Highly Efficient Chemoenzymatic Synthesis of l-Phosphinothricin from N-Phenylacetyl-d,l-phosphinothricin by a Robust Immobilized Amidase,Journal of Agricultural and Food Chemistry

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Highly Efficient Chemoenzymatic Synthesis of l-Phosphinothricin from N-Phenylacetyl-d,l-phosphinothricin by a Robust Immobilized Amidase
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-11-24 , DOI: 10.1021/acs.jafc.0c06238
Chao-Ping Lin _{1,

2} , Yue Mao _{1,

2} , Ren-Chao Zheng _{1,

2} , Yu-Guo Zheng _{1,

2}

Affiliation

A chemoenzymatic strategy was developed for the highly efficient synthesis of l-phosphinothricin employing a robust immobilized amidase. An enzymatic hydrolysis of 500 mM N-phenylacetyl-d,l-phosphinothricin resulted in 49.9% conversion and 99.9% ee of l-phosphinothricin within 6 h. To further evaluate the bioprocess for l-phosphinothricin production, the biotransformation was performed for 100 batches under a stirred tank reactor with an average productivity of 8.21 g L^–1 h^–1. Moreover, unreacted N-phenylacetyl-d-phosphinothricin was racemized and subjected to the enzymatic hydrolysis, giving l-phosphinothricin with a 22.3% yield. A total yield of 69.4% was achieved after one recycle of N-phenylacetyl-d-phosphinothricin. Significantly, this chemoenzymatic approach shows great potential in the industrial production of l-phosphinothricin.

中文翻译：

强大的固定化酰胺酶从N-苯基乙酰基-d，l-膦丝菌素高效化学合成l-膦丝菌素

已开发出一种化学酶联策略，以利用稳固的固定化酰胺酶高效合成1-膦丝菌素。500 mM N-苯基乙酰基-d，1-膦丝菌素的酶促水解在6小时内产生了49.9％的转化率和99.9％ee的1-膦丝菌素。为了进一步评估1-膦丝菌素生产的生物过程，在搅拌釜反应器中进行了100批次的生物转化，平均转化率为8.21 g L ^–1 h ^–1。此外，未反应的N-苯基乙酰基-d使-膦丝菌素外消旋并进行酶水解，得到1-膦丝菌素，收率为22.3％。的69.4％的总产率的一个循环后获得Ñ -phenylacetyl- d -phosphinothricin。重要的是，这种化学酶学方法在1-膦丝菌素的工业生产中显示出巨大的潜力。

更新日期：2020-12-09

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