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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 language | English |
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Pages (from-to) | 2717-2725 |
Number of pages | 9 |
Journal | European Journal of Organic Chemistry |
Volume | 20 |
DOIs | |
Publication status | Published - 7 Jun 2018 |
MoE publication type | A1 Journal article-refereed |
Keywords
- enzyme catalysis
- peroxidases
- ring expansion
- heterocycles
- furan
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Dive into the research topics of 'Chloroperoxidase‐Catalyzed Achmatowicz Rearrangements'. Together they form a unique fingerprint.Projects
- 1 Finished
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Beyond Biosynthesis: Enzymes as Catalysts in Non-natural Synthetic Transformations
Deska, J., Naapuri, J., Liu, Y., Blume, F., Jäger, C. & Kiefer, A.
01/09/2016 → 31/03/2021
Project: Academy of Finland: Other research funding
Equipment
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Bioeconomy Research Infrastructure
Jukka Seppälä (Manager)
School of Chemical TechnologyFacility/equipment: Facility