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

Bryden A F Le Bailly, Liam Byrne, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalLetter (Academic Journal)

39 Citations (Scopus)
294 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)2132–2136
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number6
Early online date14 Jan 2016
DOIs
Publication statusPublished - 5 Feb 2016

Keywords

  • Biocatalysis
  • Conformation
  • Foldamers
  • Peptides
  • Photoswitches

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