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Issue 9, 2012
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Twice tied tight: Enforcing conformational order in bicyclic peptoid oligomers

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Abstract

Head-to-tail cyclization of N-substituted glycine peptoid oligomers is known to enforce their conformational ordering. We now describe the installation of an additional covalent constraint by bridging the side chains of a peptoid octamer macrocycle via Cu(I)-catalyzed azide–alkyne cycloaddition. Under dilute conditions, intramolecular side chain tethering is favored over formation of intermolecular crosslinked macrocycles. Both the bicyclic octamer and the hexadecamer intermolecular reaction product are characterized by crystallographic studies, providing X-ray diffraction structures of the largest peptoid compounds to date.

Graphical abstract: Twice tied tight: Enforcing conformational order in bicyclic peptoid oligomers

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Supplementary files

Article information


Submitted
18 Apr 2012
Accepted
31 May 2012
First published
18 Jun 2012

Chem. Sci., 2012,3, 2726-2731
Article type
Edge Article

Twice tied tight: Enforcing conformational order in bicyclic peptoid oligomers

S. B. L. Vollrath, S. Bräse and K. Kirshenbaum, Chem. Sci., 2012, 3, 2726 DOI: 10.1039/C2SC20473H

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