Asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-1-phenylpropanol using immobilized Saccharomyces cerevisiae CGMCC 2266 cells

Yang, Gensheng; Ou, Zhimin; Yao, Shan‐Jing; Xu, Jiaxi

doi:10.1016/j.molcatb.2008.07.002

Cited by 13 publications

(9 citation statements)

References 27 publications

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“…In addition, low yields and low enantiomeric purities due to the different stereospecificities of the reductases present in a single cell have often limited its usage as a versatile biotransformation tool. Again, studies on the use of immobilized cells have been attempted to overcome this problem74, 116, while others have sought improvement using engineered recombinant strains and process design40, 57. Combining overexpression and knockout strategies would significantly enhance the levels of stereoselectivity of the baker's yeast93.…”

Section: Challenges and Opportunitiesmentioning

confidence: 99%

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Khor

Uzir

2010

Yeast

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Terpenes and terpenoids are among the key impact substances in the food and fragrance industries. Equipped with pharmacological properties and applications as ideal precursors for the biotechnological production of natural aroma chemicals, interests in these compounds have been escalating. Hence, the syntheses of new derivatives that can show improved properties are often called for. Stereoselective biotransformation offers several benefits to increase the rate of production, in terms of both the percentage yield and its enantiomeric excesses. Baker's yeast (Saccharomyces cerevisiae) is broadly used as a whole cell stereospecific reduction biocatalyst, due to its capability in reducing carbonyls and carbon-carbon double bonds, which also extends its functionality as a versatile biocatalyst in terpenoid biotransformation. This review provides some insights on the development and prospects in the reductive biotransformation of monoterpenoids and sesquiterpenoids using S. cerevisiae, with an overview of strategies to overcome the common challenges in large-scale implementation.

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Section: Challenges and Opportunitiesmentioning

confidence: 99%

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Khor

Uzir

2010

Yeast

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“…9,10 To our knowledge, few literatures have been reported about the bacterial whole cell-mediated reduction of CPE by now. Lately, a new bacterial strain, 5 Materials.…”

Section: Introductionmentioning

confidence: 99%

Enhancing Asymmetric Reduction of 3-Chloropropiophenone with Immobilized Acetobacter sp. CCTCC M209061 Cells by Using Deep Eutectic Solvents as Cosolvents

et al. 2015

ACS Sustainable Chem. Eng.

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Use of deep eutectic solvents (DESs) to improve biocatalytic asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-1-phenylpropanol catalyzed by whole-cell of Acetobacter sp. CCTCC M209061 was successfully performed. The cells immobilized on PVA-sodium sulfate exhibited markedly enhanced stability. Diverse DESs as co-solvents manifested significantly different influences on the reaction. Among them, the DES choline chloride/urea ([ChCl][U]) showed the best biocompatibility and moderately increased the cell member permeability, as demonstrated by MAR and flow cytometry assays, and consequently gave the best results. For the bioreduction conducted in the [ChCl][U]-containing system, the optimum [ChCl][U] content, substrate concentration, glucose concentration, pH and temperature were 5% (v/v), 10.0 mmol/L, 60 mmol/L, 5.5 and 30 °C, respectively. Under the optimized conditions, the obtained yield and product e.e. were 82.3% and above 99.0% at a reaction time of 6 h, respectively, and the productivity was 1.37 mmol/L/h. The efficient whole-cell biocatalytic process proved to be feasible on a 500-mL preparative scale. Moreover, the combination of water-immiscible ionic liquid C 4 MIM·PF 6 with [ChCl][U] in a biphasic system further enhanced substrate concentration (16.0 mmol/L), product yield (93.3%) and productivity (1.87 mmol/L/h) significantly, showing to be very promising for biocatalytic synthesis of (S)-3-chloro-1-phenylpropanol with immobilized Acetobacter sp. CCTCC M209061 cells.Acetobacter sp. CCTCC M209061, isolated from Chinese kefir grains by our group, was used as an efficient biocatalyst for highly enantioselective anti-Prelog reduction of prochiral ketones. 11Over the last several years, deep eutectic solvents (DESs) have been considered as another promising alternative to conventional ionic liquids (ILs) as green solvents. 12, 13 DESs are eutectic mixtures composed of two or three cheap and safe components which could associate with each other through hydrogen bond interactions. 14 These solvents not only share the similar characteristics with ILs such as low vapor pressure, non-flammability, thermal stability, but also have some special virtues including relatively low cost, good sustainability, biocompatibility and biodegradability. 15,16 Most importantly, the formation of these solvents is very simple and needs no further purification steps. Up to now, there appears to be some researches related to the applications of DESs as co-solvents in biocatalytic reactions, especially in enzyme-catalyzed reactions. [17][18][19] However, few accounts were published about whole-cell biocatalysis in a In the present study, we attempted for the first time to use various DESs as co-solvents in aqueous system to improve the biocatalytic asymmetric reduction of CPE with immobilized Acetobacter sp. CCTCC M209061 cells (Scheme 1). The biocompatibility of these DESs with the cells and their effects on the cell member integrity were investigated systematically as well as several influential factors on the react...

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“…to yield (S)-3-chloro-1-phenyl-propanol [356]. Similarly, propranolol and analogs have been accessed [357,358].…”

Section: Figure 2122mentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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Asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-1-phenylpropanol using immobilized Saccharomyces cerevisiae CGMCC 2266 cells

Cited by 13 publications

References 27 publications

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Enhancing Asymmetric Reduction of 3-Chloropropiophenone with Immobilized Acetobacter sp. CCTCC M209061 Cells by Using Deep Eutectic Solvents as Cosolvents

Yeast‐Mediated Stereoselective Synthesis

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