催化学报

催化学报 ›› 2009, Vol. 30 ›› Issue (4): 370-374.

• 研究论文 • 上一篇    

Efficient Synthesis of (S)-1-(2-chlorophenyl)ethanol in the Submerged Culture of Alternaria alternata Isolate

Esabi B. KURBANOGLU1,*, Mesut TASKIN1, Kani ZILBEYAZ2, Ismet HASENEKOGLU3   

  1. 1Department of Biology, Faculty of Arts and Sciences, Ataturk University, Erzurum, Turkey; 2Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, Erzurum, Turkey
  • 收稿日期:2009-04-25 出版日期:2009-04-25 发布日期:2013-01-21

Efficient Synthesis of (S)-1-(2-chlorophenyl)ethanol in the Submerged Culture of Alternaria alternata Isolate

Esabi B. KURBANOGLU1,*, Mesut TASKIN1, Kani ZILBEYAZ2, Ismet HASENEKOGLU3   

  1. 1Department of Biology, Faculty of Arts and Sciences, Ataturk University, Erzurum, Turkey; 2Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, Erzurum, Turkey
  • Received:2009-04-25 Online:2009-04-25 Published:2013-01-21

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摘要： (S)-1-(2-chlorophenyl)ethanol is a key intermediate of L-cloprenaline used for relieving asthma symptoms. The asymmetric reduction of 2-chloroacetophenone 1 to (S)-1-(2-chlorophenyl)ethanol 2 in the submerged culture of Alternaria alternata isolates was studied. A. alternata EBK-8 isolate was the most effective biocatalyst. The bioactivity of the fungus could be significantly improved by the optimization of culture conditions. Parameters such as pH, temperature, agitation, and incubation time considerably influenced the substrate conversion and the optical purity of the product. The reaction was carried out in a culture medium at a substrate concentration of 30 mmol/L and produced the desired product with high conversion (100%) and isolated yield (80%) with an excellent enantiomeric excess (ee) of >99%. Under the optimum conditions, after 54 h reaction time, 24 mmol/L 2 from 30 mmol/L 1 could be produced. As a result, the submerged fer-mentation of A. alternata EBK-8 was found to be suitable for the asymmetric reduction of 1 to 2.

关键词: Alternaria alternata, bioconversion, biocatalysis, 2-chloroacetophenone, fermentation, optimization

Abstract: The asymmetric reduction of 2-chloroacetophenone to (S)-1-(2-chlorophenyl)ethanol in the batch culture of Alternaria alternata has been studied on a laboratory scale. The reaction has been carried out in a culture medium at a substrate concentration of 30 mmol/L and produced the desired product with complete conversion and an excellent enantiomeric excess of >99%. The yield of the process was calculated as 80%.

Key words: Alternaria alternata, bioconversion, biocatalysis, 2-chloroacetophenone, fermentation, optimization