Faculty of Health Sciencies, Department of Nutrition and Dietetics, Bayburt University, Bayburt, Turkey.
Chirality. 2019 Oct;31(10):892-897. doi: 10.1002/chir.23123. Epub 2019 Aug 19.
Optically active aromatic alcohols are valuable chiral building blocks of many natural products and chiral drugs. Lactobacillus paracasei BD87E6, which was isolated from a cereal-based fermented beverage, was shown as a biocatalyst for the bioreduction of 1-(benzofuran-2-yl) ethanone to (S)-1-(benzofuran-2-yl) ethanol with highly stereoselectivity. The bioreduction conditions were optimized using L. paracasei BD87E6 to obtain high enantiomeric excess (ee) and conversion. After optimization of the bioreduction conditions, it was shown that the bioreduction of 1-(benzofuran-2-yl)ethanone was performed in mild reaction conditions. The asymmetric bioreduction of the 1-(benzofuran-2-yl)ethanone had reached 92% yield with ee of higher than 99.9% at 6.73 g of substrate. Our study gave the first example for enantiopure production of (S)-1-(benzofuran-2-yl)ethanol by a biological green method. This process is also scalable and has potential in application. In this study, a basic and novel whole-cell mediated biocatalytic method was performed for the enantiopure production of (S)-1-(benzofuran-2-yl)ethanol in the aqueous medium, which empowered the synthesis of a precious chiral intermediary process to be converted into a sophisticated molecule for drug production.
光学活性芳香醇是许多天然产物和手性药物的有价值的手性构建块。从谷物发酵饮料中分离出的副干酪乳杆菌 BD87E6 被证明是 1-（苯并呋喃-2-基）乙酮生物还原为（S）-1-（苯并呋喃-2-基）乙醇的生物催化剂，具有高度的立体选择性。使用副干酪乳杆菌 BD87E6 优化了生物还原条件，以获得高对映体过量（ee）和转化率。在优化生物还原条件后，表明 1-（苯并呋喃-2-基）乙酮的生物还原在温和的反应条件下进行。在 6.73 g 底物下，不对称生物还原 1-（苯并呋喃-2-基）乙酮的收率达到 92%，ee 值高于 99.9%。我们的研究为通过生物绿色方法生产（S）-1-（苯并呋喃-2-基）乙醇提供了第一个实例。该过程还具有可扩展性，在应用方面具有潜力。在这项研究中，在水相介质中进行了基本的新型全细胞介导的生物催化方法，用于（S）-1-（苯并呋喃-2-基）乙醇的对映体纯生产，这使得合成珍贵的手性中间过程能够转化为用于药物生产的复杂分子。
