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Asymmetric Conversion of 1-Phenyl-1,2-ethanediol by Candida parapsilosis SYB-1
全细胞近平滑假丝酵母(Candida parapsilosis)SYB–1不对称转化苯基乙二醇

Keywords: microbial stereoinversion,1-phenyl-1,2-ethanediol,screen,asymmetric conversion
微生物法
,苯基乙二醇,筛选,不对称转化

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Abstract:

Optically active 1-phenyl-1,2-ethanediol is an extremely valuable and versatile alcohol used as a chiral building block in organic synthesis. Among the microorganisms which are able to produce S-1-phenyl-1,2-ethanediol from the racemate by asymmetric conversion, Candida parapsilosis SYB-1 was selected as an candidate biocatalyst for the preparation of S-1-phenyl-1,2-ethanediol with the optical purity of 91% e.e. and the yield of 88%. It is found that the optimal conditions for biocatalytic conversion were 5% cells, 8?R,S-1-phenyl-1,2-ethanediol, pH 6.5, temperature 33oC and reaction time 48 h. Under such conditions, the optical purity of S-1-phenyl-1,2-ethanediol was improved from 91% e.e. to 99% e.e. By detecting the intermediate produced in the reaction by GC-MS, it was suggested that S-enantiomer was produced from the intermediate identified as b-hydroxyacetophenone by asymmetric reduction after stereoselective oxidation of R-enantiomer to b-hydroxyacetophenone.

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