Şahin Engin, Serencam Hüseyin, Dertli Enes
Department of Food Engineering, Faculty of Engineering, Bayburt University, Bayburt, Turkey.
Chirality. 2019 Mar;31(3):211-218. doi: 10.1002/chir.23048. Epub 2019 Jan 11.
In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)-cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)-cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)-cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.
在本研究中,共筛选了10株细菌菌株还原环己基(苯基)甲酮1生成相应醇的能力。在这些菌株中,副干酪乳杆菌BD101被发现是将酮还原为相应醇的最成功的生物催化剂。对还原剂副干酪乳杆菌BD101的反应条件进行了系统优化,该菌株在生物还原反应中表现出高对映选择性和转化率。副干酪乳杆菌BD101对环己基(苯基)甲酮(1)进行制备规模的不对称还原反应,得到(S)-环己基(苯基)甲醇(2),产率为92%,对映体过量>99%。进行了制备规模的研究,共制备了5.602 g高对映体纯形式(对映体过量>99%)的(S)-环己基(苯基)甲醇。副干酪乳杆菌BD101已被证明是不对称还原大体积底物的重要生物催化剂。本研究首次展示了以副干酪乳杆菌BD101作为生物催化剂在制备规模上有效合成(S)-环己基(苯基)甲醇的实例。