Peptoid atropisomers |
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Authors: | Paul Bishwajit Butterfoss Glenn L Boswell Mikki G Renfrew P Douglas Yeung Fanny G Shah Neel H Wolf Christian Bonneau Richard Kirshenbaum Kent |
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Affiliation: | Department of Chemistry, New York University, New York, New York 10003, USA. |
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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. |
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