Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase
Authors: | Matthias Kinne, Rene Ullrich, Kenneth E. Hammel, Katrin Scheibner, Martin Hofrichter |
Year: | 2008 |
Type: | Miscellaneous Publication |
Station: | Forest Products Laboratory |
Source: | Tetrahedron letters. Vol. 49, no. 41 (Oct. 6, 2008): pages 5950-5953. |
Abstract
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.