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Title: Combining metabolic engineering and electrocatalysis: Application to the production of polyamides from sugar

Abstract

Here, biorefineries aim to convert biomass into a spectrum of products ranging from biofuels to specialty chemicals. To achieve economically sustainable conversion, it is crucial to streamline the catalytic and downstream processing steps. In this work, a route that combines bio- and electrocatalysis to convert glucose into bio-based unsaturated nylon-6,6 is reported. An engineered strain of Saccharomyces cerevisiae was used as the initial biocatalyst for the conversion of glucose into muconic acid, with the highest reported muconic acid titer of 559.5 mg L–1 in yeast. Without any separation, muconic acid was further electrocatalytically hydrogenated to 3-hexenedioic acid in 94 % yield despite the presence of biogenic impurities. Bio-based unsaturated nylon-6,6 (unsaturated polyamide-6,6) was finally obtained by polymerization of 3-hexenedioic acid with hexamethylenediamine.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [4]; ORCiD logo [4]; ORCiD logo [3]; ORCiD logo [1]; ORCiD logo [2]
  1. Iowa State Univ., Ames, IA (United States); NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)
  2. Iowa State Univ., Ames, IA (United States); NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States); Ames Lab., Ames, IA (United States)
  3. Iowa State Univ., Ames, IA (United States)
  4. NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1239152
Report Number(s):
IS-J-8730
Journal ID: ISSN 1433-7851
Grant/Contract Number:  
EEC0813570; EPSC1101284; AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 55; Journal Issue: 7; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Suastegui, Miguel, Matthiesen, John E., Carraher, Jack M., Hernandez, Nacu, Rodriguez Quiroz, Natalia, Okerlund, Adam, Cochran, Eric W., Shao, Zengyi, and Tessonnier, Jean -Philippe. Combining metabolic engineering and electrocatalysis: Application to the production of polyamides from sugar. United States: N. p., 2016. Web. doi:10.1002/anie.201509653.
Suastegui, Miguel, Matthiesen, John E., Carraher, Jack M., Hernandez, Nacu, Rodriguez Quiroz, Natalia, Okerlund, Adam, Cochran, Eric W., Shao, Zengyi, & Tessonnier, Jean -Philippe. Combining metabolic engineering and electrocatalysis: Application to the production of polyamides from sugar. United States. https://doi.org/10.1002/anie.201509653
Suastegui, Miguel, Matthiesen, John E., Carraher, Jack M., Hernandez, Nacu, Rodriguez Quiroz, Natalia, Okerlund, Adam, Cochran, Eric W., Shao, Zengyi, and Tessonnier, Jean -Philippe. Thu . "Combining metabolic engineering and electrocatalysis: Application to the production of polyamides from sugar". United States. https://doi.org/10.1002/anie.201509653. https://www.osti.gov/servlets/purl/1239152.
@article{osti_1239152,
title = {Combining metabolic engineering and electrocatalysis: Application to the production of polyamides from sugar},
author = {Suastegui, Miguel and Matthiesen, John E. and Carraher, Jack M. and Hernandez, Nacu and Rodriguez Quiroz, Natalia and Okerlund, Adam and Cochran, Eric W. and Shao, Zengyi and Tessonnier, Jean -Philippe},
abstractNote = {Here, biorefineries aim to convert biomass into a spectrum of products ranging from biofuels to specialty chemicals. To achieve economically sustainable conversion, it is crucial to streamline the catalytic and downstream processing steps. In this work, a route that combines bio- and electrocatalysis to convert glucose into bio-based unsaturated nylon-6,6 is reported. An engineered strain of Saccharomyces cerevisiae was used as the initial biocatalyst for the conversion of glucose into muconic acid, with the highest reported muconic acid titer of 559.5 mg L–1 in yeast. Without any separation, muconic acid was further electrocatalytically hydrogenated to 3-hexenedioic acid in 94 % yield despite the presence of biogenic impurities. Bio-based unsaturated nylon-6,6 (unsaturated polyamide-6,6) was finally obtained by polymerization of 3-hexenedioic acid with hexamethylenediamine.},
doi = {10.1002/anie.201509653},
journal = {Angewandte Chemie (International Edition)},
number = 7,
volume = 55,
place = {United States},
year = {Thu Jan 14 00:00:00 EST 2016},
month = {Thu Jan 14 00:00:00 EST 2016}
}

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Works referenced in this record:

143. Polyene acids. Part V. Catalytic semi-hydrogenation of the three isomeric muconic acids and comfirmation of their configurations
journal, January 1953

  • Elvidge, J. A.; Linstead, R. P.; Smith, John F.
  • Journal of the Chemical Society (Resumed)
  • DOI: 10.1039/jr9530000708

Platform biochemicals for a biorenewable chemical industry
journal, May 2008


Customized optimization of metabolic pathways by combinatorial transcriptional engineering
journal, June 2012

  • Du, Jing; Yuan, Yongbo; Si, Tong
  • Nucleic Acids Research, Vol. 40, Issue 18
  • DOI: 10.1093/nar/gks549

Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited
journal, January 2010

  • Bozell, Joseph J.; Petersen, Gene R.
  • Green Chemistry, Vol. 12, Issue 4, p. 539-554
  • DOI: 10.1039/b922014c

Engineering Escherichia coli coculture systems for the production of biochemical products
journal, June 2015

  • Zhang, Haoran; Pereira, Brian; Li, Zhengjun
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 27
  • DOI: 10.1073/pnas.1506781112

Metabolic engineering of muconic acid production in Saccharomyces cerevisiae
journal, January 2013


The battle for the “green” polymer. Different approaches for biopolymer synthesis: bioadvantaged vs. bioreplacement
journal, January 2014

  • Hernández, Nacú; Williams, R. Christopher; Cochran, Eric W.
  • Org. Biomol. Chem., Vol. 12, Issue 18
  • DOI: 10.1039/C3OB42339E

Biorefineries for the production of top building block chemicals and their derivatives
journal, March 2015


Development of an In Vitro Compartmentalization Screen for High-Throughput Directed Evolution of [FeFe] Hydrogenases
journal, December 2010


Efficient Multiplexed Integration of Synergistic Alleles and Metabolic Pathways in Yeasts via CRISPR-Cas
journal, July 2015


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

Bridging the Chemical and Biological Catalysis Gap: Challenges and Outlooks for Producing Sustainable Chemicals
journal, April 2014

  • Schwartz, Thomas J.; O’Neill, Brandon J.; Shanks, Brent H.
  • ACS Catalysis, Vol. 4, Issue 6
  • DOI: 10.1021/cs500364y

Development of new catalysts for N2O-decomposition from adipic acid plant
journal, January 2007

  • Alini, Stefano; Basile, Francesco; Blasioli, Sonia
  • Applied Catalysis B: Environmental, Vol. 70, Issue 1-4
  • DOI: 10.1016/j.apcatb.2005.12.031

Low Energy Electron Diffraction and Electron Spectroscopic Studies of the Oxidation and Sulphidation of Pb(100) and Pb(110) Surfaces
journal, January 1978

  • Joyner, R. W.; Kishi, K.; Roberts, M. W.
  • Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 358, Issue 1693
  • DOI: 10.1098/rspa.1978.0006

Corrosion and its control
book, January 1993


Transcriptional Repression Mediated by LysR-Type Regulator CatR Bound at Multiple Binding Sites
journal, May 1998


Yeast cell factories on the horizon
journal, September 2015


Benzene-Free Synthesis of Adipic Acid
journal, April 2002

  • Niu, W.; Draths, K. M.; Frost, J. W.
  • Biotechnology Progress, Vol. 18, Issue 2, p. 201-211
  • DOI: 10.1021/bp010179x

Chemical Routes for the Transformation of Biomass into Chemicals
journal, June 2007

  • Corma, Avelino; Iborra, Sara; Velty, Alexandra
  • Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502
  • DOI: 10.1021/cr050989d

Differential glucose repression in common yeast strains in response to HXK2 deletion: Differential glucose repression in common yeast strains
journal, April 2010


RNAi-Assisted Genome Evolution in Saccharomyces cerevisiae for Complex Phenotype Engineering
journal, May 2014

  • Si, Tong; Luo, Yunzi; Bao, Zehua
  • ACS Synthetic Biology, Vol. 4, Issue 3
  • DOI: 10.1021/sb500074a

Alleviation of feedback inhibition in Saccharomyces cerevisiae aromatic amino acid biosynthesis: Quantification of metabolic impact
journal, May 2008


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

Fed-batch fermentor synthesis of 3-dehydroshikimic acid using recombinant Escherichia coli
journal, July 1999


Advanced Biotechnology: Metabolically Engineered Cells for the Bio-Based Production of Chemicals and Fuels, Materials, and Health-Care Products
journal, February 2015

  • Becker, Judith; Wittmann, Christoph
  • Angewandte Chemie International Edition, Vol. 54, Issue 11
  • DOI: 10.1002/anie.201409033

Metabolic engineering of yeast for production of fuels and chemicals
journal, June 2013

  • Nielsen, Jens; Larsson, Christer; van Maris, Antonius
  • Current Opinion in Biotechnology, Vol. 24, Issue 3
  • DOI: 10.1016/j.copbio.2013.03.023

Downstream process for the production of yeast extract using brewer's yeast cells
journal, February 2005

  • In, Man-Jin; Kim, Dong Chung; Chae, Hee Jeong
  • Biotechnology and Bioprocess Engineering, Vol. 10, Issue 1
  • DOI: 10.1007/BF02931188

Engineering Catalyst Microenvironments for Metal-Catalyzed Hydrogenation of Biologically Derived Platform Chemicals
journal, September 2014

  • Schwartz, Thomas J.; Johnson, Robert L.; Cardenas, Javier
  • Angewandte Chemie, Vol. 126, Issue 47
  • DOI: 10.1002/ange.201407615

Engineering Catalyst Microenvironments for Metal-Catalyzed Hydrogenation of Biologically Derived Platform Chemicals
journal, September 2014

  • Schwartz, Thomas J.; Johnson, Robert L.; Cardenas, Javier
  • Angewandte Chemie International Edition, Vol. 53, Issue 47
  • DOI: 10.1002/anie.201407615

CatM Regulation of the benABCDE Operon: Functional Divergence of Two LysR-Type Paralogs in Acinetobacter baylyi ADP1
journal, March 2006


Engineering yeasts for xylose metabolism
journal, June 2006


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

  • Weber, Christian; Brückner, Christine; Weinreb, Sheila
  • Applied and Environmental Microbiology, Vol. 78, Issue 23, p. 8421-8430
  • DOI: 10.1128/AEM.01983-12

Yeast Oligo-Mediated Genome Engineering (YOGE)
journal, November 2013

  • DiCarlo, James E.; Conley, Andrew J.; Penttilä, Merja
  • ACS Synthetic Biology, Vol. 2, Issue 12
  • DOI: 10.1021/sb400117c

Compartmentalization of metabolic pathways in yeast mitochondria improves the production of branched-chain alcohols
journal, February 2013

  • Avalos, José L.; Fink, Gerald R.; Stephanopoulos, Gregory
  • Nature Biotechnology, Vol. 31, Issue 4
  • DOI: 10.1038/nbt.2509

Combining the ‘two worlds’ of chemocatalysis and biocatalysis towards multi-step one-pot processes in aqueous media
journal, April 2014


Production of shikimic acid from Escherichia coli through chemically inducible chromosomal evolution and cofactor metabolic engineering
journal, January 2014

  • Cui, Yan-Yan; Ling, Chen; Zhang, Yuan-Yuan
  • Microbial Cell Factories, Vol. 13, Issue 1
  • DOI: 10.1186/1475-2859-13-21

Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield.
journal, January 1994


Chemical Routes for the Transformation of Biomass into Chemicals
journal, September 2007


Differential glucose repression in common yeast strains in response to HXK2 deletion
text, January 2010

  • Kümmel, Anne; Ewald, Jennifer Christina; Fendt, Sarah-Maria
  • Wiley-Blackwell
  • DOI: 10.5167/uzh-79180

Works referencing / citing this record:

Yeast factories for the production of aromatic compounds: from building blocks to plant secondary metabolites
journal, August 2016

  • Suástegui, Miguel; Shao, Zengyi
  • Journal of Industrial Microbiology & Biotechnology, Vol. 43, Issue 11
  • DOI: 10.1007/s10295-016-1824-9

Investigating strain dependency in the production of aromatic compounds in Saccharomyces cerevisiae: Strain Dependency in Producing Aromatic Compounds
journal, June 2016

  • Suástegui, Miguel; Guo, Weihua; Feng, Xueyang
  • Biotechnology and Bioengineering, Vol. 113, Issue 12
  • DOI: 10.1002/bit.26037

Iodine-Catalyzed Isomerization of Dimethyl Muconate
journal, May 2018


An expanded enzyme toolbox for production of cis, cis-muconic acid and other shikimate pathway derivatives in Saccharomyces cerevisiae
journal, February 2018

  • Brückner, Christine; Oreb, Mislav; Kunze, Gotthard
  • FEMS Yeast Research, Vol. 18, Issue 2
  • DOI: 10.1093/femsyr/foy017

The progress and outlook of bioelectrocatalysis for the production of chemicals, fuels and materials
journal, January 2020


Harnessing biocompatible chemistry for developing improved and novel microbial cell factories
journal, January 2020

  • Liu, Jian‐Ming; Solem, Christian; Jensen, Peter Ruhdal
  • Microbial Biotechnology, Vol. 13, Issue 1
  • DOI: 10.1111/1751-7915.13472

Modular Engineering of Biomass Degradation Pathways
journal, April 2019

  • Chaves, Julie E.; Presley, Gerald N.; Michener, Joshua K.
  • Processes, Vol. 7, Issue 4
  • DOI: 10.3390/pr7040230

Remodeling of the Photosynthetic Chain Promotes Direct CO 2 Conversion into Valuable Aromatic Compounds
journal, October 2018


Pathway engineering for the production of heterologous aromatic chemicals and their derivatives in Saccharomyces cerevisiae: bioconversion from glucose
journal, June 2017

  • Gottardi, Manuela; Reifenrath, Mara; Boles, Eckhard
  • FEMS Yeast Research, Vol. 17, Issue 4
  • DOI: 10.1093/femsyr/fox035

Structure Sensitivity in Hydrogenation Reactions on Pt/C in Aqueous‐phase
journal, October 2018


Tapping Renewables: A New Dawn for Organic Electrosynthesis in Aqueous Reaction Media
journal, April 2019


Biosensor-Enabled Directed Evolution to Improve Muconic Acid Production in Saccharomyces cerevisiae
journal, August 2017

  • Leavitt, John M.; Wagner, James M.; Tu, Cuong C.
  • Biotechnology Journal, Vol. 12, Issue 10
  • DOI: 10.1002/biot.201600687

Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products
journal, April 2018

  • Möhle, Sabine; Zirbes, Michael; Rodrigo, Eduardo
  • Angewandte Chemie International Edition, Vol. 57, Issue 21
  • DOI: 10.1002/anie.201712732

A Robust Strategy for Sustainable Organic Chemicals Utilizing Bioprivileged Molecules
journal, April 2019


Opportunities and challenges for combining chemo- and biocatalysis
journal, January 2018


Requirement of a Functional Flavin Mononucleotide Prenyltransferase for the Activity of a Bacterial Decarboxylase in a Heterologous Muconic Acid Pathway in Saccharomyces cerevisiae
journal, March 2017

  • Weber, Heike E.; Gottardi, Manuela; Brückner, Christine
  • Applied and Environmental Microbiology, Vol. 83, Issue 10
  • DOI: 10.1128/aem.03472-16

Identification of More Benign Cathode Materials for the Electrochemical Reduction of Levulinic Acid to Valeric Acid
journal, July 2019

  • Bisselink, Roel J. M.; Crockatt, Marc; Zijlstra, Martin
  • ChemElectroChem, Vol. 6, Issue 13
  • DOI: 10.1002/celc.201900734

Moderne Aspekte der Elektrochemie zur Synthese hochwertiger organischer Produkte
journal, April 2018

  • Möhle, Sabine; Zirbes, Michael; Rodrigo, Eduardo
  • Angewandte Chemie, Vol. 130, Issue 21
  • DOI: 10.1002/ange.201712732

Paired electrocatalytic hydrogenation and oxidation of 5-(hydroxymethyl)furfural for efficient production of biomass-derived monomers
journal, January 2019

  • Chadderdon, Xiaotong H.; Chadderdon, David J.; Pfennig, Toni
  • Green Chemistry, Vol. 21, Issue 22
  • DOI: 10.1039/c9gc02264c

Remodeling of the Photosynthetic Chain Promotes Direct CO 2 Conversion into Valuable Aromatic Compounds
journal, December 2018

  • Ni, Jun; Liu, Hong‐Yu; Tao, Fei
  • Angewandte Chemie International Edition, Vol. 57, Issue 49
  • DOI: 10.1002/anie.201808402

Engineering prokaryotic transcriptional activators as metabolite biosensors in yeast
journal, September 2016

  • Skjoedt, Mette L.; Snoek, Tim; Kildegaard, Kanchana R.
  • Nature Chemical Biology, Vol. 12, Issue 11
  • DOI: 10.1038/nchembio.2177