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不同蓝藻菌株对苯乙酮作为模型底物的还原能力 - 用于手性砌块合成的应用前景。

Reductive capabilities of different cyanobacterial strains towards acetophenone as a model substrate - Prospect of applications for chiral building blocks synthesis.

机构信息

Wroclaw University of Science and Technology, Poland.

Wroclaw University of Science and Technology, Poland.

出版信息

Bioorg Chem. 2019 Dec;93:102810. doi: 10.1016/j.bioorg.2019.02.035. Epub 2019 Feb 26.

DOI:10.1016/j.bioorg.2019.02.035
PMID:30819508
Abstract

Bioreductive capabilities of four morphologically different strains of cyanobacteria have been assessed in this work. Arthrospira maxima, Leptolyngbya foveolarum, Nodularia sphaerocarpa and Synechococcus bigranulatus were applied as catalysts for the reduction of acetophenone to the corresponding chiral phenylethyl alcohol. The process was modified regarding substrate concentration, duration of pre-cultivation period, duration of biotransformation, light regime and glucose addition to the culture media. Obtained results clearly showed that cyanobacteria were active towards acetophenone what resulted in the substrate reduction to (S)-1-phenylethanol with high enantiomeric excess. The reaction efficiency increased with the biotransformation time, but the higher concentration of substrate limited the process yield. Also, all tested strains performed reaction with the highest efficacy under continuous light regime. The most active strains - N. sphaerocarpa and S. bigranulatus carried out the conversion of 1 mM acetophenone with high efficiency of respectively 97.6% and 96.2% after 13 days of biotransformation. A. maxima reached 45.8% of conversion after 13 days of biotransformation whereas L. foveolarum did not exceed 20%. The enantiomeric excesses were respectively 98.8%- A. maxima, 91.7%- L. foveolarum, 72.6%- S. bigranulatus and N. sphaerocarpa 16.2%.

摘要

在这项工作中,评估了四种形态不同的蓝藻菌株的生物还原能力。应用最大螺旋藻、凹脐螺旋藻、鱼腥藻和鱼腥藻作为催化剂,将苯乙酮还原为相应的手性苯乙醇。该过程对底物浓度、预培养期持续时间、生物转化期持续时间、光照制度和葡萄糖添加到培养基进行了修改。得到的结果清楚地表明,蓝藻对苯乙酮具有活性,导致底物还原为(S)-1-苯乙醇,具有高对映体过量。反应效率随生物转化时间的增加而增加,但较高的底物浓度限制了反应收率。此外,所有测试的菌株在连续光照制度下表现出最高的反应效率。最活跃的菌株——鱼腥藻和鱼腥藻在 13 天的生物转化后,以 97.6%和 96.2%的高效分别进行了 1mM 苯乙酮的转化。最大螺旋藻在 13 天的生物转化后达到 45.8%的转化率,而凹脐螺旋藻的转化率不超过 20%。对映体过量分别为 98.8%-最大螺旋藻、91.7%-凹脐螺旋藻、72.6%-鱼腥藻和鱼腥藻 16.2%。

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