Twice tied tight: Enforcing conformational order in bicyclic peptoid oligomers

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 viaCu(i)-catalyzed azide-alkyne cycloaddition. Unde...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2012-01, Vol.3 (9), p.2726-2731
Main Authors: Vollrath, Sidonie BL, Braese, Stefan, Kirshenbaum, Kent
Format: Article
Language:English
Subjects:
Covalence
Crosslinking
Crystallography
Diffraction
Glycine
Oligomers
Tethering
X-rays
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Summary: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 viaCu(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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c2sc20473h