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

Suastegui, Miguel; Matthiesen, John E.; Carraher, Jack M.; Hernandez, Nacu; Rodriguez Quiroz, Natalia; Okerlund, Adam; Cochran, Eric W.; Shao, Zengyi; Tessonnier, Jean -Philippe

doi:10.1002/anie.201509653

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

Journal Article · Wed Jan 13 23:00:00 EST 2016 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201509653· OSTI ID:1239152

^[1]; ^[2]; ^[1]; ^[3]; ^[4]; ^[4]; ^[3]; ^[1]; ^[2]

Iowa State Univ., Ames, IA (United States); NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)
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)
Iowa State Univ., Ames, IA (United States)
NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)

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.

View Accepted Manuscript (DOE)

Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1239152

Report Number(s):: IS-J--8730

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 7 Vol. 55; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (45)

Fed-batch fermentor synthesis of 3-dehydroshikimic acid using recombinant Escherichia coli Li, Kai; Mikola, Mark R.; Draths, K. M. Biotechnology and Bioengineering, Vol. 64, Issue 1, p. 61-73 https://doi.org/10.1002/(SICI)1097-0290(19990705)64:1<61::AID-BIT7>3.0.CO;2-G	journal	July 1999
Engineering Catalyst Microenvironments for Metal-Catalyzed Hydrogenation of Biologically Derived Platform Chemicals Schwartz, Thomas J.; Johnson, Robert L.; Cardenas, Javier Angewandte Chemie, Vol. 126, Issue 47 https://doi.org/10.1002/ange.201407615	journal	September 2014
Biotechnologie von Morgen: metabolisch optimierte Zellen für die bio-basierte Produktion von Chemikalien und Treibstoffen, Materialien und Gesundheitsprodukten Becker, Judith; Wittmann, Christoph Angewandte Chemie, Vol. 127, Issue 11 https://doi.org/10.1002/ange.201409033	journal	February 2015
Engineering Catalyst Microenvironments for Metal-Catalyzed Hydrogenation of Biologically Derived Platform Chemicals Schwartz, Thomas J.; Johnson, Robert L.; Cardenas, Javier Angewandte Chemie International Edition, Vol. 53, Issue 47 https://doi.org/10.1002/anie.201407615	journal	September 2014
Advanced Biotechnology: Metabolically Engineered Cells for the Bio-Based Production of Chemicals and Fuels, Materials, and Health-Care Products Becker, Judith; Wittmann, Christoph Angewandte Chemie International Edition, Vol. 54, Issue 11 https://doi.org/10.1002/anie.201409033	journal	February 2015
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra ChemInform, Vol. 38, Issue 36 https://doi.org/10.1002/chin.200736263	journal	September 2007
Corrosion and its control Pletcher, Derek; Walsh, Frank C. Industrial Electrochemistry https://doi.org/10.1007/978-94-011-2154-5_10	book	January 1993
Downstream process for the production of yeast extract using brewer's yeast cells In, Man-Jin; Kim, Dong Chung; Chae, Hee Jeong Biotechnology and Bioprocess Engineering, Vol. 10, Issue 1 https://doi.org/10.1007/BF02931188	journal	February 2005
Development of new catalysts for N2O-decomposition from adipic acid plant Alini, Stefano; Basile, Francesco; Blasioli, Sonia Applied Catalysis B: Environmental, Vol. 70, Issue 1-4 https://doi.org/10.1016/j.apcatb.2005.12.031	journal	January 2007
Effect of biogenic fermentation impurities on lactic acid hydrogenation to propylene glycol Zhang, Zhigang; Jackson, James E.; Miller, Dennis J. Bioresource Technology, Vol. 99, Issue 13 https://doi.org/10.1016/j.biortech.2007.10.027	journal	September 2008
Combining the ‘two worlds’ of chemocatalysis and biocatalysis towards multi-step one-pot processes in aqueous media Gröger, Harald; Hummel, Werner Current Opinion in Chemical Biology, Vol. 19 https://doi.org/10.1016/j.cbpa.2014.03.002	journal	April 2014
Efficient Multiplexed Integration of Synergistic Alleles and Metabolic Pathways in Yeasts via CRISPR-Cas Horwitz, Andrew A.; Walter, Jessica M.; Schubert, Max G. Cell Systems, Vol. 1, Issue 1 https://doi.org/10.1016/j.cels.2015.02.001	journal	July 2015
Engineering yeasts for xylose metabolism Jeffries, Thomas W. Current Opinion in Biotechnology, Vol. 17, Issue 3, p. 320-326 https://doi.org/10.1016/j.copbio.2006.05.008	journal	June 2006
Metabolic engineering of yeast for production of fuels and chemicals Nielsen, Jens; Larsson, Christer; van Maris, Antonius Current Opinion in Biotechnology, Vol. 24, Issue 3 https://doi.org/10.1016/j.copbio.2013.03.023	journal	June 2013
Alleviation of feedback inhibition in Saccharomyces cerevisiae aromatic amino acid biosynthesis: Quantification of metabolic impact Luttik, M. A. H.; Vuralhan, Z.; Suir, E. Metabolic Engineering, Vol. 10, Issue 3-4 https://doi.org/10.1016/j.ymben.2008.02.002	journal	May 2008
Metabolic engineering of muconic acid production in Saccharomyces cerevisiae Curran, Kathleen A.; Leavitt, John M.; Karim, Ashty S. Metabolic Engineering, Vol. 15 https://doi.org/10.1016/j.ymben.2012.10.003	journal	January 2013
Biorefineries for the production of top building block chemicals and their derivatives Choi, Sol; Song, Chan Woo; Shin, Jae Ho Metabolic Engineering, Vol. 28 https://doi.org/10.1016/j.ymben.2014.12.007	journal	March 2015
Benzene-Free Synthesis of Adipic Acid Niu, W.; Draths, K. M.; Frost, J. W. Biotechnology Progress, Vol. 18, Issue 2, p. 201-211 https://doi.org/10.1021/bp010179x	journal	April 2002
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502 https://doi.org/10.1021/cr050989d	journal	June 2007
Bridging the Chemical and Biological Catalysis Gap: Challenges and Outlooks for Producing Sustainable Chemicals Schwartz, Thomas J.; O’Neill, Brandon J.; Shanks, Brent H. ACS Catalysis, Vol. 4, Issue 6 https://doi.org/10.1021/cs500364y	journal	April 2014
Yeast Oligo-Mediated Genome Engineering (YOGE) DiCarlo, James E.; Conley, Andrew J.; Penttilä, Merja ACS Synthetic Biology, Vol. 2, Issue 12 https://doi.org/10.1021/sb400117c	journal	November 2013
RNAi-Assisted Genome Evolution in Saccharomyces cerevisiae for Complex Phenotype Engineering Si, Tong; Luo, Yunzi; Bao, Zehua ACS Synthetic Biology, Vol. 4, Issue 3 https://doi.org/10.1021/sb500074a	journal	May 2014
Compartmentalization of metabolic pathways in yeast mitochondria improves the production of branched-chain alcohols Avalos, José L.; Fink, Gerald R.; Stephanopoulos, Gregory Nature Biotechnology, Vol. 31, Issue 4 https://doi.org/10.1038/nbt.2509	journal	February 2013
The battle for the “green” polymer. Different approaches for biopolymer synthesis: bioadvantaged vs. bioreplacement Hernández, Nacú; Williams, R. Christopher; Cochran, Eric W. Org. Biomol. Chem., Vol. 12, Issue 18 https://doi.org/10.1039/C3OB42339E	journal	January 2014
Adipic acid production from lignin Vardon, Derek R.; Franden, Mary Ann; Johnson, Christopher W. Energy & Environmental Science, Vol. 8, Issue 2 https://doi.org/10.1039/C4EE03230F	journal	January 2015
Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited Bozell, Joseph J.; Petersen, Gene R. Green Chemistry, Vol. 12, Issue 4, p. 539-554 https://doi.org/10.1039/b922014c	journal	January 2010
The battle for the “green” polymer. Different approaches for biopolymer synthesis: bioadvantaged vs. bioreplacement Hernández, Nacú; Williams, R. Christopher; Cochran, Eric W. Org. Biomol. Chem., Vol. 12, Issue 18 https://doi.org/10.1039/c3ob42339e	journal	January 2014
143. Polyene acids. Part V. Catalytic semi-hydrogenation of the three isomeric muconic acids and comfirmation of their configurations Elvidge, J. A.; Linstead, R. P.; Smith, John F. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9530000708	journal	January 1953
Lignin valorization through integrated biological funneling and chemical catalysis Linger, J. G.; Vardon, D. R.; Guarnieri, M. T. Proceedings of the National Academy of Sciences, Vol. 111, Issue 33, p. 12013-12018 https://doi.org/10.1073/pnas.1410657111	journal	August 2014
Engineering Escherichia coli coculture systems for the production of biochemical products Zhang, Haoran; Pereira, Brian; Li, Zhengjun Proceedings of the National Academy of Sciences, Vol. 112, Issue 27 https://doi.org/10.1073/pnas.1506781112	journal	June 2015
Customized optimization of metabolic pathways by combinatorial transcriptional engineering Du, Jing; Yuan, Yongbo; Si, Tong Nucleic Acids Research, Vol. 40, Issue 18 https://doi.org/10.1093/nar/gks549	journal	June 2012
Low Energy Electron Diffraction and Electron Spectroscopic Studies of the Oxidation and Sulphidation of Pb(100) and Pb(110) Surfaces Joyner, R. W.; Kishi, K.; Roberts, M. W. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 358, Issue 1693 https://doi.org/10.1098/rspa.1978.0006	journal	January 1978
Platform biochemicals for a biorenewable chemical industry Nikolau, Basil J.; Perera, M. Ann D. N.; Brachova, Libuse The Plant Journal, Vol. 54, Issue 4 https://doi.org/10.1111/j.1365-313X.2008.03484.x	journal	May 2008
Differential glucose repression in common yeast strains in response to HXK2 deletion: Differential glucose repression in common yeast strains Kümmel, Anne; Ewald, Jennifer Christina; Fendt, Sarah-Maria FEMS Yeast Research, Vol. 10, Issue 3 https://doi.org/10.1111/j.1567-1364.2010.00609.x	journal	April 2010
Yeast cell factories on the horizon Nielsen, J. Science, Vol. 349, Issue 6252 https://doi.org/10.1126/science.aad2081	journal	September 2015
Biosynthesis of cis, cis-Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae Weber, Christian; Brückner, Christine; Weinreb, Sheila Applied and Environmental Microbiology, Vol. 78, Issue 23, p. 8421-8430 https://doi.org/10.1128/AEM.01983-12	journal	September 2012
Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield. Patnaik, R.; Liao, J. C. Applied and Environmental Microbiology, Vol. 60, Issue 11 https://doi.org/10.1128/AEM.60.11.3903-3908.1994	journal	January 1994
CatM Regulation of the benABCDE Operon: Functional Divergence of Two LysR-Type Paralogs in Acinetobacter baylyi ADP1 Ezezika, O. C.; Collier-Hyams, L. S.; Dale, H. A. Applied and Environmental Microbiology, Vol. 72, Issue 3 https://doi.org/10.1128/AEM.72.3.1749-1758.2006	journal	March 2006
Transcriptional Repression Mediated by LysR-Type Regulator CatR Bound at Multiple Binding Sites Chugani, Sudha A.; Parsek, Matthew R.; Chakrabarty, A. M. Journal of Bacteriology, Vol. 180, Issue 9 https://doi.org/10.1128/JB.180.9.2367-2372.1998	journal	May 1998
Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway. Braus, G. H. Microbiological Reviews, Vol. 55, Issue 3 https://doi.org/10.1128/MMBR.55.3.349-370.1991	journal	January 1991
Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield. Patnaik, R.; Liao, J. C. Applied and Environmental Microbiology, Vol. 60, Issue 11 https://doi.org/10.1128/aem.60.11.3903-3908.1994	journal	January 1994
Purification and characterization of an oxygen-sensitive, reversible 3,4-dihydroxybenzoate decarboxylase from Clostridium hydroxybenzoicum. He, Z.; Wiegel, J. Journal of Bacteriology, Vol. 178, Issue 12 https://doi.org/10.1128/jb.178.12.3539-3543.1996	journal	June 1996
Production of shikimic acid from Escherichia coli through chemically inducible chromosomal evolution and cofactor metabolic engineering Cui, Yan-Yan; Ling, Chen; Zhang, Yuan-Yuan Microbial Cell Factories, Vol. 13, Issue 1 https://doi.org/10.1186/1475-2859-13-21	journal	January 2014
Development of an In Vitro Compartmentalization Screen for High-Throughput Directed Evolution of [FeFe] Hydrogenases Stapleton, James A.; Swartz, James R. PLoS ONE, Vol. 5, Issue 12 https://doi.org/10.1371/journal.pone.0015275	journal	December 2010
Differential glucose repression in common yeast strains in response to HXK2 deletion Kümmel, Anne; Ewald, Jennifer Christina; Fendt, Sarah-Maria Wiley-Blackwell https://doi.org/10.5167/uzh-79180	text	January 2010

Cited By (24)

Moderne Aspekte der Elektrochemie zur Synthese hochwertiger organischer Produkte Möhle, Sabine; Zirbes, Michael; Rodrigo, Eduardo Angewandte Chemie, Vol. 130, Issue 21 https://doi.org/10.1002/ange.201712732	journal	April 2018
Remodeling of the Photosynthetic Chain Promotes Direct CO ₂ Conversion into Valuable Aromatic Compounds Ni, Jun; Liu, Hong‐Yu; Tao, Fei Angewandte Chemie, Vol. 130, Issue 49 https://doi.org/10.1002/ange.201808402	journal	October 2018
Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products Möhle, Sabine; Zirbes, Michael; Rodrigo, Eduardo Angewandte Chemie International Edition, Vol. 57, Issue 21 https://doi.org/10.1002/anie.201712732	journal	April 2018
Remodeling of the Photosynthetic Chain Promotes Direct CO ₂ Conversion into Valuable Aromatic Compounds Ni, Jun; Liu, Hong‐Yu; Tao, Fei Angewandte Chemie International Edition, Vol. 57, Issue 49 https://doi.org/10.1002/anie.201808402	journal	December 2018
Biosensor-Enabled Directed Evolution to Improve Muconic Acid Production in Saccharomyces cerevisiae Leavitt, John M.; Wagner, James M.; Tu, Cuong C. Biotechnology Journal, Vol. 12, Issue 10 https://doi.org/10.1002/biot.201600687	journal	August 2017
Investigating strain dependency in the production of aromatic compounds in Saccharomyces cerevisiae: Strain Dependency in Producing Aromatic Compounds Suástegui, Miguel; Guo, Weihua; Feng, Xueyang Biotechnology and Bioengineering, Vol. 113, Issue 12 https://doi.org/10.1002/bit.26037	journal	June 2016
Structure Sensitivity in Hydrogenation Reactions on Pt/C in Aqueous‐phase Sanyal, Udishnu; Song, Yang; Singh, Nirala ChemCatChem, Vol. 11, Issue 1 https://doi.org/10.1002/cctc.201801344	journal	October 2018
Tapping Renewables: A New Dawn for Organic Electrosynthesis in Aqueous Reaction Media Harnisch, Falk; Schröder, Uwe ChemElectroChem, Vol. 6, Issue 16 https://doi.org/10.1002/celc.201900456	journal	April 2019
Identification of More Benign Cathode Materials for the Electrochemical Reduction of Levulinic Acid to Valeric Acid Bisselink, Roel J. M.; Crockatt, Marc; Zijlstra, Martin ChemElectroChem, Vol. 6, Issue 13 https://doi.org/10.1002/celc.201900734	journal	July 2019
Iodine-Catalyzed Isomerization of Dimethyl Muconate Settle, Amy E.; Berstis, Laura; Zhang, Shuting ChemSusChem, Vol. 11, Issue 11 https://doi.org/10.1002/cssc.201800606	journal	May 2018
A Robust Strategy for Sustainable Organic Chemicals Utilizing Bioprivileged Molecules Shanks, Brent H.; Broadbelt, Linda J. ChemSusChem, Vol. 12, Issue 13 https://doi.org/10.1002/cssc.201900323	journal	April 2019
Yeast factories for the production of aromatic compounds: from building blocks to plant secondary metabolites Suástegui, Miguel; Shao, Zengyi Journal of Industrial Microbiology & Biotechnology, Vol. 43, Issue 11 https://doi.org/10.1007/s10295-016-1824-9	journal	August 2016
Engineering prokaryotic transcriptional activators as metabolite biosensors in yeast Skjoedt, Mette L.; Snoek, Tim; Kildegaard, Kanchana R. Nature Chemical Biology, Vol. 12, Issue 11 https://doi.org/10.1038/nchembio.2177	journal	September 2016
Opportunities and challenges for combining chemo- and biocatalysis Rudroff, Florian; Mihovilovic, Marko D.; Gröger, Harald Nature Catalysis, Vol. 1, Issue 1 https://doi.org/10.1038/s41929-017-0010-4	journal	January 2018
The progress and outlook of bioelectrocatalysis for the production of chemicals, fuels and materials Chen, Hui; Dong, Fangyuan; Minteer, Shelley D. Nature Catalysis, Vol. 3, Issue 3 https://doi.org/10.1038/s41929-019-0408-2	journal	January 2020
Bioprivileged molecules: creating value from biomass Shanks, Brent H.; Keeling, Peter L. Green Chemistry, Vol. 19, Issue 14 https://doi.org/10.1039/c7gc00296c	journal	January 2017
Bioprocess development for muconic acid production from aromatic compounds and lignin Salvachúa, Davinia; Johnson, Christopher W.; Singer, Christine A. Green Chemistry, Vol. 20, Issue 21 https://doi.org/10.1039/c8gc02519c	journal	January 2018
Paired electrocatalytic hydrogenation and oxidation of 5-(hydroxymethyl)furfural for efficient production of biomass-derived monomers Chadderdon, Xiaotong H.; Chadderdon, David J.; Pfennig, Toni Green Chemistry, Vol. 21, Issue 22 https://doi.org/10.1039/c9gc02264c	journal	January 2019
Muconic acid production from methane using rationally-engineered methanotrophic biocatalysts Henard, Calvin A.; Akberdin, Ilya R.; Kalyuzhnaya, Marina G. Green Chemistry, Vol. 21, Issue 24 https://doi.org/10.1039/c9gc03722e	journal	January 2019
Pathway engineering for the production of heterologous aromatic chemicals and their derivatives in Saccharomyces cerevisiae: bioconversion from glucose Gottardi, Manuela; Reifenrath, Mara; Boles, Eckhard FEMS Yeast Research, Vol. 17, Issue 4 https://doi.org/10.1093/femsyr/fox035	journal	June 2017
An expanded enzyme toolbox for production of cis, cis-muconic acid and other shikimate pathway derivatives in Saccharomyces cerevisiae Brückner, Christine; Oreb, Mislav; Kunze, Gotthard FEMS Yeast Research, Vol. 18, Issue 2 https://doi.org/10.1093/femsyr/foy017	journal	February 2018
Harnessing biocompatible chemistry for developing improved and novel microbial cell factories Liu, Jian‐Ming; Solem, Christian; Jensen, Peter Ruhdal Microbial Biotechnology, Vol. 13, Issue 1 https://doi.org/10.1111/1751-7915.13472	journal	January 2020
Requirement of a Functional Flavin Mononucleotide Prenyltransferase for the Activity of a Bacterial Decarboxylase in a Heterologous Muconic Acid Pathway in Saccharomyces cerevisiae Weber, Heike E.; Gottardi, Manuela; Brückner, Christine Applied and Environmental Microbiology, Vol. 83, Issue 10 https://doi.org/10.1128/aem.03472-16	journal	March 2017
Modular Engineering of Biomass Degradation Pathways Chaves, Julie E.; Presley, Gerald N.; Michener, Joshua K. Processes, Vol. 7, Issue 4 https://doi.org/10.3390/pr7040230	journal	April 2019

Similar Records

Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis

Journal Article · Wed Oct 05 00:00:00 EDT 2016 · ACS Sustainable Chemistry & Engineering · OSTI ID:1355400

Bioenabled Platform to Access Polyamides with Built-In Target Properties

Journal Article · Fri May 06 00:00:00 EDT 2022 · Journal of the American Chemical Society · OSTI ID:1978472

cis,cis-Muconic acid: separation and catalysis to bio-adipic acid for nylon-6,6 polymerization

Journal Article · Thu Dec 31 23:00:00 EST 2015 · Green Chemistry · OSTI ID:1257542

Related Subjects

09 BIOMASS FUELS
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

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

Citation Formats

References (45)

Cited By (24)

Similar Records

Related Subjects