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

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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Letter (Academic Journal) › peer-review

67 Citations (Scopus)

431 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 language	English
Pages (from-to)	2132–2136
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	6
Early online date	14 Jan 2016
DOIs	https://doi.org/10.1002/anie.201510605
Publication status	Published - 5 Feb 2016

Research Groups and Themes

Organic & Biological

Keywords

Biocatalysis
Conformation
Foldamers
Peptides
Photoswitches

Access to Document

10.1002/anie.201510605

Bailly_et_al-2016-Angewandte_Chemie_International_Edition
This is the open access version of the following article: Le Bailly, BAF, Byrne, L & Clayden, J, 2015, ‘Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond’. Vol. 55, Iss. 6 of Angewandte Chemie International Edition (pp.2132-2136), which has been published in final form at DOI: 10.1002/anie.201510605.
Final published version, 2.14 MBLicence: CC BY

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AU - Byrne, Liam

AU - Clayden, Jonathan

PY - 2016/2/5

Y1 - 2016/2/5

N2 - 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.

AB - 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.

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KW - Conformation

KW - Foldamers

KW - Peptides

KW - Photoswitches

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DO - 10.1002/anie.201510605

M3 - Letter (Academic Journal)

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

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

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Professor Jonathan Clayden

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

Abstract

Research Groups and Themes

Keywords

Access to Document

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Professor Jonathan Clayden

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