Journal
PROCESS BIOCHEMISTRY
Volume 47, Issue 7, Pages 1037-1041Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.procbio.2012.01.014
Keywords
Enzymatic desymmetrization; Novozym 435; Co-solvent; Enantioselectivity; Methyl (R)-3-(4-fluorophenyl)glutarate
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Funding
- Key Project of National Natural Science Foundation of China [20936002]
- National Natural Science Foundation of China for Young Scholars [20906049]
- National Basic Research Program of China [2011CB710800]
- Hi-Tech Research and Development Program of China [2011AA02A209]
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An efficient procedure for enzymatic desymmetrization of the prochiral dimethyl 3-(4-fluorophenyl)glutarate (3-DFG) in an aqueous-organic phase was successfully developed to prepare methyl (R)-3-(4-fluorophenyl)glutarate ((R)-3-MFG). Novozym 435 was selected as a highly efficient biocatalyst through lipase screening. The effects of various parameters in terms of co-solvent and its concentration, buffer pH, ionic strength and reaction temperature, on the reaction were investigated. It was found that 0.2 M phosphate buffer (pH 8.0) containing 20% MTBE (v/v) was the optimum reaction medium, and the optimum reaction temperature was 30 degrees C. Under the optimized reaction conditions. (R)-3-MFG was obtained in 95.6% ee value and 92.6% yield after 64 h when the concentration of 3-DFG and Novozym 435 were 200 mmol/l and 20 g/l respectively. Furthermore. Novozym 435 showed an excellent operational stability, retaining above 95% of the initial activity and enantioselectivity after 10 cycles of reaction. The developed method has a potential to be used for efficient enzymatic production of (R)-3-MFG. (c) 2012 Elsevier Ltd. All rights reserved.
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