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

The extracellular heme-thiolate peroxygenase of Agrocybe aegerita catalyzed the H 2O 2-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 y...

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Bibliographic Details
Published in:Tetrahedron letters 2008-10, Vol.49 (41), p.5950-5953
Main Authors: Kinne, Matthias, Ullrich, René, Hammel, Kenneth E., Scheibner, Katrin, Hofrichter, Martin
Format: Article
Language:English
Subjects:
2-(4-Hydroxyphenoxy)propionic acid
Agrocybe aegerita
Ascorbic acid
Cytochrome P450
Hydroxylation
Oxygenase
Peroxidase
Peroxygenase
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Summary:The extracellular heme-thiolate peroxygenase of Agrocybe aegerita catalyzed the H 2O 2-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 H 2O 2, 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.07.152