Cooperative 5- and 10-membered ring interactions in the 10-helix folding of oxetin homo-oligomers

Homo-oligomers of the natural product oxetin ( cis -3-amino-2-oxetanecarboxylic acid) were prepared and their conformational behaviour studied in solution and solid state and by molecular modelling. The predominant secondary structure was a 10-helix, propiciously stabilized by a network of 5-membere...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-02, Vol.54 (16), p.1968-1971
Main Authors: Ragab, Sherif S, Kassir, Ahmad F, Guillot, Régis, Scherrmann, Marie-Christine, Boddaert, Thomas, Aitken, David J
Format: Article
Language:English
Subjects:
Chemical bonds
Hydrogen atoms
Molecular structure
Oligomers
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Summary:Homo-oligomers of the natural product oxetin ( cis -3-amino-2-oxetanecarboxylic acid) were prepared and their conformational behaviour studied in solution and solid state and by molecular modelling. The predominant secondary structure was a 10-helix, propiciously stabilized by a network of 5-membered ring H-bonds implicating ring oxygens and neighboring amide hydrogen atoms. A 10-helix conformer is stabilized by a parallel network of 5-membered ring interactions, providing a foldamer architecture featuring a series of bifurcated 5-ring/10-ring H-bonds.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc09964a