Şahin Engin, Dertli Enes
Department of Food Engineering, Faculty of Engineering, Bayburt University, Bayburt, 69000, Turkey.
Chem Biodivers. 2017 Sep;14(9). doi: 10.1002/cbdv.201700121. Epub 2017 Sep 2.
The increasing demand for biocatalysts in synthesizing enantiomerically pure chiral alcohols results from the outstanding characteristics of biocatalysts in reaction, economic, and ecological issues. Herein, fifteen yeast strains belonging to three food originated yeast species Candida zeylanoides, Pichia fermentans, and Saccharomyces uvarum were tested for their capability for asymmetric reduction of acetophenone to 1-phenylethanol as biocatalysts. Of these strains, C. zeylanoides P1 showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high yields. The preparative scale asymmetric bioreduction of 4-nitroacetophenone (1m) by C. zeylanoides P1 gave (S)-1-(4-nitrophenyl)ethanol (2m) with 89% yield and > 99% enantiomeric excess. Compound 2m has been obtained in an enantiomerically pure and inexpensive form. Additionally, these results indicate that C. zeylanoides P1 is a promising biocatalyst for the synthesis of chiral alcohols in industry.
在合成对映体纯的手性醇中对生物催化剂需求的不断增加，源于生物催化剂在反应、经济和生态问题方面的突出特性。在此，测试了属于三种食品源酵母物种——季也蒙毕赤酵母、发酵毕赤酵母和葡萄汁酵母的15株酵母菌株作为生物催化剂将苯乙酮不对称还原为1-苯乙醇的能力。在这些菌株中，季也蒙毕赤酵母P1表现出有效的不对称还原能力。在优化条件下，取代苯乙酮可转化为相应的光学活性仲醇，对映体过量高达99%，且产率高。季也蒙毕赤酵母P1对4-硝基苯乙酮（1m）进行制备规模的不对称生物还原，得到（S）-1-（4-硝基苯基）乙醇（2m），产率为89%，对映体过量>99%。化合物2m已以对映体纯且廉价的形式获得。此外，这些结果表明季也蒙毕赤酵母P1是工业上合成手性醇的一种有前景的生物催化剂。
