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Catalytic teamwork transforms alkenes selectively

Photocatalyst pairs with ene-reductase enzyme to obtain one enantiomer in reductions of mixtures

by Carmen Drahl
August 18, 2018 | A version of this story appeared in Volume 96, Issue 33


A reaction scheme depicts the reduction of an alkene to a specific alkane isomer, mediated by a photocatalyst-enzyme pair.

Double-bond-forming reactions commonly yield a mixture of alkene isomers with different geometric arrangements of functional groups. Subsequent transformations, such as reducing the double bond to a single bond, lead to mixtures that can be difficult to separate. John F. Hartwig of the University of California, Berkeley; Huimin Zhao of the University of Illinois, Urbana-Champaign; and their colleagues think strategic pairing can solve that problem and others. Catalyst pairs—both in biology and in industrial contexts—can carry out higher-yielding and more-selective reactions than can the individual catalysts in sequence. The team paired enzymes called ene-reductases with photocatalysts, which tend to be biocompatible because they often generate catalyst intermediates that are stable in water. The photocatalyst interconverts the two alkene isomers, and the awaiting enzyme selectively reduces one of the two isomers to a chiral product (Nature 2018, DOI: 10.1038/s41586-018-0413-7). The combination process also reduces single alkene isomers that would not react with the enzyme on its own (example shown). The team has filed a provisional patent application on the technology. A commentary accompanying the report notes that so far, the reaction requires substrates with aromatic groups, and the substrate concentrations are lower than industrial processes require.


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