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

Bryden A F Le Bailly; Liam Byrne; Jonathan Clayden

doi:10.1002/anie.201510605

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

Angew Chem Int Ed Engl. 2016 Feb 5;55(6):2132-6. doi: 10.1002/anie.201510605. Epub 2016 Jan 14.

Authors

Bryden A F Le Bailly^{1

2}, Liam Byrne², Jonathan Clayden³

Affiliations

¹ School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
² School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
³ School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. j.clayden@bristol.ac.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.

Keywords: biocatalysis; conformation; foldamers; peptides; photoswitches.

Publication types

Research Support, Non-U.S. Gov't