Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond.

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.

SUBMITTER: Le Bailly BA 

PROVIDER: S-EPMC4755161 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature