Engineering Rieske Non-Heme Iron Oxygenases for the Asymmetric Dihydroxylation of Alkenes

Angewandte Chemie
Christine GallyBernhard Hauer

Abstract

The asymmetric dihydroxylation of olefins is of special interest due to the facile transformation of the chiral diol products into valuable derivatives. Rieske non-heme iron oxygenases (ROs) represent promising biocatalysts for this reaction as they can be engineered to efficiently catalyze the selective mono- and dihydroxylation of various olefins. The introduction of a single point mutation improved selectivities (≥95 %) and conversions (>99 %) towards selected alkenes. By modifying the size of one active site amino acid side chain, we were able to modulate the regio- and stereoselectivity of these enzymes. For distinct substrates, mutants displayed altered regioselectivities or even favored opposite enantiomers compared to the wild-type ROs, offering a sustainable approach for the oxyfunctionalization of a wide variety of structurally different olefins.

References

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Citations

Aug 17, 2016·Accounts of Chemical Research·Tillmann Heinisch, Thomas R Ward
Mar 2, 2018·Annual Review of Biochemistry·Cathleen Zeymer, Donald Hilvert
Apr 3, 2019·ChemSusChem·Roger A Sheldon, Dean Brady
Feb 23, 2019·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Wissam FarhatPer-Olof Syrén
Jan 14, 2021·Organic & Biomolecular Chemistry·Cristina Preston-HerreraJordan T Froese
Jan 15, 2021·Organic Letters·Yusuke ArakiToshio Nishikawa
Feb 19, 2021·Nature Communications·Peter M HeinemannBernhard Hauer

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