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Title: Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals

Abstract

Naturally, many aerobic organisms degrade lignin-derived aromatics through conserved intermediates including protocatechuate and catechol. Employing this microbial approach offers a potential solution for valorizing lignin into valuable chemicals for a potential lignocellulosic biorefinery and enabling bioeconomy. In this study, two hybrid biochemical routes combining lignin chemical depolymerization, plant metabolic engineering, and synthetic pathway reconstruction were demonstrated for valorizing lignin into value-added products. In the biochemical route 1, alkali lignin was chemically depolymerized into vanillin and syringate as major products, which were further bio-converted into cis, cis-muconic acid (ccMA) and pyrogallol, respectively, using engineered Escherichia coli strains. In the second biochemical route, the shikimate pathway of Tobacco plant was engineered to accumulate protocatechuate (PCA) as a soluble intermediate compound. The PCA extracted from the engineered Tobacco was further converted into ccMA using the engineered E. coli strain. This study reports a direct process for converting lignin into ccMA and pyrogallol as value-added chemicals, and more importantly demonstrates benign methods for valorization of polymeric lignin that is inherently heterogeneous and recalcitrant. Our approach also validates the promising combination of plant engineering with microbial chassis development for the production of value added and speciality chemicals.

Authors:
 [1]; ORCiD logo [2];  [2];  [3];  [3];  [3];  [4]
  1. Sandia National Lab. (SNL-CA), Livermore, CA (United States). Dept. of Biomass Science & Conversion Technologies
  2. Sandia National Lab. (SNL-CA), Livermore, CA (United States). Dept. of Biomass Science & Conversion Technologies
  3. Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States)
  4. Sandia National Lab. (SNL-CA), Livermore, CA (United States). Dept. of Biomass Science & Conversion Technologies; Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Univ. of Minnesota, Minneapolis, MN (United States). Dept. of Bioproducts and Biosystems Engineering
Publication Date:
Research Org.:
Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1624321
Grant/Contract Number:  
AC04-94AL85000
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Scientific Reports
Additional Journal Information:
Journal Volume: 7; Journal Issue: 1; Journal ID: ISSN 2045-2322
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
Science & Technology - Other Topics

Citation Formats

Wu, Weihua, Dutta, Tanmoy, Varman, Arul M., Eudes, Aymerick, Manalansan, Bianca, Loqué, Dominique, and Singh, Seema. Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals. United States: N. p., 2017. Web. doi:10.1038/s41598-017-07895-1.
Wu, Weihua, Dutta, Tanmoy, Varman, Arul M., Eudes, Aymerick, Manalansan, Bianca, Loqué, Dominique, & Singh, Seema. Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals. United States. https://doi.org/10.1038/s41598-017-07895-1
Wu, Weihua, Dutta, Tanmoy, Varman, Arul M., Eudes, Aymerick, Manalansan, Bianca, Loqué, Dominique, and Singh, Seema. 2017. "Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals". United States. https://doi.org/10.1038/s41598-017-07895-1. https://www.osti.gov/servlets/purl/1624321.
@article{osti_1624321,
title = {Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals},
author = {Wu, Weihua and Dutta, Tanmoy and Varman, Arul M. and Eudes, Aymerick and Manalansan, Bianca and Loqué, Dominique and Singh, Seema},
abstractNote = {Naturally, many aerobic organisms degrade lignin-derived aromatics through conserved intermediates including protocatechuate and catechol. Employing this microbial approach offers a potential solution for valorizing lignin into valuable chemicals for a potential lignocellulosic biorefinery and enabling bioeconomy. In this study, two hybrid biochemical routes combining lignin chemical depolymerization, plant metabolic engineering, and synthetic pathway reconstruction were demonstrated for valorizing lignin into value-added products. In the biochemical route 1, alkali lignin was chemically depolymerized into vanillin and syringate as major products, which were further bio-converted into cis, cis-muconic acid (ccMA) and pyrogallol, respectively, using engineered Escherichia coli strains. In the second biochemical route, the shikimate pathway of Tobacco plant was engineered to accumulate protocatechuate (PCA) as a soluble intermediate compound. The PCA extracted from the engineered Tobacco was further converted into ccMA using the engineered E. coli strain. This study reports a direct process for converting lignin into ccMA and pyrogallol as value-added chemicals, and more importantly demonstrates benign methods for valorization of polymeric lignin that is inherently heterogeneous and recalcitrant. Our approach also validates the promising combination of plant engineering with microbial chassis development for the production of value added and speciality chemicals.},
doi = {10.1038/s41598-017-07895-1},
url = {https://www.osti.gov/biblio/1624321}, journal = {Scientific Reports},
issn = {2045-2322},
number = 1,
volume = 7,
place = {United States},
year = {Mon Aug 21 00:00:00 EDT 2017},
month = {Mon Aug 21 00:00:00 EDT 2017}
}

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Cited by: 102 works
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Works referenced in this record:

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Lignin depolymerization via an integrated approach of anode oxidation and electro-generated H2O2 oxidation
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The pros and cons of lignin valorisation in an integrated biorefinery
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Heterogeneous Oxidation of Catechol
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Oxidative Cracking of Precipitated Hardwood Lignin by Hydrogen Peroxide
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Decoding how a soil bacterium extracts building blocks and metabolic energy from ligninolysis provides road map for lignin valorization
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The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
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Lignin Depolymerization and Conversion A Review of Thermochemical Methods
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Muconic acid production from glucose using enterobactin precursors in Escherichia coli
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In-frame linker insertion mutagenesis of yeast transposon Ty1: phenotypic analysis
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Efficient valorization of lignin depolymerization products in the present of Ni Mg1−O
journal, November 2015


Biotechnological production of muconic acid: current status and future prospects
journal, May 2014


Exploring bacterial lignin degradation
journal, April 2014


Engineering of plant cell walls for enhanced biofuel production
journal, June 2015


Physicochemical characterisation of sugar cane bagasse lignin oxidized by hydrogen peroxide
journal, April 2010


Metabolic engineering of muconic acid production in Saccharomyces cerevisiae
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Knocking on Wood: Base Metal Complexes as Catalysts for Selective Oxidation of Lignin Models and Extracts
journal, June 2015


Heterogeneous Oxidation of Catechol
journal, October 2015


The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
journal, June 2010


Pyrogallol-Based Molecules as Potent Inhibitors of the Antiapoptotic Bcl-2 Proteins
journal, April 2007


Lignin depolymerization via an integrated approach of anode oxidation and electro-generated H2O2 oxidation
journal, January 2014


Lignin depolymerisation strategies: towards valuable chemicals and fuels
journal, January 2014


Lignin valorization through integrated biological funneling and chemical catalysis
journal, August 2014


Valorization of Biomass: Deriving More Value from Waste
journal, August 2012


Uncovering the Lactobacillus plantarum WCFS1 Gallate Decarboxylase Involved in Tannin Degradation
journal, May 2013


Biosynthesis of cis, cis-Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae
journal, September 2012


Biodegradation of alkaline lignin by Bacillus ligniniphilus L1
journal, February 2017


Genetic and Biochemical Investigations on Bacterial Catabolic Pathways for Lignin-Derived Aromatic Compounds
journal, January 2007


Characterization of ligV Essential for Catabolism of Vanillin by Sphingomonas paucimobilis SYK-6
journal, October 2007


Study on the Selectivity of Bleaching with Oxygen-Containing Species
journal, January 1989


Engineering Plant Biomass Lignin Content and Composition for Biofuels and Bioproducts
journal, July 2015


Works referencing / citing this record:

Bioconversion of lignin and its derivatives into polyhydroxyalkanoates: Challenges and opportunities
journal, December 2018


Biotransformation of lignin: Mechanisms, applications and future work
journal, October 2019


Oxidative Depolymerisation of Lignosulphonate Lignin into Low-Molecular-Weight Products with Cu–Mn/δ-Al2O3
journal, March 2019


Potential of Bacillus subtilis from marine environment to degrade aromatic hydrocarbons
journal, July 2019


Preparation and characterization of thermo-sensitive gel with phenolated alkali lignin
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Bioprocess development for muconic acid production from aromatic compounds and lignin
journal, January 2018


Systematic parameterization of lignin for the CHARMM force field
journal, January 2019


Toward engineering E. coli with an autoregulatory system for lignin valorization
journal, March 2018


Hybrid phenolic-inducible promoters towards construction of self-inducible systems for microbial lignin valorization
journal, June 2018


Recent advances in lignin valorization with bacterial cultures: microorganisms, metabolic pathways, and bio-products
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Internalization and accumulation of model lignin breakdown products in bacteria and fungi
journal, July 2019


Overexpression of the Sorghum bicolor SbCCoAOMT alters cell wall associated hydroxycinnamoyl groups
journal, October 2018


Study on the Effect of 1-Butanol Soluble Lignin on Temperature-Sensitive Gel
journal, October 2018


Methyl ketone production by Pseudomonas putida is enhanced by plant‐derived amino acids
journal, April 2019


Isolation of a novel platform bacterium for lignin valorization and its application in glucose-free cis,cis-muconate production
journal, May 2019


Toward engineering E. coli with an autoregulatory system for lignin valorization
journal, March 2018


Hybrid phenolic-inducible promoters towards construction of self-inducible systems for microbial lignin valorization
journal, June 2018


Internalization and accumulation of model lignin breakdown products in bacteria and fungi
journal, July 2019


Overexpression of the Sorghum bicolor SbCCoAOMT alters cell wall associated hydroxycinnamoyl groups
journal, October 2018