Abstract Asymmetric reduction studies of heteroaryl ketones, including phenyl(pyridin-2-yl)methanone in enantioselective form with biocatalysts are very few, and chiral heteroaryl alcohols have been synthesized generally in the small scale. In this study, seven bacterial strains have been used to produce the (S)-phenyl(pyridin-2-yl)methanol in high enantiomeric excess and yield. Among the tested strains, Lactobacillus paracasei BD101, was found to be the best biocatalyst for the reducing phenyl(pyridin-2-yl)methanone to the (S)-phenyl(pyridin-2-yl)methanol at gram scale. The asymmetric bioreduction conditions were systematically optimized using L. paracasei BD101, which demonstrated excellent enantioselectivity and high level of conversion for the bioreduction reaction. (S)-phenyl(pyridin-2-yl)methanol, which is an analgesic, was produced enantiomerically pure form in the first time on gram scale using a biocatalyst. In total, 5.857 g of (S)-phenyl(pyridin-2-yl)methanol in enantiomerically pure form (>99% enantiomeric excess) was obtained in 52 h with 93% yield using whole cells of L. paracasei BD101. Enantiomerically pure (S)-phenyl (pyridin-2-yl)methanol, which is an analgesic, was first produced in the gram scale using a biocatalyst with excellent ee (>99%) and yield (93%). Graphical Abstract

中文翻译：

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用副干酪乳杆菌 BD101 生产对映体纯 (S)-苯基(吡啶-2-基)甲醇

摘要 杂芳基酮（包括对映选择性形式的苯基（吡啶-2-基）甲酮）与生物催化剂的不对称还原研究很少，手性杂芳醇已普遍小规模合成。在这项研究中，已使用七种细菌菌株以高对映体过量和产量生产（S）-苯基（吡啶-2-基）甲醇。在所测试的菌株中，副干酪乳杆菌 BD101 被发现是将苯基（吡啶-2-基）甲酮以克规模还原为（S）-苯基（吡啶-2-基）甲醇的最佳生物催化剂。使用副干酪乳杆菌 BD101 系统地优化了不对称生物还原条件，其表现出出色的对映选择性和生物还原反应的高转化率。(S)-苯基(吡啶-2-基)甲醇，这是一种镇痛剂，使用生物催化剂首次以克规模生产对映体纯形式。使用副干酪乳杆菌 BD101 的全细胞，在 52 小时内总共获得 5.857 克（S）-苯基（吡啶-2-基）甲醇（>99% 对映体过量），产率为 93%。对映异构纯的 (S)-苯基 (吡啶-2-基) 甲醇是一种镇痛剂，首先使用具有优异 ee (>99%) 和产率 (93%) 的生物催化剂以克规模生产。图形概要 首先使用具有优异 ee (>99%) 和产率 (93%) 的生物催化剂以克规模生产。图形概要 首先使用具有优异 ee (>99%) 和产率 (93%) 的生物催化剂以克规模生产。图形概要