Chloroperoxidase‐Catalyzed Achmatowicz Rearrangements

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Volume Title
A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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Date
2018-06-07
Major/Subject
Mcode
Degree programme
Language
en
Pages
9
2717-2725
Series
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Volume 20
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.
Description
HUOM! TÄMÄ MANUSKA ON TILASSA CLOSED KUNNES ARTIKKELI ON JULKAISTU JA JULKAISUVIIVE MÄÄRITELTY KUSTANTAJAN JULKAISUPÄIVÄSTÄ ALKAEN. The manuscript is "closed" until the article has been published and the embargo date can be defined.
Keywords
enzyme catalysis, peroxidases, ring expansion, heterocycles, furan
Other note
Citation
Thiel , D , Blume , F , Jäger , C & Deska , J 2018 , ' Chloroperoxidase‐Catalyzed Achmatowicz Rearrangements ' , European Journal of Organic Chemistry , vol. 20 , pp. 2717-2725 . https://doi.org/10.1002/ejoc.201800333