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Issue 9, 2013
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Benzylic hydroxylation of aromatic compounds by P450 BM3

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Abstract

Cytochrome P450 BM3 monooxygenase from Bacillus megaterium and its variants are promising catalysts for organic synthesis. Aiming at the identification of variants for selective hydroxylation of functionalised aromatic compounds, the double mutant F87A L188C showed remarkably improved catalytic activity towards a set of tested toluene derivatives. The apparent catalytic efficiency of this variant towards the model substrate methyl 2-methoxy-3-methylbenzoate was 63.6 s−1 M−1, which is 535-fold higher compared to that of wild-type BM3. Furthermore, the double mutant selectively catalysed the benzylic hydroxylation of numerous toluene derivatives, especially in the presence of carbonyl- or carboxyl-functions that are directly attached to the aromatic ring. Preparative scale conversion resulted in efficient production of methyl 3-(hydroxymethyl)-2-methoxybenzoate (73% yield) which proved that F87A L188C is a suitable, efficient and sustainable catalyst for the introduction of benzylic hydroxyl groups in general.

Graphical abstract: Benzylic hydroxylation of aromatic compounds by P450 BM3

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Publication details

The article was received on 03 May 2013, accepted on 05 Jul 2013 and first published on 08 Jul 2013


Article type: Paper
DOI: 10.1039/C3GC40838H
Citation: Green Chem., 2013,15, 2408-2421
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    Benzylic hydroxylation of aromatic compounds by P450 BM3

    K. Neufeld, J. Marienhagen, U. Schwaneberg and J. Pietruszka, Green Chem., 2013, 15, 2408
    DOI: 10.1039/C3GC40838H

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