There is a considerable interest in the asymmetric production of chiral allylic alcohols, the main building blocks of many functional molecules. The asymmetric reduction of α,β-unsaturated ketones is difficult with traditional chemical protocols in a regioselective and stereoselective manner. In this study, the reductive capacity of whole cell of Leuconostoc mesenteroides N6, Weissella paramesenteroides N7, Weissella cibaria N9, and Leuconostoc pseudomesenteroides N13 was investigated as whole-cell biocatalysts in the enantioselective reduction of (E)-4-phenylbut-3-en-2-one (1). The biocatalytic reduction of 1 to (S,E)-4-phenylbut-3-en-2-ol ((S,E)-2) using the whole cell of W. cibaria N9 isolated from Turkish sourdough was developed in a regioselective fashion, occurring with excellent conversion and recovering the product in good yield. In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. In addition, to our knowledge, this is the first report on production of (S,E)-2 using whole-cell biocatalyst in excellent yield, conversion with enantiopure form and at gram scale. These findings pave the way for the use of whole cell of W. cibaria N9 for challenging higher substrate concentrations of different α,β-unsaturated ketones for regioselective reduction at industrial scale.

中文翻译：

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Weissella cibaria N9生物催化剂全细胞对trans-4-phenylbut-3-en-2-one的区域选择性不对称生物还原

手性烯丙醇的不对称生产引起了人们极大的兴趣，这是许多功能分子的主要组成部分。α,β-不饱和酮的不对称还原很难通过传统的化学方案以区域选择性和立体选择性的方式进行。在这项研究中，将全细胞的还原能力肠膜明串珠N6，魏斯氏paramesenteroides N7，魏斯氏cibaria N9，和明串珠菌属pseudomesenteroides N13在对映选择性还原的（被研究作为全细胞生物催化剂ë）-4-苯基丁-3-烯-2-一 ( 1 )。生物催化还原的1至（小号，ê)-4-phenylbut-3-en-2-ol ( ( S , E )-2 ) 使用W的整个细胞。 从土耳其酸面团中分离出的cibaria N9 是以区域选择性方式开发的，具有出色的转化率并以良好的收率回收产品。在生物催化还原反应中，底物的转化和产物的对映体过量 (ee) 受到温度、搅拌速率、pH 和孵育时间等优化参数的显着影响。综合研究了这些参数对ee和转化率的影响。此外，据我们所知，这是关于( S , E )-2产生的第一份报告以优异的产率使用全细胞生物催化剂，以对映体纯形式和克级规模进行转化。这些发现为使用W的全细胞铺平了道路。 cibaria N9 用于挑战更高底物浓度的不同 α,β-不饱和酮，用于工业规模的区域选择性还原。