Dibenzazepinyl ureas as dual NMR and CD probes of helical screw-sense preference in conformationally equilibrating dynamic foldamers

Conformationally mobile oligomers with helical structures, or 'dynamic foldamers', may populate a mixture of screw-sense conformers whose relative proportion has been used as a means of communicating information on amolecular scale. The dibenzazepinyl urea provides a means of quantifying b...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 78; pp. 10768 - 10771
Main Authors Diemer, Vincent, Maury, Julien, Le Bailly, Bryden A. F., Webb, Simon J., Clayden, Jonathan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
L-AMINO-ACID
ALPHA-AMINO
CIRCULAR-DICHROISM
THERMODYNAMIC CONTROL
AXIAL CHIRALITY
ATROPISOMERIC AMIDES
INFORMATION
OLIGOPEPTIDES
ATOMIC-RESOLUTION
COMMUNICATION
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Summary:Conformationally mobile oligomers with helical structures, or 'dynamic foldamers', may populate a mixture of screw-sense conformers whose relative proportion has been used as a means of communicating information on amolecular scale. The dibenzazepinyl urea provides a means of quantifying both the sense and degree of this screw-sense preference through a combination of circular dichroism (CD) and NMR spectroscopy. The dibenzazepinyl urea probe is synthetically versatile, readily accessible, and easy to introduce to the terminus of an amide or a urea foldamer.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc06427f