Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 7, Pages 2870-2880Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405792
Keywords
foldamers; helical structures; thioureas; unfolding; X-ray diffraction
Categories
Funding
- CNRS
- University of Bordeaux (UB)
- Conseil Regional d'Aquitaine [20091102003]
- Agence Nationale de la Recherche [ANR-10-RPDOC-016, ANR-12-ASTR-0024]
- DGA
- Region Aquitaine
- ANR
- Agence Nationale de la Recherche (ANR) [ANR-12-ASTR-0024] Funding Source: Agence Nationale de la Recherche (ANR)
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Nearly isosteric oxo to thioxo substitution was employed to interrogate the structure of foldamers with a urea backbone and explore the relationship between helical folding and hydrogen-bonding interactions. A series of oligomers with urea bonds substituted by thiourea bonds at discrete or all positions in the sequence have been prepared and their folding propensity was studied by using a combination of spectroscopic methods and X-ray diffraction. The outcome of oxo to thioxo replacements on the helical folding was found to depend on whether central or terminal ureas were modified. The canonical helix geometry was not affected upon insertion of thioureas close to the negative end of the helix dipole, whereas thioureas close to the positive pole were found to increase the terminal flexibility and cause helix fraying. Perturbation was amplified when a selenourea was incorporated instead, leading to a structure that is only partly folded.
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