Chloroperoxidase‐Catalyzed Achmatowicz Rearrangements

Daniel Thiel, Fabian Blume, Christina Jäger, Jan Deska

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5 Citations (Scopus)
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Abstract

Chloroperoxidase from Caldariomyces fumago catalyzes the selective oxidation of furfuryl alcohols in an Achmatowicz‐type ring expansion. In combination with glucose oxidase as oxygen‐activating biocatalyst, a purely enzymatic, aerobic protocol for the synthesis of 6‐hydroxypyranone building blocks is obtained. Thanks to an only modest stereochemical bias of the oxygenating heme protein, optically active alcohols of either configuration are converted without a significant mismatch opening up opportunities for enantioselective multienzymatic cascades. Balancing the oxidase‐driven aerobic activation, extended enzyme half‐lives and productive conversion of poorly soluble and slowly reacting substrates can be achieved with high yields of the six‐membered O‐heterocycles.
Original languageEnglish
Pages (from-to)2717-2725
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume20
DOIs
Publication statusPublished - 7 Jun 2018
MoE publication typeA1 Journal article-refereed

Keywords

  • enzyme catalysis
  • peroxidases
  • ring expansion
  • heterocycles
  • furan

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    Beyond Biosynthesis: Enzymes as Catalysts in Non-natural Synthetic Transformations

    Blume, F., Jäger, C., Deska, J., Naapuri, J., Liu, Y., Kiefer, A. & Wagner, P.

    01/09/201631/03/2021

    Project: Academy of Finland: Other research funding

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