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Rieske Non-Heme Iron Dioxygenases: Applications and Future Perspectives

  • Fatma Feyza Özgen
  • Sandy SchmidtEmail author
Chapter

Abstract

The stereo- and regioselective oxidative functionalization of olefins is amongst the most challenging reactions in organic syntheses. In particular, the catalytic asymmetric dihydroxylation of alkenes has attracted considerable attention due to the facile further transformation of the chiral diol products into valuable derivatives, making them important building blocks for the pharmaceutical and chemical industry. Nature’s creativity in developing solutions for C–H-bond functionalization reactions like hydroxylations at activated or non-activated C–H-bonds is remarkably shown by an impressive list of metal-dependent enzymes. These enzymes, like the Rieske non-heme iron oxygenases (ROs) are able to activate molecular oxygen in order to generate reactive oxygen species capable of hydroxylating alkyl-substrates and they also promote further oxidative transformations. For many of these reactions no ‘classical’ chemical counterpart is known. ROs represent promising biocatalysts for these reactions since they are the only enzymes known to catalyze the stereoselective formation of vicinal cis-diols in one step. They are soluble multicomponent systems that harness the reductive power of NAD(P)H for oxygen activation. Due to their versatility, ROs are considered as the non-heme analogues of cytochrome P450 monooxygenases and, in addition to their relaxed substrate specificity, these enzymes can also catalyze various oxidation reactions, resulting in an enormous potential of these enzymes for manifold synthetically useful transformations. This chapter describes the current understanding of the structural determinants and the catalytic behavior of dioxygenase-catalyzed reactions, and highlights how in several cases this knowledge has been harnessed to design tailored catalysts for the synthesis of various natural products, polyfunctionalized metabolites and pharmaceutical intermediates. Moreover, the chapter also gives insights into recently characterized ROs catalyzing unusual reactions as well as applications in chemo-enzymatic cascade reactions for natural product synthesis.

Keywords

Rieske non-heme iron dioxygenases Ferredoxin Reductase Hydroxylation Dihydroxylation cis-Diols Natural product synthesis Chemo-enzymatic cascades 

Notes

Acknowledgements

This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 764920.

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© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Institute of Molecular BiotechnologyGraz University of TechnologyGrazAustria

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