Implementation of Synthetic Pathways to Foster Microbe-Based Production of Non-Naturally Occurring Carboxylic Acids and Derivatives
Abstract
:1. Overview
2. Carboxylic Acids and Their Derivatives as “Green Building Blocks”
3. Implementation of New-to-Nature Pathways to Enable Microbe-Based Production of Naturally Occurring CAs
3.1. Glucaric Acid
3.2. Muconic Acid
4. A General View on the Implementation of Synthetic Pathways for the Production of Non-Naturally Occurring Compounds
5. Implementation of New-to-Nature Synthetic Pathways to Enable Microbe-Based Production of Adipic, Acrylic and Levulinic Acids
5.1. Adipic Acid
5.2. Acrylic Acid
5.3. Levulinic Acid
6. Bridging the Gap between CAs and Their More Economically Relevant Derivatives through the Assembly of Synthetic Pathways
6.1. Poly-Lactate Polymers
6.2. Methacrylic and Methyl-Methacrylic Acids
7. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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CA | Applications | Important Derivatives | Main Industrial Production Method | Microbe-Based Production Alternative |
---|---|---|---|---|
Malic | Detergents, food additives, pharmaceuticals, polyesters, solvents | Butanediol, THF, γ-butyrolactone | Hydration of maleic anhydride | Fermentation from renewable resources (Novozymes) using Aspergillus oryzae |
Succinic | Hydrogenation of maleic anhydride, maleic or fumaric | Fermentation at pilot scale using E. coli (BioAmber and Myrant), S. cerevisiae (Reverdia) and Basfia succiniciproducens (Succinity) | ||
Fumaric | Synthesis from butane-derived maleic | No industrial process established; production using fermentation with filamentous Fungi reported | ||
3-Hydroxypropionic | Superabsorbent, adhesives, surface coatings and paintings | Acrylates and 1,3-propanediol | Hydrolysis of 3-hydroxypropionitrile, hydrolysis of β-propiolactone and oxidation of 1,3- propanediol | No industrial process established; Fermentation from glucose or glycerol reported, mainly using E. coli and Klebsiella sp. |
Aspartic | Nutritional supplement in food and animal feed, sweeteners | Polyaspartic, aspartic anhydride, amine butanediol, amine THF, amine butyrolactone | Amination of fumaric acid (enzymatic or with immobilized cells), fermentation with E. coli or Coreynebacterium glutamicum | - |
Glucaric | Nylons and polyesters | Lactone, polyglucaric esters and amides | Chemical oxidation with nitric acid | Glucose fermentation using E. coli (Kalion) |
Glutamic | Food additive, potential new polymers | 1,5-propanediol, 1,5-propanediacid, 5-amino, 1-butanol | Glucose fermentation using C. glutamicum | - |
Itaconic | Rubber, solvents, acrylates, detergents, superabsorbents, drug delivery polymers, dental materials | MAA, MMA, polyesters, poly-itaconic acid polymers and styrene-butadiene | Glucose fermentation using Aspergillus terreus | - |
Levulinic | Solvents, polymers, acrylates, herbicides, photodynamic therapy | 2-methyl-THF, levulinate esters, 1,4-pentanediol, β-acetoacrylate, lactones, δ-aminolevulinic, diphenolic acid | Acid hydrolysis of crystalline sugars or lignocellulosic residues | No industrial process established; reported production from glucose using E. coli or an undefined microbial consortia |
Lactic | Biodegradable fibers in clothing, furniture and biomaterials | Lactate esters, propylene glycol, acrylates, poly-lactic acid | Fermentation of glucose from corn, cassava and sugarcane using Lactobacillus sp. | - |
Acetic | Food additive, solvent, fibers, filters, cellulose plastics and resins (used in paints, adhesives, coatings and textiles) | Vinyl acetate, acetic anhydride, acetate esters, monochloroacetic acid | Methanol carbonylation; liquid-phase oxidation of aliphatic hydrocarbons; fermentation using acetic acid bacterial (mainly in the vinegar industry) | - |
Citric | Acidulant, preservative, emulsifier, flavoring additive, sequestrant and buffering agent | - | Starch or glucose fermentation using A. niger | - |
Gluconic | Cleaning and construction industries, food additives including prebiotics | Glucono-lactone, sodium gluconate | Oxidation of glucose; Glucose fermentation using A. niger | - |
Adipic | Nylons and polyesters, plasticizers and lubricants | Esters for polymerization (PVC) | Synthesis from benzene | Fermentation of fatty acid rich-feedstocks (Verdezyne) or glucose (BioAmber) using yeasts (at a pilot scale) |
Acrylic | Various coatings (decorative, industrial, drug tablets, clothes), adhesives, polishes, carpet backing compounds | Methyl acrylate, ethyl acrylate, butyl acrylate and 2-ethylhexyl acrylate, polyacrylates | Oxidation of propene | Fermentation from renewable feedstocks (Arkema); Fermentation of dextrose and sucrose-based feedstocks (OPXBio and Dow) using E. coli (at pilot-scale) |
Glycolic | Tanning and dyeing agent for textiles, packaging materials | Polyglycolate, polyglicoside, butyl-glycolate | Catalysis from CO2 and formaldehyde and hydrolysis of chloroacetic acid | No industrial process established; reported production using E. coli (natural producer) or the yeasts S. cerevisiae and Kluveromyces lactis (engineered producers) |
Muconic | Plastics industry (automotive and packaging applications), synthetic fibers for textiles or industry (mainly nylon) and food acidifying agent | Adipic, terphthalic acid and trimellitic acid, caprolactam | Catalytic oxidation of cyclohexanol or cyclohexanol/cyclohexanone mixtures | No industrial process established; reported production from degradation of benzene-like xenobiotics and from glucose fermentation using Pseudomonas spp. (natural producers) and E. coli and S. cerevisiae (engineered hosts) |
Glucaric acid | Titer | Ref | |||||||||||||||||
Myo-inositol synthase (1) 5.5.1.4 | Myo-inositol oxygenase (2) 1.13.99.1 | Glucuronic acid dehydrogenase (3); 1.1.1.305 | |||||||||||||||||
E. coli | Scaffolded—S. cerevisiae Ino1 | Scaffolded—M. musculus MIOX | Scaffolded—P. syringae Udh | 2.5 g/L | [15] | ||||||||||||||
S. cerevisiae | Endogenous Ino1 | Stabilized Arabidopsis thaliana MIOX | P. syringae Udh | 6 g/L | [18] | ||||||||||||||
Muconic acid | Titer | Ref | |||||||||||||||||
From Dihydroshikimate | E. coli | Dihydroshikimate Hydratase (1); 4.2.1.118 Klebsiella pneumoniae aroZ | Protocatechuate decarboxylase (2) 4.1.1.63 K. pneumoniae aroY | Catechol 1.2-dioxygenase (3) 1.13.11.1 Acinetobacter calcoaceticus CatA | 38.6 g/L ● | [29] | |||||||||||||
S. cerevisiae | P. anserina aroZ | Talaromyces atroroseus GDC1 | A. radioresistens CatA | 1.24 g/L | [28] | ||||||||||||||
From chorismate | E. coli | Isochorismate synthase (8); 5.4.4.2 Endogenous EntC | Isochorismate pyruvate lyase (11); 4.2.99.21 P. fluorescens PchB | Salicylate monoxygenase (12); 1.14.13.1 P. putida nahG | Catechol 1.2-dioxygenase (3) 1.13.11.1 P. putida CatA | 1.5 g/L | [30] | ||||||||||||
From anthranilate | E. coli | Anthranilate 1.2-dioxygenase (14) 1.14.12.1 P. aeruginosa AntABC | Catechol 1.2-dioxygenase (3) 1.13.11.1 P. putida CatA | 389.96 mg/L | [30] | ||||||||||||||
From tyrosine | E. coli | Tyrosine phenol lyase (15);4.1.99 Citrobacter brakii tutA | Phenol hydrolyase (7)1.14.13.7 P. steutzeri PhKLMOP | Catechol 1.2-dioxygenase (3) 1.13.11.1 P. putida CatA | 186 mg/L | [31] | |||||||||||||
Adipic acid | Titer | Ref | |||||||||||||||||
Reverse adipate route | S. cerevisiae | 3-Oxoadipyl-CoA thiolase (1); 2.3.1.174 T. fusca Tfu_0875 | 3-Hydroxyadipyl-CoA dehydrogenase (2) 1.1.1.35 T. fusca Tfu_2399 | 2,3-Dehydroadipyl-CoA hydratase (3); 4.2.1.17 T. fusca Tfu_0067 | Adipyl-CoA dehydrogenase (4);1.1.1.35 T. fusca Tfu_1647 | Adipyl-CoA thioesterase (5) T. fusca Tfu_2577 and 2576 | 3.83 mg/L | [32] | |||||||||||
Reverse β-oxidation followed by ω-reduction * | E. coli | 3-ketoacyl-CoA thiolase (6)2.3.1.16 C. necator BktB | Trans-enoyl-CoA reductase (7) 1.3.1.44 E. gracilis Ter | ω-Hydroxylase (8) 1.14.15.3 P. putida AlkBGT | Alcohol dehydrogenase (9) * Acinetobacter spp. ChnD | Aldehyde dehydrogenase (10) * Acinetobacter spp. ChnE | - | [33] | |||||||||||
2-oxopimelic route | E. coli | 2-oxoglutaric elongation to 2-oxopimelic (11) A. vinelandii nifV (2.3.3.14) and M. aeolicus Nankai AksD (4.2.1.114), AksE (4.2.1.33), and AksF * | 2-Oxopimelic decarboxylase (12)4.1.1.72 Lactococcus lactis KdcA | Adipic semi-aldehyde oxidation (13) Unknown endogenous enzyme | 0.3 g/L | [34] | |||||||||||||
From muconic acid | S. cerevisiae | DHS hydratase 4.2.1.118 P. anserina aroZ | Protocatechuate decarboxylase; 4.1.1.63 Enterobacter cloacae aroY | Catechol 1,2-dioxygenase1.13.11.1 C. albicans HQD2 | Enoate reductase(22)1.3.1.31 Bacillus coagulans MAR (MAR-BC) | 2.6 mg/L | [35] | ||||||||||||
Acrylic acid | Titer | Ref | |||||||||||||||||
From glycerol | E. coli | Glycerol-3-P phosphatase3.1.3.21 S. cerevisiae Gpp2 | Glycerol Dehydratase 4.2.1.30 K. pneumoniae DhaB | Aldehyde Dehydrogenase 1.2.1.16 C. necator GabD4 | CoA transferase 2.8.3.8 C. necator YdiF | CoA dehydratase* A. flavithermus Aflv_0566 | 0.12 g/L | [36] | |||||||||||
Levulinic acid | Titer | Ref | |||||||||||||||||
From 3-oxoadipic | E. coli | Succinyl-CoA transferase 2.8.3.18 C.kluyveri Cat1 | β-ketoadipyl-CoA thiolase (1) 2.3.1.174 Endogenous PaaJ | 3-Oxoadipyl-CoA transferase (2); 2.8.3.6 P. putida PcaIJ | 3-Oxoadipic acid decarboxylase (3);4.1.1.4 C. acetobutylicum Adc | 159 mg/L | [37] | ||||||||||||
PCA synthesis (4) P. putida Fcs (6.2.1.34), Ech (4.1.2.61), Vdh (1.2.1.67), VanAb (1.14.13.82), PobA (1.14.13.2) | Dearomatization pathway (5) P. putida PcaGH (1.13.11.3), PcaB (5.5.1.2), PcaC (4.1.1.44), PcaD (3.1.1.24) | 3-Oxoadipic Acid decarboxylase (3); 4.1.1.4 C. acetobutylicum Adc | 455 mg/L | [38] | |||||||||||||||
Methacrylic acid | Titer | Ref | |||||||||||||||||
Through Isobutyryl-CoA | E. coli | Isobutyryl-CoA synthase (1) 6.2.1.3 P. chlorpraphis AcsA | Acyl-CoA oxidase (2); 1.3.3.6 A. thaliana ACX4 | Hydroxybenzoyl-CoA thioesterase (3); 3.1.2.23 Arthrobacter spp. 4HBT | ~250 µM | [39] |
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Vila-Santa, A.; Mendes, F.C.; Ferreira, F.C.; Prather, K.L.J.; Mira, N.P. Implementation of Synthetic Pathways to Foster Microbe-Based Production of Non-Naturally Occurring Carboxylic Acids and Derivatives. J. Fungi 2021, 7, 1020. https://doi.org/10.3390/jof7121020
Vila-Santa A, Mendes FC, Ferreira FC, Prather KLJ, Mira NP. Implementation of Synthetic Pathways to Foster Microbe-Based Production of Non-Naturally Occurring Carboxylic Acids and Derivatives. Journal of Fungi. 2021; 7(12):1020. https://doi.org/10.3390/jof7121020
Chicago/Turabian StyleVila-Santa, Ana, Fernão C. Mendes, Frederico C. Ferreira, Kristala L. J. Prather, and Nuno P. Mira. 2021. "Implementation of Synthetic Pathways to Foster Microbe-Based Production of Non-Naturally Occurring Carboxylic Acids and Derivatives" Journal of Fungi 7, no. 12: 1020. https://doi.org/10.3390/jof7121020