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Title: Promoting microbial utilization of phenolic substrates from bio-oil

Abstract

The economic viability of the biorefinery concept is limited by the valorization of lignin. One possible method of lignin valorization is biological upgrading with aromatic-catabolic microbes. In conjunction, lignin monomers can be produced by fast pyrolysis and fractionation. However, biological upgrading of these lignin monomers is limited by low water solubility. Here, we address the problem of low water solubility with an emulsifier blend containing approximately 70 wt% Tween® 20 and 30 wt% Span® 80. Pseudomonas putida KT2440 grew to an optical density (OD600) of 1.0 ± 0.2 when supplied with 1.6 wt% emulsified phenolic monomer-rich product produced by fast pyrolysis of red oak using an emulsifier dose of 0.076 ± 0.002g emulsifier blend per g of phenolic monomer-rich product. This approach partially mitigated the toxicity of the model phenolic monomer p-coumarate to the microbe, but not benzoate or vanillin. This study provides a proof of concept that processing of biomass-derived phenolics to increase aqueous availability can enhance microbial utilization.

Authors:
 [1];  [2]; ORCiD logo [3];  [2]; ORCiD logo [3];  [4];  [2];  [1]
  1. Iowa State Univ., Ames, IA (United States). Chemical and Biological Engineering
  2. Iowa State Univ., Ames, IA (United States). Bioeconomy Inst.
  3. National Renewable Energy Laboratory (NREL), Golden, CO (United States)
  4. Iowa State Univ., Ames, IA (United States). Dept. of Food Science and Human Nutrition
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1543118
Report Number(s):
NREL/JA-5100-74319
Journal ID: ISSN 1367-5435
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Industrial Microbiology and Biotechnology
Additional Journal Information:
Journal Volume: none; Journal Issue: none; Journal ID: ISSN 1367-5435
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; Pseudomonas putida KT2440; lignin; bio-oil; emulsion; phenols

Citation Formats

Davis, Kirsten, Rover, Marjorie R., Salvachua Rodriguez, Davinia, Smith, Ryan G., Beckham, Gregg T, Wen, Zhiyou, Brown, Robert C., and Jarboe, Laura R. Promoting microbial utilization of phenolic substrates from bio-oil. United States: N. p., 2019. Web. doi:10.1007/s10295-019-02208-z.
Davis, Kirsten, Rover, Marjorie R., Salvachua Rodriguez, Davinia, Smith, Ryan G., Beckham, Gregg T, Wen, Zhiyou, Brown, Robert C., & Jarboe, Laura R. Promoting microbial utilization of phenolic substrates from bio-oil. United States. doi:10.1007/s10295-019-02208-z.
Davis, Kirsten, Rover, Marjorie R., Salvachua Rodriguez, Davinia, Smith, Ryan G., Beckham, Gregg T, Wen, Zhiyou, Brown, Robert C., and Jarboe, Laura R. Thu . "Promoting microbial utilization of phenolic substrates from bio-oil". United States. doi:10.1007/s10295-019-02208-z. https://www.osti.gov/servlets/purl/1543118.
@article{osti_1543118,
title = {Promoting microbial utilization of phenolic substrates from bio-oil},
author = {Davis, Kirsten and Rover, Marjorie R. and Salvachua Rodriguez, Davinia and Smith, Ryan G. and Beckham, Gregg T and Wen, Zhiyou and Brown, Robert C. and Jarboe, Laura R.},
abstractNote = {The economic viability of the biorefinery concept is limited by the valorization of lignin. One possible method of lignin valorization is biological upgrading with aromatic-catabolic microbes. In conjunction, lignin monomers can be produced by fast pyrolysis and fractionation. However, biological upgrading of these lignin monomers is limited by low water solubility. Here, we address the problem of low water solubility with an emulsifier blend containing approximately 70 wt% Tween® 20 and 30 wt% Span® 80. Pseudomonas putida KT2440 grew to an optical density (OD600) of 1.0 ± 0.2 when supplied with 1.6 wt% emulsified phenolic monomer-rich product produced by fast pyrolysis of red oak using an emulsifier dose of 0.076 ± 0.002g emulsifier blend per g of phenolic monomer-rich product. This approach partially mitigated the toxicity of the model phenolic monomer p-coumarate to the microbe, but not benzoate or vanillin. This study provides a proof of concept that processing of biomass-derived phenolics to increase aqueous availability can enhance microbial utilization.},
doi = {10.1007/s10295-019-02208-z},
journal = {Journal of Industrial Microbiology and Biotechnology},
number = none,
volume = none,
place = {United States},
year = {2019},
month = {7}
}

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Multi-step separation of monophenols and pyrolytic lignins from the water-insoluble phase of bio-oil
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Bioprocess development for muconic acid production from aromatic compounds and lignin
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Effect of selected aldehydes on the growth and fermentation of ethanologenic Escherichia coli
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Thermochemical wastewater valorization via enhanced microbial toxicity tolerance
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    Works referencing / citing this record:

    Production, separation and applications of phenolic-rich bio-oil – A review
    journal, February 2015


    Gene cloning, identification, and characterization of the multicopper oxidase CumA from Pseudomonas sp. 593 : Caracterization of CumA from
    journal, December 2016

    • Yang, Sheng; Long, Yan; Yan, Hong
    • Biotechnology and Applied Biochemistry, Vol. 64, Issue 3
    • DOI: 10.1002/bab.1501

    Techno-economic analysis of biomass fast pyrolysis to transportation fuels
    journal, November 2010


    Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production ofSaccharomyces cerevisiae: Wet oxidation and fermentation by yeast
    journal, January 2003

    • Klinke, H. B.; Olsson, L.; Thomsen, A. B.
    • Biotechnology and Bioengineering, Vol. 81, Issue 6
    • DOI: 10.1002/bit.10523

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

    • Linger, J. G.; Vardon, D. R.; Guarnieri, M. T.
    • Proceedings of the National Academy of Sciences, Vol. 111, Issue 33, p. 12013-12018
    • DOI: 10.1073/pnas.1410657111

    Adipic acid production from lignin
    journal, January 2015

    • Vardon, Derek R.; Franden, Mary Ann; Johnson, Christopher W.
    • Energy & Environmental Science, Vol. 8, Issue 2
    • DOI: 10.1039/c4ee03230f

    Synergistic enzymatic and microbial lignin conversion
    journal, January 2016

    • Zhao, Cheng; Xie, Shangxian; Pu, Yunqiao
    • Green Chemistry, Vol. 18, Issue 5
    • DOI: 10.1039/c5gc01955a

    Engineering inhibitor tolerance for the production of biorenewable fuels and chemicals
    journal, October 2011

    • Jarboe, Laura R.; Liu, Ping; Royce, Liam A.
    • Current Opinion in Chemical Engineering, Vol. 1, Issue 1
    • DOI: 10.1016/j.coche.2011.08.003

    Multi-step separation of monophenols and pyrolytic lignins from the water-insoluble phase of bio-oil
    journal, February 2014


    Stabilization of bio-oils using low temperature, low pressure hydrogenation
    journal, August 2015


    Nucleotide sequence and functional analysis of the complete phenol/3,4-dimethylphenol catabolic pathway of Pseudomonas sp. strain CF600.
    journal, February 1992


    Aromatic catabolic pathway selection for optimal production of pyruvate and lactate from lignin
    journal, March 2015


    Solubilization and mineralization of polycyclic aromatic hydrocarbons by Pseudomonas putida in the presence of surfactant
    journal, January 2003


    A thermochemical–biochemical hybrid processing of lignocellulosic biomass for producing fuels and chemicals
    journal, December 2015


    Characterization of the emulsions formed by catastrophic phase inversion
    journal, May 2014

    • Lv, Guojun; Wang, Fumin; Cai, Wangfeng
    • Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 450
    • DOI: 10.1016/j.colsurfa.2014.03.023

    Combinatorial pretreatment and fermentation optimization enabled a record yield on lignin bioconversion
    journal, January 2018


    Production of methoxyphenol-type natural aroma chemicals by biotransformation of eugenol with a new Pseudomonas sp.
    journal, December 1996


    Effect of surfactants on the interaction of phenol with laccase: Molecular docking and molecular dynamics simulation studies
    journal, September 2018


    Genome-wide identification of tolerance mechanisms toward p -coumaric acid in Pseudomonas putida
    journal, November 2017

    • Calero, Patricia; Jensen, Sheila I.; Bojanovič, Klara
    • Biotechnology and Bioengineering, Vol. 115, Issue 3
    • DOI: 10.1002/bit.26495

    Metabolic engineering of Corynebacterium glutamicum for the production of cis, cis-muconic acid from lignin
    journal, July 2018


    Estimation of the production cost of fast pyrolysis bio-oil
    journal, January 2012


    Quantification of total phenols in bio-oil using the Folin–Ciocalteu method
    journal, November 2013


    Hydrophobicity and Charge Shape Cellular Metabolite Concentrations
    journal, October 2011


    Properties of water-in-oil (W/O) nano-emulsions prepared by a low-energy emulsification method
    journal, July 2008

    • Porras, M.; Solans, C.; González, C.
    • Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 324, Issue 1-3
    • DOI: 10.1016/j.colsurfa.2008.04.012

    Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin
    journal, November 2007


    Towards lignin consolidated bioprocessing: simultaneous lignin depolymerization and product generation by bacteria
    journal, January 2015

    • Salvachúa, Davinia; Karp, Eric M.; Nimlos, Claire T.
    • Green Chemistry, Vol. 17, Issue 11
    • DOI: 10.1039/c5gc01165e

    Conversion of lignin model compounds by Pseudomonas putida KT2440 and isolates from compost
    journal, March 2017

    • Ravi, Krithika; García-Hidalgo, Javier; Gorwa-Grauslund, Marie F.
    • Applied Microbiology and Biotechnology, Vol. 101, Issue 12
    • DOI: 10.1007/s00253-017-8211-y

    Evaluation of different chemical preservatives to control Zygosaccharomyces rouxii growth in high sugar culture media
    journal, April 2015


    Development of emulsions from biomass pyrolysis liquid and diesel and their use in engines—Part 1 : emulsion production
    journal, July 2003


    Fast pyrolysis of sesame stalk: yields and structural analysis of bio-oil
    journal, June 2004

    • Ateş, F.; Pütün, E.; Pütün, A. E.
    • Journal of Analytical and Applied Pyrolysis, Vol. 71, Issue 2
    • DOI: 10.1016/j.jaap.2003.11.001

    Comparative study of the fast pyrolysis behavior of ginkgo, poplar, and wheat straw lignin at different temperatures
    journal, October 2018


    Synthetic and lignin-based surfactants: Challenges and opportunities
    journal, August 2018


    Bioprocess development for muconic acid production from aromatic compounds and lignin
    journal, January 2018

    • Salvachúa, Davinia; Johnson, Christopher W.; Singer, Christine A.
    • Green Chemistry, Vol. 20, Issue 21
    • DOI: 10.1039/c8gc02519c

    The application of a multi-scale approach to the manufacture of concentrated and highly concentrated emulsions
    journal, March 2015


    Functional Genomics of Stress Response in Pseudomonas putida KT2440
    journal, May 2006

    • Reva, O. N.; Weinel, C.; Weinel, M.
    • Journal of Bacteriology, Vol. 188, Issue 11
    • DOI: 10.1128/jb.00101-06

    Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440
    journal, December 2002


    Enabling biomass combustion and co-firing through the use of Lignocol
    journal, January 2018


    Recovery and Utilization of Lignin Monomers as Part of the Biorefinery Approach
    journal, October 2016

    • Davis, Kirsten; Rover, Marjorie; Brown, Robert
    • Energies, Vol. 9, Issue 10
    • DOI: 10.3390/en9100808

    Rapid degradation of ferulic acid via 4-vinylguaiacol and vanillin by a newly isolated strain of Bacillus coagulans
    journal, July 2000


    Effect of selected aldehydes on the growth and fermentation of ethanologenic Escherichia coli
    journal, October 1999


    Pseudomonas putida as a functional chassis for industrial biocatalysis: From native biochemistry to trans-metabolism
    journal, November 2018


    Breaking Down Lignin to High-Value Chemicals: The Conversion of Lignocellulose to Vanillin in a Gene Deletion Mutant of Rhodococcus jostii RHA1
    journal, August 2013

    • Sainsbury, Paul D.; Hardiman, Elizabeth M.; Ahmad, Mark
    • ACS Chemical Biology, Vol. 8, Issue 10
    • DOI: 10.1021/cb400505a

    A simple and rapid vortex method for preparing antigen/adjuvant emulsions for immunization
    journal, May 2003


    Lignocellulosic ethanol production without enzymes – Technoeconomic analysis of ionic liquid pretreatment followed by acidolysis
    journal, April 2014


    Effect of organic acids on the growth and fermentation of ethanologenicEscherichia coli LY01
    journal, January 1999


    Design of nanoemulsion-based delivery systems of natural antimicrobials: Effect of the emulsifier
    journal, June 2012


    Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis
    journal, June 2016

    • Rinaldi, Roberto; Jastrzebski, Robin; Clough, Matthew T.
    • Angewandte Chemie International Edition, Vol. 55, Issue 29
    • DOI: 10.1002/anie.201510351

    Emulsification of Vegetable Oils using a Blend of Nonionic Surfactants for Cosmetic Applications
    journal, August 2007

    • Rahate, Amar Ramesh; Nagarkar, Jayashree M.
    • Journal of Dispersion Science and Technology, Vol. 28, Issue 7
    • DOI: 10.1080/01932690701524802

    Involvement of acetosyringone in plant–pathogen recognition
    journal, March 2005

    • Baker, C. Jacyn; Mock, Norton M.; Whitaker, Bruce D.
    • Biochemical and Biophysical Research Communications, Vol. 328, Issue 1
    • DOI: 10.1016/j.bbrc.2004.12.153

    Hydrocarbon Liquid Production via Catalytic Hydroprocessing of Phenolic Oils Fractionated from Fast Pyrolysis of Red Oak and Corn Stover
    journal, April 2015


    Bacterial catabolism of lignin-derived aromatics: New findings in a recent decade: Update on bacterial lignin catabolism: Bacterial catabolism of lignin-derived aromatics
    journal, November 2017

    • Kamimura, Naofumi; Takahashi, Kenji; Mori, Kosuke
    • Environmental Microbiology Reports, Vol. 9, Issue 6
    • DOI: 10.1111/1758-2229.12597

    From lignin to nylon: Cascaded chemical and biochemical conversion using metabolically engineered Pseudomonas putida
    journal, May 2018


    Effect of phenolic compounds on bioconversion of glucose to ethanol by yeast Saccharomyces cerevisiae PE-2
    journal, January 2018

    • Lyra Colombi, Bruna; Silva Zanoni, Patrícia Raquel; Benathar Ballod Tavares, Lorena
    • The Canadian Journal of Chemical Engineering, Vol. 96, Issue 7
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    Comparison of product distribution, content and fermentability of biomass in a hybrid thermochemical/biological processing platform
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    The effect of pyrolysis temperature on recovery of bio-oil as distinctive stage fractions
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    • Rover, Marjorie R.; Johnston, Patrick A.; Whitmer, Lysle E.
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    Glucose-Free cis , cis -Muconic Acid Production via New Metabolic Designs Corresponding to the Heterogeneity of Lignin
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    Formation of phenolic oligomers during fast pyrolysis of lignin
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    Mechanisms of Solvent Tolerance in Gram-Negative Bacteria
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    Production of Clean Pyrolytic Sugars for Fermentation
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    Opportunities and challenges in biological lignin valorization
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    Biological valorization of low molecular weight lignin
    journal, December 2016


    Thermochemical wastewater valorization via enhanced microbial toxicity tolerance
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    Characterization of bio-oil recovered as stage fractions with unique chemical and physical properties
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    Biocatalytic conversion of lignin to aromatic dicarboxylic acids in Rhodococcus jostii RHA1 by re-routing aromatic degradation pathways
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