Novel folding patterns in a family of oligoanthranilamides: Non-peptide oligomers that form extended helical secondary structures

Yoshitomo Hamuro, Steven J. Geib, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

Anthranilamide derivatives are used as the basis for a series of novel oligomers that fold into helical secondary structures in the solid state. When combined with pyridine-2,6-dicarboxylic acid and 4,6-dimethoxy-1,3-diaminobenzene subunits, oligoanthranilamides can be induced to take up a coiled conformation corresponding to two turns of a helix. X-ray crystallography shows that intramolecular hydrogen bonding and π-π stacking interactions are important in stabilizing the extended helical structures. Furthermore, both experimental and calculated 1H NMR methods indicate that related conformations are taken up by the oligomers in chloroform solution.

Original languageEnglish (US)
Pages (from-to)10587-10593
Number of pages7
JournalJournal of the American Chemical Society
Volume119
Issue number44
DOIs
StatePublished - 1997

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X Ray Crystallography
Hydrogen Bonding
Chloroform
Oligomers
Conformations
X ray crystallography
Chlorine compounds
Pyridine
Hydrogen bonds
Nuclear magnetic resonance
Derivatives
Acids
3-phenylenediamine
dipicolinic acid
anthranilamide
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Novel folding patterns in a family of oligoanthranilamides : Non-peptide oligomers that form extended helical secondary structures. / Hamuro, Yoshitomo; Geib, Steven J.; Hamilton, Andrew.

In: Journal of the American Chemical Society, Vol. 119, No. 44, 1997, p. 10587-10593.

Research output: Contribution to journalArticle

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