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Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond
Author(s) -
Le Bailly Bryden A. F.,
Byrne Liam,
Clayden Jonathan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510605
Subject(s) - foldamer , oligomer , hydrogen bond , chemistry , enantiomer , turn (biochemistry) , stereochemistry , crystallography , molecule , polymer chemistry , organic chemistry , biochemistry
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.