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J Am Chem Soc. 2011 Jul 20;133(28):10910-9. doi: 10.1021/ja2028684. Epub 2011 Jun 22.

Peptoid atropisomers.

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  • 1Department of Chemistry, New York University, New York, New York 10003, USA.

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.

PMID:
21634437
DOI:
10.1021/ja2028684
[PubMed - indexed for MEDLINE]
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