English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Paper

Switching between enantiomers by combining chromoselective photocatalysis and biocatalysis

MPS-Authors
/persons/resource/persons243163

Reischauer,  Susanne
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons205903

Pieber,  Bartholomäus
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

External Ressource
No external resources are shared
Fulltext (public)

Preprint.pdf
(Any fulltext), 356KB

Supplementary Material (public)
There is no public supplementary material available
Citation

Schmermund, L., Reischauer, S., Bierbaumer, S., Winkler, C., Diaz-Rodriguez, A., Edwards, L. J., et al. (2021). Switching between enantiomers by combining chromoselective photocatalysis and biocatalysis. ChemRxiv, 13521527. doi:10.26434/chemrxiv.13521527.v1.


Cite as: http://hdl.handle.net/21.11116/0000-0007-ABBC-5
Abstract
Controlling the selectivity of a chemical reaction with external stimuli is common in thermal processes, but rare in visible‐light photocatalysis. Here we show that the redox potential of a carbon nitride photocatalyst (CN‐OA‐m) can be tuned by changing the irradiation wavelength to generate electron holes with different oxidation potentials. This tuning was the key to realizing photo‐chemo‐enzymatic cascades that give either the (S)‐ or the (R)‐enantiomer of phenylethanol. In combination with an unspecific peroxygenase from Agrocybe aegerita, green light irradiation of CN‐OA‐m led to the enantioselective hydroxylation of ethylbenzene to (R)‐1‐phenylethanol (99% ee). In contrast, blue light irradiation triggered the photocatalytic oxidation of ethylbenzene to acetophenone, which in turn was enantioselectively reduced with an alcohol dehydrogenase from Rhodococcus ruber to form(S)‐1‐phenylethanol (93% ee).