Regioselective preparation of (R)-2-(4-Hydroxyphenoxy)propionic acid with a fungal peroxygenase
- 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.
Author: | Matthias Kinne, René UllrichORCiD, Kenneth E. Hammel, Katrin Scheibner, Martin HofrichterORCiD |
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URL: | http://www.sciencedirect.com/science/article/pii/S0040403908014421 |
DOI: | https://doi.org/10.1016/j.tetlet.2008.07.152 |
ISSN: | 1873-3581 |
Title of the source (English): | Tetrahedron Letters |
Document Type: | Scientific journal article peer-reviewed |
Language: | English |
Year of publication: | 2008 |
Tag: | 2-(4-Hydroxyphenoxy)propionic acid; Ascorbic acid; Cytochrome P450; Hydroxylation; Oxygenase; Peroxidase; Peroxygenase |
Volume/Year: | 49 |
Issue number: | 41 |
First Page: | 5950 |
Last Page: | 5953 |
Faculty/Chair: | Fakultät 2 Umwelt und Naturwissenschaften / FG Enzymtechnologie |
Institution name at the time of publication: | Fakultät für Naturwissenschaften (eHL) / Prof. Enzymtechnologie |