Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 9, Issue 18, Pages 6400-6409Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.1c00993
Keywords
4-hydroxyphenylacetic acid; homovanillic acid; 3,4-dihydroxyphenylacetic acid; lignocellulosic hydrolysate; bioconversion; p-couniaric acid; ferulic acid
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Funding
- Science and Technology Commission of Shanghai Municipality [18JC1413600]
- National Key R&D Program of China [2019YFA0904800]
- National Natural Science Foundation of China [31870071]
- Oceanic Interdisciplinary Program of Shanghai Jiao Tong University [SL2020MS028]
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This study successfully promotes the efficient biosynthesis of hydroxyphenylacetic acids by engineering an E. coli strain and developing a one-pot bioconversion strategy using lignin-related acids as starting materials. The study demonstrates a new strategy for the sustainable synthesis of hydroxyphenylacetic acids and provides insights into the utilization of lignocellulosic biomass in the production of high-value compounds.
4-Hydroxyphenylacetic, homovanillic, and 3,4-dihydroxyphenylacetic acids are phenolic acids with various attractive bioactivities, such as antioxidative, anti-inflammatory, and antiobesity effects. However, powerful strategies for the efficient and sustainable synthesis of hydroxyphenylacetic acids are lacking. In this work, to promote the synthesis of hydroxyphenylacetic acids, we first engineered an Escherichia coli BL21 (DE3)-reduced aromatic aldehyde reduction strain to accumulate their aromatic aldehyde precursors. Then, we developed a one-pot bioconversion strategy using lignin-related p-coumaric and ferulic acids as starting materials for the abovementioned synthesis. The bioconversions comprise two artificial routes: decarboxylation-epoxidationisomerization-oxidation for the synthesis of 4-hydroxyphenylacetic and homovanillic acids and decarboxylation-epoxidationisomerization-oxidation-hydroxylation for the synthesis of 3,4-dihydroxyphenylacetic acid. This enabled efficient biosynthesis of 4-hydroxyphenylacetic acid (13.7 mM, 91.3% yield, 1041 mg/L/h productivity), homovanillic acid (3.8 mM, 76.2% yield, 115.6 mg/L/h productivity), and 3,4-dihydroxyphenylacetic acid (13.5 mM, 90% yield, 907 mg/L/h productivity). Moreover, we made an example to investigate the synthesis of hydroxyphenylacetic acids from the lignocellulosic biomass hydrolysate, in which 5.2 mM 4-hydroxyphenylacetic acid in 57.8% conversion and 2.2 mM 3,4-dihydroxyphenylacetic acid in 55% conversion were produced from 9 and 4 mM p-coumaric acid, respectively. This study provides not only a new strategy to enable the efficient and sustainable synthesis of hydroxyphenylacetic acids but also new insights into the utilization of lignocellulosic biomass in the synthesis of high-value compounds.
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