Dichroism
Crystallography, X-Ray
Dimerization
Magnetic Resonance Spectroscopy
Models, Molecular
Peptoids - chemistry
Protein Conformation
Rotation
Stereoisomerism
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja2028684