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.

Export metadata

Additional Services

Search Google Scholar
Metadaten
Author: Matthias Kinne, René UllrichORCiD, Kenneth E. Hammel, Katrin Scheibner, Martin HofrichterORCiD
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
Einverstanden ✔
Diese Webseite verwendet technisch erforderliche Session-Cookies. Durch die weitere Nutzung der Webseite stimmen Sie diesem zu. Unsere Datenschutzerklärung finden Sie hier.