Enzymatic aerobic ring rearrangement of optically active furylcarbinols.

Abstract:

:Biogenic furans are currently discussed as highly attractive alternative feedstock in a post-fossil society; thus, also the creation of sustainable furan valorization pathways appears of great importance. Here an artificial Achmatowicz monooxygenase activity for the aerobic ring expansion of furans is achieved by the combination of commercial glucose oxidase as oxygen-activating biocatalyst and wild-type chloroperoxidase as oxygen-transfer mediator, providing a biological ready-to-use solution for this truly synthetic furan rearrangement. In concert with enzymatic transformations for the enantioselective preparation of optically active furylcarbinols, purely biocatalytic reaction cascades for the stereocontrolled construction of complex pyranones are obtained, exhibiting high functional group tolerance even to oxidation-sensitive moieties.

journal_name

Nat Commun

journal_title

Nature communications

authors

Thiel D,Doknić D,Deska J

doi

10.1038/ncomms6278

subject

Has Abstract

pub_date

2014-10-22 00:00:00

pages

5278

issn

2041-1723

pii

ncomms6278

journal_volume

5

pub_type

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