616895-65-9Relevant articles and documents
Chloroperoxidase-Catalyzed Achmatowicz Rearrangements
Thiel, Daniel,Blume, Fabian,J?ger, Christina,Deska, Jan
, p. 2717 - 2725 (2018)
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.