Toxicity of Aromatic Ketone to Yeast Cell and Improvement of the Asymmetric Reduction of Aromatic Ketone Catalyzed by Yeast Cell with the Introduction of Resin Adsorption
Zhong-Hua Yang1*, Rong Zeng2, Xu Chang1, Xuan-Ke Li1 and Guang-Hui Wang1
1College of Chemical Engineering and Technology, Wuhan University of Science and Technology, CN-430081 Wuhan, PR China
2College of Chemistry and Chemical Engineering, Hubei University, CN-430062 Wuhan, PR China
Article history:
Received November 7, 2006
Accepted October 12, 2007
Key words:
asymmetric reduction, chiral alcohol, acetophenone, S-α-phenylethyl alcohol, resin adsorption
Summary:
Asymmetric reduction of the prochiral aromatic ketone catalyzed by yeast cells is one of the most promising routes to produce its corresponding enantiopure aromatic alcohol, but the space-time yield does not meet people’s expectations. Therefore, the toxicity of aromatic ketone and aromatic alcohol to the yeast cell is investigated in this work. It has been found that the aromatic compounds are poisonous to the yeast cell. The activity of yeast cell decreases steeply when the concentration of acetophenone (ACP) is higher than 30.0 mmol/L. Asymmetric reduction of acetophenone to chiral S-α-phenylethyl alcohol (PEA) catalyzed by the yeast cell was chosen as the model reaction to study in detail the promotion effect of the introduction of the resin adsorption on the asymmetric reduction reaction. The resin acts as the substrate reservoir and product extraction agent in situ. It has been shown that this reaction could be remarkably improved with this technique when the appropriate kind of resin is applied. The enantioselectivity and yield are acceptable even though the initial ACP concentration reaches 72.2 mmol/L.
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