Green synthesis of (S)‐1‐(furan‐2‐yl)propan‐1‐ol from asymmetric bioreduction of 1‐(furan‐2‐yl)propan‐1‐one using whole‐cell of Lactobacillus paracasei BD101

• Published in: Chirality (New York, N.Y.) Vol. 36; no. 1; pp. e23620 - n/a
• Main Authors: Bulbul, Ali Savas, Sahin, Engin
• Format: Journal Article
• Language: English
• Published: HOBOKEN Wiley 01.01.2024
• Subjects: (S)‐1‐(furan‐2‐yl)propan‐1‐ol; 1-Propanol; Alcohols; asymmetric bioreduction; Biocatalysis; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Chemistry, Organic; drug precursor; green chemistry; Lacticaseibacillus paracasei; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Phenylpropanolamine; Physical Sciences; Science & Technology; Stereoisomerism; whole‐cell biocatalyst; asymmetric bioreduction; AMINO-ALCOHOLS; FURANS; 2-FURYLMETHANOL; SHARPLESS KINETIC RESOLUTION; green chemistry; BIOCATALYSIS; ENANTIOSELECTIVE BIOREDUCTION; (+)-ASPERLIN; DIETHYLZINC; PRODUCTS; (S)-1-(furan-2-yl)propan-1-ol; whole-cell biocatalyst; drug precursor; DERIVATIVES
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.23620

Chiral heterocyclic alcohols are important precursors for production of pharmaceutical medicines and natural products. (S)‐1‐(furan‐2‐yl)propan‐1‐ol ((S)‐2) can be used production of pyranone, which can be used in the synthesis of sugar analogues, antibiotics, tirantamycines, and anticancer drugs. The synthetic approaches for (S)‐2, however, have substantial difficulties in terms of inadequate enantiomeric excess (ee) and gram scale synthesis. Moreover, the biocatalytic synthesis of (S)‐2 is unknown until now. In this study, the synthesis of (S)‐2 was carried out by performing the asymmetric bioreduction of 1‐(furan‐2‐yl)propan‐1‐one (1) using the Lactobacillus paracasei BD101 biocatalyst obtained from boza, a grain‐based fermented beverage. (S)‐2 was obtained with >99% conversion, >99% ee, and 96% yield under the optimized conditions. Furthermore, in 50 h, 8.37 g of 1 was entirely transformed into (S)‐2 on gram scale (96% isolated yield, 8.11 g). This is the first report on the high‐gram scale biocatalyzed synthesis of enantiopure (S)‐2. These data suggest that L. paracasei BD101 can be used to bioreduction of 1 in gram scale and efficiently produce (S)‐2. Furthermore, these findings laid the base for future study into the biocatalytic production of (S)‐2. It was particularly notable as it was the highest known to date optical purity of (S)‐2 generated by asymmetric reduction using a biocatalyst. This work offers a productive environmentally friendly method for producing (S)‐2 using biocatalysts.