Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp. CCTCC M209061

Xiao, Zijun; Zong, Min‐Hua; Lou, Wen‐Yong

doi:10.1016/j.biortech.2009.06.006

Cited by 20 publications

(20 citation statements)

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“…CCTCC M209061, it was possible that the change in culture conditions might affect the rate of reduction of different substrates to different extents. The cells cultured in the improved medium were therefore tested as the biocatalyst for the key enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to ( R ) - 4-(trimethylsilyl)-3-butyn-2-ol that we investigated previously [10]. Compared with the previous work, using cells prepared from the optimized reaction medium, under the reduction reaction conditions described previously, the initial reaction rate increased from 0.5 μ mol/min to 1.13 μ mol/min; the yield was enhanced from 71% to 83% and the product e.e .…”

Section: Resultsmentioning

confidence: 99%

“…A novel strain, Acetobacter sp. CCTCC M209061, reported in our previous paper [10], isolated from Chinese kefir grains, showed exclusive anti-Prelog stereoselectivity for the reduction of 4-(trimethylsilyl)-3-butyn-2-one to ( R )-4-(trimethylsilyl)-3-butyn-2-ol, which is a key chiral intermediate for the synthesis of ( R )-benzyl-4-hydroxyl-2-pentynoate, a molecule that has potential therapeutic function for Alzheimer's disease. Also, Acetobacter sp.…”

Section: Introductionmentioning

confidence: 99%

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Optimization of culture conditions to produce high yields of active Acetobactersp. CCTCC M209061 cells for anti-Prelog reduction of prochiral ketones

et al. 2011

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BackgroundChiral alcohols are widely used in the synthesis of chiral pharmaceuticals, flavors and functional materials and appropriate whole-cell biocatalysts offer a highly enantioselective, minimally polluting route to these valuable compounds. The recently isolated strain Acetobacter sp. CCTCC M209061 showed exclusive anti-Prelog stereoselectivity for the reduction of prochiral ketones, but the low biomass has limited its commercialization and industrial applications. To tackle this problem, the effects of medium components and culture conditions on the strain's growth and reduction activity were explored.ResultsBy using a one-at-a-time method and a central composite rotatable design (CCRD), the optimal medium and culture conditions were found to be as follows: glucose 8.26 g/L, fructose 2.50 g/L, soy peptone 83.92 g/L, MnSO4·H2O 0.088 g/L, pH 5.70, 30°C and 10% (v/v) inoculum. Under the above-mentioned conditions, the biomass after 30 h cultivation reached 1.10 ± 0.03 g/L, which was 9.5-fold higher than that obtained with basic medium. Also, the reduction activity towards 4'-chloroacetophenone was markedly enhanced to 39.49 ± 0.96 μmol/min/g from 29.34 ± 0.65 μmol/min/g, with the product e.e. being above 99%. Comparable improvements were also seen with the enantioselective bioreduction of 4-(trimethylsilyl)-3-butyn-2-one to the key pharmaceutical precursor (R) - 4-(trimethylsilyl)-3-butyn-2-ol.ConclusionsThe biomass and reduction activity of Acetobacter sp. CCTCC M209061 can be greatly enhanced through the optimization strategy. This facilitates use of the strain in the anti-Prelog stereoselective reduction of prochiral ketones to enantiopure chiral alcohols as building blocks for many industries.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Optimization of culture conditions to produce high yields of active Acetobactersp. CCTCC M209061 cells for anti-Prelog reduction of prochiral ketones

et al. 2011

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“…A variety of microorganisms have been reported to be efficient in catalyzing prochrial ketones to enantiomerically pure chrial alcohols [16,25-29]. Therefore, several commercial available microorganisms ( Acetobacter pasteurianus GIM1.158, Acetobacter sp.…”

Section: Resultsmentioning

confidence: 99%

“…However, to our best knowledge, the use of Acetobacter sp . as a biocatalyst for the asymmetric reduction of prochiral ketones remains unexplored, with only few accounts published by us [16,20,23,24]. In these cases, a new acetic acid bacterium, Acetobacter sp.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic anti-Prelog reduction of prochiral ketones with whole cells of Acetobacter pasteurianus GIM1.158

Wei

Lou

et al. 2014

Microb Cell Fact

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BackgroundEnantiomerically pure alcohols are important building blocks for production of chiral pharmaceuticals, flavors, agrochemicals and functional materials and appropriate whole-cell biocatalysts offer a highly enantioselective, minimally polluting route to these valuable compounds. At present, most of these biocatalysts follow Prelog’s rule, and thus the (S)-alcohols are usually obtained when the smaller substituent of the ketone has the lower CIP priority. Only a few anti-Prelog (R)-specific whole cell biocatalysts have been reported. In this paper, the biocatalytic anti-Prelog reduction of 2-octanone to (R)-2-octanol was successfully conducted with high enantioselectivity using whole cells of Acetobacter pasteurianus GIM1.158.ResultsCompared with other microorganisms investigated, Acetobacter pasteurianus GIM1.158 was shown to be more effective for the reduction reaction, affording much higher yield, product enantiomeric excess (e.e.) and initial reaction rate. The optimal temperature, buffer pH, co-substrate and its concentration, substrate concentration, cell concentration and shaking rate were 35°C, 5.0, 500 mmol/L isopropanol, 40 mmol/L, 25 mg/mL and 120 r/min, respectively. Under the optimized conditions, the maximum yield and the product e.e. were 89.5% and >99.9%, respectively, in 70 minutes. Compared with the best available data in aqueous system (yield of 55%), the yield of (R)-2-octanol was greatly increased. Additionally, the efficient whole-cell biocatalytic process was feasible on a 200-mL preparative scale and the chemical yield increased to 95.0% with the product e.e. being >99.9%. Moreover, Acetobacter pasteurianus GIM1.158 cells were proved to be capable of catalyzing the anti-Prelog bioreduction of other prochiral carbonyl compounds with high efficiency.ConclusionsVia an effective increase in the maximum yield and the product e.e. with Acetobacter pasteurianus GIM1.158 cells, these results open the way to use of whole cells of this microorganism for challenging enantioselective reduction reactions on laboratory and commercial scales.

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“…ILs with an appropriate concentration can support a highly efficient whole-cell biocatalytic process. However, when concentrations of ILs in the reaction system are too high, they can retard the enzymatic activity and limit the mass transfer of substrate [26,27]. Therefore, the influence of [BPy]BF 4 concentration on the GDL biosynthesis of Y. lipolytica G3-3.21 was tested in this study.…”

Section: Optimization Of [Bpy]bf 4 Concentrationmentioning

confidence: 99%

Efficient biosynthesis of γ-decalactone in ionic liquids by immobilized whole cells of Yarrowia lipolytica G3-3.21 on attapulgite

Zhao

Jiang

2015

Bioprocess Biosyst Eng

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In this study, the biosynthesis of γ-decalactone (GDL) was successfully conducted in an ionic liquid (IL)-containing cosolvent system using immobilized cells of Yarrowia lipolytica G3-3.21 on attapulgite (ATG). We found the immobilized Y. lipolytica G3-3.21 cells in N-butyl-pyridinium tetrafluoroborate ([BPy]BF4) solution gave the highest activity of C16-Acyl-CoA oxidase and the maximum yield of GDL. The optimum immobilization conditions for the highest yield of GDL were 20 g/L of ATG, 1.5 % of CaCl2 and 2 % of sodium alginate (NaAlg). The optimal [BPy]BF4 content, buffer pH, reaction temperature, shaking speed, castor oil and glucose contents were 7.5 %, 26 °C, 150 rpm, 100 g/L and 10 %, respectively. Under the optimized conditions, the GDL yield was up to 8.05 g/L. After ten times of reuse, the GDL yield was 7.51 g/L, corresponding to 93.3 % of that obtained in the first batch, suggesting a good reusability and potential for industrial applications.

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Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp. CCTCC M209061

Cited by 20 publications

References 24 publications

Optimization of culture conditions to produce high yields of active Acetobactersp. CCTCC M209061 cells for anti-Prelog reduction of prochiral ketones

Optimization of culture conditions to produce high yields of active Acetobactersp. CCTCC M209061 cells for anti-Prelog reduction of prochiral ketones

Biocatalytic anti-Prelog reduction of prochiral ketones with whole cells of Acetobacter pasteurianus GIM1.158

Efficient biosynthesis of γ-decalactone in ionic liquids by immobilized whole cells of Yarrowia lipolytica G3-3.21 on attapulgite

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