N-Naphthyl peptoid foldamers exhibiting atropisomerism

Bishwajit Paul; Glenn L Butterfoss; Mikki G Boswell; Mia L Huang; Richard Bonneau; Christian Wolf; Kent Kirshenbaum

doi:10.1021/ol203452f

N-Naphthyl peptoid foldamers exhibiting atropisomerism

Org Lett. 2012 Feb 3;14(3):926-9. doi: 10.1021/ol203452f. Epub 2012 Jan 24.

Authors

Bishwajit Paul¹, Glenn L Butterfoss, Mikki G Boswell, Mia L Huang, Richard Bonneau, Christian Wolf, Kent Kirshenbaum

Affiliation

¹ Department of Chemistry and Center for Genomics and Systems Biology, New York University, New York, New York 10003, USA.

PMID: 22272975
DOI: 10.1021/ol203452f

Abstract

We introduce peptoid oligomers incorporating N-(1)-naphthyl glycine monomers. Axial chirality was established due to restricted rotation about the C-N(aryl) bond. Atropisomerism of both linear and cyclic peptoids was investigated by computational analysis, dynamic HPLC, and X-ray crystallographic studies.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Models, Molecular
Peptoids / chemistry*
Protein Folding*
Stereoisomerism

Substances

Peptoids

Grants and funding

C06RR-165720/RR/NCRR NIH HHS/United States