Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond. (14th January 2016)

• Record Type: Journal Article
• Authors: Le Bailly, Bryden A. F.; Byrne, Liam; Clayden, Jonathan
• Is Part Of: Angewandte Chemie. Volume 128:Number 6(2016)
• Page Start: 2172
• Page End: 2176
• Publication Date: 2016-01-14
• Subjects: Foldamere -- Katalyse -- Konformation -- Peptide -- Photoschalter; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201510605
• Languages: English
• ISSNs: 0044-8249

Abstract

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.