Forest Products Laboratory

Title: Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase

Author: Kinne, Matthias; Ullrich, Rene; Hammel, Kenneth E.; Scheibner, Katrin; Hofrichter, Martin

Date: 2008

Source: Tetrahedron letters. Vol. 49, no. 41 (Oct. 6, 2008): pages 5950-5953.

Description: 

The extracellular heme-thiolate peroxygenase of Agrocybe aegerita catalyzed the H₂O₂-dependent hydroxylation of 2-phenoxypropionic acid (POPA) to give the herbicide precursor 2-(4-hydroxyphenoxy)propionic acid (HPOPA). The reaction proceeded regioselectively with an isomeric purity near 98%, and yielded the desired R-isomer of HPOPA with an enantiomeric excess of 60%. ¹⁸O-labeling experiments showed that the phenolic hydroxyl in HPOPA originated from H₂O₂, which establishes that the reaction is mechanistically a peroxygenation. Our results raise the possibility that fungal peroxygenases may be useful for a variety of organic oxidations.

Keywords: Peroxidase, peroxygenase, oxygenase, cytochrome P450, hydroxylation, 2-(4-Hydroxyphenoxy)propionic acid, ascorbic acid, wood-decaying fungi, biodegradation, peroxidases, catalysis, oxidation, hydrogen peroxide, chemical reactions, enzymes, biotechnology, industrial applications, Basidiomycetes, Agrocybe aegerita, 2-phenoxypropionic acid, POPA

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Citation

Kinne, Matthias; Ullrich, Rene; Hammel, Kenneth E.; Scheibner, Katrin; Hofrichter, Martin  2008.  Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase.   Tetrahedron letters. Vol. 49, no. 41 (Oct. 6, 2008): pages 5950-5953. .