Work

Biocatalytic Conversion of Furans into Pyrrolinones Using a Class I Unspecific Peroxygenase

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide The biocatalytic conversion of furans and amines into 4-pyrrolin-2-ones can be achieved using the Class I Unspecific Peroxygenase artUPO. The reactions are broad in scope and typically operate in good yield, using a simple, easily scalable H 2 O 2 driven protocol, in which exogenous enzyme cofactors are not required. All of these biotransformations were performed on a preparative scale to deliver synthetically useful quantities of pyrrolinones. A cascade mechanism likely operates, in which UPO-mediated oxidative ring opening of the furan first delivers a reactive 1,4-dicarbonyl intermediate, followed by condensation with the added amine and rearrangement to the pyrrolinone product outside the UPO active site.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c05307

Authors: Benjamin Melling, Katy A. S. Cornish, Jared Cartwright, Nicholas P. Mulholland, William P. Unsworth, Gideon Grogan

Institutions: University of York, Syngenta (United Kingdom), Syngenta (France), Syngenta (Switzerland)

Language: English

Topic: Enzyme Catalysis and Immobilization

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Engineering and Physical Sciences Research Council