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One-Pot Biocatalytic Double Oxidation of α-Isophorone for the Synthesis of Ketoisophorone.
- Source :
- ChemCatChem; 9/8/2017, Vol. 9 Issue 17, p3338-3348, 11p
- Publication Year :
- 2017
-
Abstract
- The chemical synthesis of ketoisophorone, a valuable building block of vitamins and pharmaceuticals, suffers from several drawbacks in terms of reaction conditions and selectivity. Herein, the first biocatalytic one-pot double oxidation of the readily available α-isophorone to ketoisophorone is described. Variants of the self-sufficient P450cam-RhFRed with improved activity have been identified to perform the first step of the designed cascade (regio- and enantioselective allylic oxidation of α-isophorone to 4-hydroxy-α-isophorone). For the second step, the screening of a broad panel of alcohol dehydrogenases (ADHs) led to the identification of Cm-ADH10 from Candida magnoliae. The crystal structure of Cm-ADH10 was solved and docking experiments confirmed the preferred position and geometry of the substrate for catalysis. The synthesis of ketoisophorone was demonstrated both as a one-pot two-step process and as a cascade process employing designer cells co-expressing the two biocatalysts, with a productivity of up to 1.4 g L<superscript>−1</superscript> d<superscript>−1</superscript>. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 18673880
- Volume :
- 9
- Issue :
- 17
- Database :
- Complementary Index
- Journal :
- ChemCatChem
- Publication Type :
- Academic Journal
- Accession number :
- 125070850
- Full Text :
- https://doi.org/10.1002/cctc.201700620