Twice tied tight: Enforcing conformational order in bicyclic peptoid oligomers

Sidonie B L Vollrath, Stefan Bräse, Kent Kirshenbaum

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)2726-2731
Number of pages6
JournalChemical Science
Volume3
Issue number9
DOIs
StatePublished - Sep 2012

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Peptoids
Oligomers
N-substituted Glycines
Alkynes
Azides
Cycloaddition
Cyclization
Reaction products
X ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Twice tied tight : Enforcing conformational order in bicyclic peptoid oligomers. / Vollrath, Sidonie B L; Bräse, Stefan; Kirshenbaum, Kent.

In: Chemical Science, Vol. 3, No. 9, 09.2012, p. 2726-2731.

Research output: Contribution to journalArticle

Vollrath, Sidonie B L ; Bräse, Stefan ; Kirshenbaum, Kent. / Twice tied tight : Enforcing conformational order in bicyclic peptoid oligomers. In: Chemical Science. 2012 ; Vol. 3, No. 9. pp. 2726-2731.
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