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Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond
Bryden A F Le Bailly1,2, Liam Byrne2, Jonathan Clayden3
1School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Abstract:
Small changes in the structure of a foldamer may lead to gross changes in conformational preference. We show that the simple insertion or deletion of a single hydrogen bond by changes in pH or by photochemical deprotection is sufficient to refold a helical oligomer, interconverting M and P screw-sense preference. As a consequence of the switch, information may be transmitted to a remote catalytic site, selectively directing the formation of either of two enantiomeric products by a reaction involving 1,22-remote intermolecular asymmetric induction.
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