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Asymmetric Synthesis of (S)-2-octanol Catalyzed by Saccharomyces Cerevisiae

Author: LiYongNing
Tutor: GuoYangHao
School: Fuzhou University
Course: Biochemistry and Molecular Biology
Keywords: Saccharomyces cerevisiae (S)-2-octanol asymmetric synthesis
CLC: Q814
Type: Master's thesis
Year: 2006
Downloads: 151
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Abstract


(S)-2-octanol can be used as building block for the synthesis of FLCD（ferroelectricLCDs） and several optically active pharmaceutical intermediates. The reduction of 2-octanone or the resolution of （R,S）-2-octanol catalyzed by enzyme have been used for the synthesis of （S）-2-octanol. In this study the asymmetric reduction of 2-octanone to （S）-2-octanol catalyzed by FD-12 was studied.FD-12（Saccharomyces cerevisiae） was screened from different strains of Saccharomyces cerevisiae, which showed a high bioreduction activity and enantioselectivity. The product of asymmetric reduction was mainly （S）-2-octanol.FD-12’characteristic of the bioreduction was studied. The solubility of 2-octanone and 2-octanol in the aqueous phase was very low, with the value being 2.01 mmol·L-1 and 3.03 mmol·L-1 in the Tris-HCl buffer（32℃）. The high concentrations of 2-octanone and 2-octanol showed a toxic damage to Yeast FD-12. The bioreduction activity of FD-12 was inhibited at the higher concentration of 2-octanone(>15 mmol·L-1). At optimal conditions, pH8.0, 32℃, 16% inoculation, initial glucose concentration of 10g·L-1 and initial substrate of 10mmol·L-1 ,the yield of 2-octanol and the ee（S） value reached 92.23% and 78.80% respectively after 96h reaction.Through parameter estimation with least squares fit method and Quasi-Newton algorithm, the model proposed can be fitted to the experimental data well.μpm was 0.0346 mmol·h-1·g-1 dcw and the optimal concentration was 14.25mmol·L-1.The influence of three kinds of surfactant on the reduction of 2-octanone by FD-12 was studied. The solubility of 2-octanone in aqueous phase was improved greatly in the presence of SDS、OP and CTAB. An increase of yield and ee（S） could be obtained with a concentration of 0.2mmol·L-1SDS and OP. But the inhibition of the high concentration substrate would not be weakened.The water/organic solvent biphasic system was employed to the reduction of 2-octanone. Yeast possessed the best tolerance in the water/n-dodecane biphasic system than in the other 5 biphasic systems assayed. The metabolic activity retention and livability were as high as 90% in the water/n-dodecane. Under the optimal conditions in water/n-dodecane biphasic system, Vaq/Vorg 20/5, pH8.0, 32℃, a yield of 45.65% and an ee（S） value of 90.23% could be obtained when the co-substrate 10g·L-1 glucose and substrate 2-octanone of 50mmol·L-1 were used after 96h reaction. A yield of 46.11% and an ee（S） value of 95.72% were obtained with

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