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- Title
Novel biosynthesis of ( R)-ethyl-3-hydroxyglutarate with ( R)-enantioselective hydrolysis of racemic ethyl 4-cyano-3-hydroxybutyate by Rhodococcus erythropolis.
- Authors
Hua-Ping Dong; Zhi-Qiang Liu; Yu-Guo Zheng; Shen, Yin-Chu
- Abstract
( R)-ethyl-3-hydroxyglutarate with highly optical purity (≥99%) can be used as a novel precursor for synthesis of chiral side chain of rosuvastatin. In this study, a novel synthesis route of ( R)-ethyl-3-hydroxyglutarate by whole microorganism cells from racemic ethyl 4-cyano-3-hydroxybutyate was created. A strain ZJB-0910 capable of transforming racemic β-hydroxy aliphatic nitrile was isolated by employing a screening method based on a colorimetric reaction of Co2+ ion with ammonia, and identified as Rhodococcus erythropolis based on its morphology, physiological tests, Biolog, and the 16S rDNA sequence. After cultivation in a sterilized medium with composition of 20 g glucose, 5 g yeast extract, 0.5 g KH2PO4, 0.5 g K2HPO4, 0.2 g MgSO4·7H2O per liter at 30°C and 150 rpm for 48 h, the whole cells of R. erythropolis ZJB-0910 were prepared as a catalyst in ( R)-enantioselective hydrolysis of racemic ethyl 4-cyano-3-hydroxybutyate for synthesis of ( R)-ethyl-3-hydroxyglutarate, without bearing hydrolase activity for the ester bond of ethyl 4-cyano-3-hydroxybutyate. Under the optimized biotransformation conditions of pH 7.5, 30°C, and 20 mM substrate concentration, ( R)-ethyl-3-hydroxyglutarate with 46.2% yield ( ee > 99%) was afforded, and its chemical structure was determined by ESI-MS, NMR, and IR. The apparent Michaelis constant Km and maximum rate Vmax for this biocatalytic reaction were 0.01 M and 85.6 μmol min−1 g−1, respectively.
- Subjects
RHODOCOCCUS; HYDROLYSIS; ENANTIOSELECTIVE catalysis; STATINS (Cardiovascular agents); ALIPHATIC compounds; NITRILES; MORPHOLOGY; HYDROLASES; CHEMICAL structure
- Publication
Applied Microbiology & Biotechnology, 2010, Vol 87, Issue 4, p1335
- ISSN
0175-7598
- Publication type
Article
- DOI
10.1007/s00253-010-2584-5