This title appears in the Scientific Report :
2017
Please use the identifier:
http://dx.doi.org/10.1002/cbic.201600685 in citations.
P450 BM3-Catalyzed Regio- and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins
P450 BM3-Catalyzed Regio- and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins
Cytochrome P450 BM3 monooxygenases are able to catalyze the regio- and stereoselective oxygenation of a broad range of substrates, with promising potential for synthetic applications. To study the suitability of P450 BM3 variants for stereoselective benzylic hydroxylation of 2-alkylated benzoic acid...
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Personal Name(s): | Holec, Claudia |
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Hartrampf, Ute / Neufeld, Katharina / Pietruszka, Jörg (Corresponding author) | |
Contributing Institute: |
Biotechnologie; IBG-1 Institut für Bioorganische Chemie (HHUD); IBOC |
Published in: | ChemBioChem, 18 (2017) 7, S. 676 - 684 |
Imprint: |
Weinheim
Wiley-VCH
2017
|
PubMed ID: |
28107587 |
DOI: |
10.1002/cbic.201600685 |
Document Type: |
Journal Article |
Research Program: |
Innovative Synergisms |
Publikationsportal JuSER |
Cytochrome P450 BM3 monooxygenases are able to catalyze the regio- and stereoselective oxygenation of a broad range of substrates, with promising potential for synthetic applications. To study the suitability of P450 BM3 variants for stereoselective benzylic hydroxylation of 2-alkylated benzoic acid esters, the biotransformation of methyl 2-ethylbenzoate, resulting in both enantiomeric forms of 3-methylphthalide, was investigated. In the case of methyl 2-propylbenzoate as a substrate the regioselectivity of the reaction was shifted towards β-hydroxylation, resulting in the synthesis of enantioenriched R- and S-configured 3-methylisochroman-1-one. The potential of P450 BM3 variants for regio- and stereoselective synthesis of phthalides and isocoumarins offers a new route to a class of compounds that are valuable synthons for a variety of natural compounds. |