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,Chirality

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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
Chirality ( IF 2.8 ) Pub Date : 2023-09-20 , DOI: 10.1002/chir.23620
Ali Savaş Bülbül ₁ , Engin Şahin ₂

Affiliation

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.

中文翻译：

利用副干酪乳杆菌 BD101 的全细胞，通过 1-(呋喃-2-基)丙-1-酮的不对称生物还原，绿色合成 (S)-1-(呋喃-2-基)丙-1-醇

手性杂环醇是生产药物和天然产物的重要前体。 ( S )-1-(呋喃-2-基)丙-1-醇( ( S )-2 )可用于生产吡喃酮，吡喃酮可用于合成糖类似物、抗生素、替雷霉素、抗癌药物等。然而， ( S )-2的合成方法在对映体过量(ee)和克级合成不足方面存在很大困难。此外， ( S )-2的生物催化合成至今仍未知。在本研究中，使用从谷物 Boza 中获得的副干酪乳杆菌BD101 生物催化剂，通过对 1-(呋喃-2-基)丙-1-酮 ( 1 ) 进行不对称生物还原来合成( S )-2。为基础的发酵饮料。在优化条件下，获得了( S )-2 ，转化率>99%，ee>99%，产率96%。此外，在50小时内，8.37克1完全转化为克级的( S )-2 （分离产率96%，8.11克）。这是第一篇关于高克规模生物催化合成对映体纯( S )-2的报道。这些数据表明副干酪乳杆菌BD101可用于克级生物还原1并有效生产( S )-2 。此外，这些发现为未来研究( S )-2的生物催化生产奠定了基础。它特别值得注意，因为它是迄今为止已知的使用生物催化剂不对称还原产生的( S )-2的最高光学纯度。这项工作提供了一种利用生物催化剂生产( S )-2 的高效环保方法。

更新日期：2023-09-20

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