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

doi:10.1021/ja2028684

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 journal › Article › peer-review

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 language	English (US)
Pages (from-to)	10910-10919
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	133
Issue number	28
DOIs	https://doi.org/10.1021/ja2028684
State	Published - Jul 20 2011

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja2028684

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title = "Peptoid atropisomers",

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.",

author = "Bishwajit Paul and Butterfoss, {Glenn L.} and Boswell, {Mikki G.} and Renfrew, {P. Douglas} and Yeung, {Fanny G.} and Shah, {Neel H.} and Christian Wolf and Richard Bonneau and Kent Kirshenbaum",

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AU - Paul, Bishwajit

AU - Butterfoss, Glenn L.

AU - Boswell, Mikki G.

AU - Renfrew, P. Douglas

AU - Yeung, Fanny G.

AU - Shah, Neel H.

AU - Wolf, Christian

AU - Bonneau, Richard

AU - Kirshenbaum, Kent

PY - 2011/7/20

Y1 - 2011/7/20

N2 - 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.

AB - 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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Peptoid atropisomers

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ASJC Scopus subject areas

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