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 inJournal of the American Chemical Society Vol. 133; no. 28; pp. 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 Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.07.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Chromatography, High Pressure Liquid
Circular Dichroism
Crystallography, X-Ray
Dimerization
Magnetic Resonance Spectroscopy
Models, Molecular
Peptoids - chemistry
Physical Sciences
Protein Conformation
Rotation
Science & Technology
Stereoisomerism
SIDE-CHAINS
ASYMMETRIC N-ARYLATION
AMINO-ACID
BIARYL ATROPISOMERS
SUBSTITUTED GLYCINES
SOLID-PHASE SYNTHESIS
AROMATIC AMIDES
AXIAL CHIRALITY
NONBIOLOGICAL POLYMER
SECONDARY STRUCTURE
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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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja2028684