Bio-derived production of cinnamyl alcohol via a three step biocatalytic cascade and metabolic engineering,Green Chemistry

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Bio-derived production of cinnamyl alcohol via a three step biocatalytic cascade and metabolic engineering
Green Chemistry ( IF 9.3 ) Pub Date : 2018-01-05 00:00:00 , DOI: 10.1039/c7gc03325g
Evaldas Klumbys ₁ , Ziga Zebec ₁ , Nicholas J Weise ₁ , Nicholas J Turner ₁ , Nigel S Scrutton ₁

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The construction of biocatalytic cascades for the production of chemical precursors is fast becoming one of the most efficient approaches to multi-step synthesis in modern chemistry. However, despite the use of low solvent systems and renewably resourced catalysts in reported examples, many cascades are still dependent on petrochemical starting materials, which as of yet cannot be accessed in a sustainable fashion. Herein, we report the production of the versatile chemical building block cinnamyl alcohol from the primary metabolite and the fermentation product L-phenylalanine. Through the combination of three biocatalyst classes (phenylalanine ammonia lyase, carboxylic acid reductase and alcohol dehydrogenase) the target compound could be obtained in high purity, demonstrable at the 100 mg scale and achieving 53% yield using ambient temperature and pressure in an aqueous solution. This system represents a synthetic strategy in which all components present at time zero are biogenic and thus minimises damage to the environment. Furthermore we extend this biocatalytic cascade by its inclusion in an L-phenylalanine overproducing strain of Escherichia coli. This metabolically engineered strain produces cinnamyl alcohol in mineral media using glycerol and glucose as the carbon sources. This study demonstrates the potential to establish green routes to the synthesis of cinnamyl alcohol from a waste stream such as glycerol derived, for example, from lipase treated biodiesel.

中文翻译：

通过三步生物催化级联和代谢工程生物衍生生产肉桂醇

用于生产化学前体的生物催化级联的构建正迅速成为现代化学中多步合成的最有效方法之一。然而，尽管在报道的例子中使用了低溶剂系统和可再生资源催化剂，但许多级联仍然依赖于石化原材料，而这些原材料迄今为止还无法以可持续的方式获得。在此，我们报道了从初级代谢物和发酵产物L-苯丙氨酸生产多功能化学结构单元肉桂醇。通过组合三种生物催化剂（苯丙氨酸解氨酶、羧酸还原酶和醇脱氢酶），可以获得高纯度的目标化合物，可在 100 毫克规模上进行验证，并在环境温度和压力下在水溶液中实现 53% 的产率。该系统代表了一种合成策略，其中在时间为零时存在的所有成分都是生物源的，从而最大限度地减少对环境的损害。此外，我们通过将其包含在L-苯丙氨酸过量生产的大肠杆菌菌株中来扩展这种生物催化级联。这种代谢工程菌株使用甘油和葡萄糖作为碳源在矿物介质中产生肉桂醇。这项研究证明了建立从废物流（例如源自脂肪酶处理的生物柴油的甘油）合成肉桂醇的绿色路线的潜力。

更新日期：2018-02-06

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