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Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst
Biocatalysis and Biotransformation ( IF 1.4 ) Pub Date : 2019-02-10 , DOI: 10.1080/10242422.2019.1568416
Caner Tozlu 1 , Engin Şahin 1 , Hüseyin Serencam 1 , Enes Dertli 1
Affiliation  

Abstract In this study, four bacterial strains were tested for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Weissella paramesenteroides N7 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for W. paramesenteroides N7 that resulted in high enantioselectivity and conversion rates for the bioreduction. The scale-up asymmetric reduction of 1-(4-methoxyphenyl) propan-1-one (1r) by W. paramesenteroides N7 gave (R)-1-(4-methoxyphenyl) propan-1-ol (2r) with 94% yield and >99% enantiomeric excess. This is the first report showing the synthesis of (R)-1-(4-methoxyphenyl) propan-1-ol (2r) in enantiopure form using a biocatalyst on a gram scale. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that W. paramesenteroides N7 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest as a promising and alternative green approach. Graphical Abstract Weissella paramesenteroides as a food originated yeast species is capable of bioreduction of prochiral ketones to secondary chiral alcohols in one enantiomeric form.

中文翻译:

使用Weissellella paramesenteroides作为新型全细胞生物催化剂生产对映体富集的手性甲醇

摘要 在这项研究中,测试了四种细菌菌株将苯乙酮还原为其相应酒精的能力。在这些菌株中,Weissellella paramesenteroides N7 被发现是最成功的将酮还原为相应醇的生物催化剂。系统地优化了 W. paramesenteroides N7 的反应条件,导致生物还原的高对映选择性和转化率。W. paramesenteroides N7 对 1-(4-甲氧基苯基) 丙-1-酮 (1r) 的放大不对称还原得到 (R)-1-(4-甲氧基苯基) 丙-1-醇 (2r),94%产率和 >99% 的对映体过量。这是第一份显示使用生物催化剂以克规模合成对映体纯形式的 (R)-1-(4-甲氧基苯基) 丙-1-醇 (2r) 的报告。整个细胞在制备规模上催化酮底物的还原,证明 W. paramesenteroides N7 将是一种有价值的生物催化剂,用于制备具有药用价值的手性芳香醇,作为一种有前途的替代绿色方法。图形摘要作为一种食物来源的酵母菌种,肠系膜旁白氏菌能够将前手性酮生物还原为一种对映体形式的仲手性醇。
更新日期:2019-02-10
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