Green synthesis of enantiopure (S)‐1‐(benzofuran‐2‐yl)ethanol by whole‐cell biocatalyst

• Published in: Chirality (New York, N.Y.) N.Y.), 2019-10, Vol.31 (10), p.892-897
• Main Author: Şahin, Engin
• Format: Article
• Language: English
• Subjects: (S)‐1‐(benzofuran‐2‐yl)ethanol; Alcohols; Aqueous solutions; asymmetric bioreduction; Benzofuran; Benzofurans - chemical synthesis; Biocatalysis; Biocatalysts; Biological activity; chirality; Ethanol; Ethanol - analogs & derivatives; Ethanol - chemical synthesis; Fermented food; Green Chemistry Technology - methods; Hydrogen-Ion Concentration; Lactobacillus paracasei; Lactobacillus paracasei - isolation & purification; Lactobacillus paracasei - metabolism; Lactobacillus paracasei BD87E6; Natural products; Optical activity; Optimization; Stereoisomerism; Stereoselectivity; Substrates; Synthesis; Temperature; whole‐cell biocatalysts
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.23123

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.