Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 6, Pages 2132-2136Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510605
Keywords
biocatalysis; conformation; foldamers; peptides; photoswitches
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Funding
- ERC (Advanced Investigator Grant ROCOCO)
- EPSRC [EP/K039547/1, EP/L018527/1]
- Engineering and Physical Sciences Research Council [EP/L018527/1, EP/K039547/1, EP/L019728/1] Funding Source: researchfish
- EPSRC [EP/K039547/1, EP/L019728/1] Funding Source: UKRI
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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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