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Title: Scaled-up production of poacic acid, a plant-derived antifungal agent

Poacic acid, a decarboxylated product from 8–5-diferulic acid that is commonly found in monocot lignocellulosic hydrolysates, has been identified as a natural antifungal agent against economically significant fungi and oomycete plant pathogens. Starting from commercially available or monocot-derivable ferulic acid, a three-step synthetic procedure has been developed for the production of poacic acid needed for field testing in a controlled agricultural setting. First, ferulic acid was esterified to produce ethyl ferulate in 92% yield. Second, peroxidase-catalyzed free radical dehydrodimerization of ethyl ferulate produced crude diferulates, mainly 8–5-diferulate, in 91% yield. Finally, crystalline poacic acid was obtained in 25% yield via alkaline hydrolysis of the crude diferulates after purification by flash-column chromatography. Thus, this new procedure offers two key improvements relevant to large-scale production: 1) bubbling air through the reaction mixture in the second step to remove acetone greatly improves the recovery efficiency of the crude diferulates; and 2) telescoping minor impurities directly into the alkaline hydrolysis step eliminates the need for additional column purifications, thus reducing the overall cost of production and removing a major impediment to process scale-up.
Authors:
 [1] ;  [2] ;  [3] ;  [2] ;  [1] ;  [2]
  1. South China Univ. of Technology (SCUT), Guangzhou (China). State Key Lab. of Pulp and Paper Engineering; Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry, Dept. of Plant Pathology, Great Lakes Bioenergy Research Center and Wisconsin Energy Inst.
  2. Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry, Dept. of Plant Pathology, Great Lakes Bioenergy Research Center and Wisconsin Energy Inst.
  3. Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry, Dept. of Plant Pathology, Great Lakes Bioenergy Research Center and Wisconsin Energy Inst.; Yumanity Therapeutics, Cambridge, MA (United States)
Publication Date:
Grant/Contract Number:
FC02-07ER64494; 178899
Type:
Published Article
Journal Name:
Industrial Crops and Products
Additional Journal Information:
Journal Volume: 103; Journal Issue: C; Journal ID: ISSN 0926-6690
Research Org:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES; 59 BASIC BIOLOGICAL SCIENCES; Lignocellulosic hydrolysates; Diferulates; Fungicide; Hydrolysis; Radical coupling
OSTI Identifier:
1393264
Alternate Identifier(s):
OSTI ID: 1427248

Yue, Fengxia, Gao, Ruili, Piotrowski, Jeff S., Kabbage, Mehdi, Lu, Fachuang, and Ralph, John. Scaled-up production of poacic acid, a plant-derived antifungal agent. United States: N. p., Web. doi:10.1016/j.indcrop.2017.03.045.
Yue, Fengxia, Gao, Ruili, Piotrowski, Jeff S., Kabbage, Mehdi, Lu, Fachuang, & Ralph, John. Scaled-up production of poacic acid, a plant-derived antifungal agent. United States. doi:10.1016/j.indcrop.2017.03.045.
Yue, Fengxia, Gao, Ruili, Piotrowski, Jeff S., Kabbage, Mehdi, Lu, Fachuang, and Ralph, John. 2017. "Scaled-up production of poacic acid, a plant-derived antifungal agent". United States. doi:10.1016/j.indcrop.2017.03.045.
@article{osti_1393264,
title = {Scaled-up production of poacic acid, a plant-derived antifungal agent},
author = {Yue, Fengxia and Gao, Ruili and Piotrowski, Jeff S. and Kabbage, Mehdi and Lu, Fachuang and Ralph, John},
abstractNote = {Poacic acid, a decarboxylated product from 8–5-diferulic acid that is commonly found in monocot lignocellulosic hydrolysates, has been identified as a natural antifungal agent against economically significant fungi and oomycete plant pathogens. Starting from commercially available or monocot-derivable ferulic acid, a three-step synthetic procedure has been developed for the production of poacic acid needed for field testing in a controlled agricultural setting. First, ferulic acid was esterified to produce ethyl ferulate in 92% yield. Second, peroxidase-catalyzed free radical dehydrodimerization of ethyl ferulate produced crude diferulates, mainly 8–5-diferulate, in 91% yield. Finally, crystalline poacic acid was obtained in 25% yield via alkaline hydrolysis of the crude diferulates after purification by flash-column chromatography. Thus, this new procedure offers two key improvements relevant to large-scale production: 1) bubbling air through the reaction mixture in the second step to remove acetone greatly improves the recovery efficiency of the crude diferulates; and 2) telescoping minor impurities directly into the alkaline hydrolysis step eliminates the need for additional column purifications, thus reducing the overall cost of production and removing a major impediment to process scale-up.},
doi = {10.1016/j.indcrop.2017.03.045},
journal = {Industrial Crops and Products},
number = C,
volume = 103,
place = {United States},
year = {2017},
month = {9}
}