Organic Solvent Tolerance of Retro-Friedel–Crafts Hydrolases
Retro-Friedel–Crafts hydrolases are co-factor independent enzymes with unusual reactivity and selectivity. These unique hydrolases are scarcely studied for biocatalytical applications in organic chemistry yet, although many other hydrolytic enzymes (e.g. lipases) are commonly applied as catalysts. Two Friedel–Crafts hydrolases were selected, namely 2,6-diacetylphloroglucinol hydrolase (PhlG) from Pseudomonas fluorescens and phloretin hydrolase from Eubacterium ramulus (Phy), to test the suitability of these enzymes in synthetic applications. The activity and stability of PhlG and Phy as lyophilized cells or lyophilized crude extracts were investigated in the presence of organic co-solvents. It was shown, that by careful selection of the co-solvent the enzymes catalyse C–C hydrolysis in a buffer solvent mixture with improved conversions at 50 mM substrate concentration. However, attempts to catalyze C–C-bond formation in organic solvents were unsuccessful.
KeywordsC–C hydrolase Enzyme stability Solvent tolerance Retro-Friedel–Crafts acylation
The research leading to these results has received funding from the European Union Seventh Framework Programme (FP7/2007-2013) under Grant Agreement No. FP7-PEOPLE-ITN-2008-238531.
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